As a child, Rumplestiltskin watches his father, Malcolm, swindle a participant out of money in a rigged card game and then get beat up for it, though he tries to intervene to protect his only parent. The man steals Malcolm's money, leaving both father and son penniless. Rumplestiltskin is sent to a pair of wool spinners while his father goes off to look for work. Reluctant to be left behind, he is consoled when presented with a straw doll by his father. Urged by his father to name the doll so it can be his protector, Rumplestiltskin chooses "Peter Pan". For the duration of his stay, he becomes quite good at spinning wool; earning praise from the spinsters. They suggest he can spin for kings and queens one day. Pleased, Rumplestiltskin envisions earning money so he and his father can be together. The spinsters state Malcolm's reputation as a cheat and coward will never die down. They hand Rumplestiltskin a magic to take himself to another land, and reveal his father is continuing to swindle people out of money. In disbelief, Rumplestiltskin goes to find his father at the pub. Despite his father's terrible ways, Rumplestiltskin suggesting they start afresh together by using a magic bean. Malcolm recalls the phrase "think lovely thoughts", which he often said to himself at night during his difficult childhood years, and traveled to a wonderful place called Neverland in his dreams.
They use the bean to reach Neverland, where Malcolm quickly realizes he can no longer fly as he did in his boyhood years, and proposes they look for pixie dust so the feat is possible again. Rumplestiltskin waits beneath the tree as his father climbs up. A moment later, Malcolm gives up on his dream of flying because adults don't belong in Neverland, so Rumplestiltskin advises they can try another land as all that matters is being together. Rather than that, Rumplestiltskin is grabbed by the Shadow, but manages to hold onto his father, who reveals he wants to stay in Neverland alone and regain youth. Rumplestiltskin is let go by Malcolm and whisked up higher as he drops his doll and watches his father transform into a young boy. Dropped back home, Rumplestiltskin seeks comfort at the spinsters' cottage as he cries over his father's abandonment. The spinsters offer him a home with them. On a lesser level, Rumplestiltskin is upset his doll, Peter Pan, is gone forever. ("Think Lovely Thoughts")
When Rumplestiltskin is older, he marries a woman named Milah, and together they live in a village spinning and selling wool. One day, he is drafted to fight in the ogre war; excited to prove himself and show that he is not a coward like his father. However, in the training camp, the prisoner he is assigned to watch over as his first task—a Seer—indicates she knows of his fate, and would gladly exchange this information for a glass of water. She tells him that Milah is pregnant, and that his actions on the battlefield will leave his son fatherless. Skeptical at first, Rumplestiltskin eventually believes what she says and intentionally injures himself, so that he can get out of the war and be with his son, Baelfire. Once he returns home, Rumplestiltskin attempts to explain to Milah about the seer's prophecy, but she is astonished that he is gullible enough to believe in such a thing. Disgusted with his cowardice, she argues it would have been much more honorable for him to die and for Baelfire to have a dead father that fought in the war. ("Manhattan")
As the years pass, Milah grows more and more disillusioned and unhappy with the life she has with Rumplestiltskin. She drinks and gambles at the bar with a pirate captain, Killian Jones, and his ship crew men. He comes by to bring Milah home, to which she jeers and mocks him for his cowardly reputation. From outside, Baelfire comes in asking for his mother, and only then does Milah depart for her son's sake. At home, Milah tries to persuade Rumplestiltskin that it's possible for them to have a better life in another place where he doesn't have to live in the shadow of his reputation and they can travel the world. Instead, Rumplestiltskin pushes her to make the marriage work for Baelfire. She reluctantly agrees, but the next morning, he hears word of Milah's kidnapping by Killian. Rumplestiltskin attempts to rescue his wife, but is turned away by Killian when he is too cowardly to duel with him. Regretfully, he returns home to tell Baelfire that his mother is dead. ("The Crocodile")
When the kingdom resorts to using children as soldiers in yet another ogre war, Rumplestiltskin and his son flee into the forest, only to be found and bullied by royal knights. After the knights leave, Rumplestiltskin and Baelfire are approached by a mysterious old man who offers them help in exchange for a small amount of food and company. After Rumplestiltskin explains his reason for running away, the old man has a better idea and steers him towards stealing a magical dagger from the Duke's castle. As holder of the dagger, Rumplestiltskin can control the Dark One, a terrifying entity with unmatched magical powers who is the most feared being in all the land. He decides to steal the dagger with the hopes of protecting Baelfire and turning the Dark One into a force of good. However, Rumplestiltskin can't see himself keeping the Dark One as a slave as he is terrified of him. Convinced he has no other choice, Rumplestiltskin sets fire to the Duke's castle and makes off with the blade. Afterwards, he meets Baelfire in the forest and sends him home. Once alone, Rumplestiltskin summons the Dark One and cowers at the being's presence. When the Dark One taunts him about Baelfire not truly being his son, Rumplestiltskin stabs the entity in a fit of blind rage. Shockingly, he discovers the Dark One is the old man who told him about the dagger. The man briefs on all the horrible deeds he was forced to do as the Dark One and states death is welcome release and ominously warns Rumplestiltskin that "magic always comes with a price". Then, Rumplestiltskin's own name replaces Zoso's on the dagger, and he gains the powers of the Dark One. Relishing over his new-found status, he returns home to humiliate and kill the knights who harassed him and his son while Baelfire looks on in terror. ("Desperate Souls")
As Rumplestiltskin continues his reign as the Dark One, he doesn't allow Baelfire out of the house. One day, he gifts his son a knife, but Baelfire angrily proclaims he wants nothing his father gains from being the Dark One. The boy desires freedom to go out and have friends, although Rumplestiltskin forbids it since his enemies might kidnap him. Baelfire thinks his father is afraid he'll choose to leave and never return, which Rumplestiltskin denies and asserts he's simply concerned for his son's safety. The next day, after procuring a castle for Baelfire, Rumplestiltskin returns home to find his son missing. Investigating at the nearby town of Hamelin, the townspeople admit to the Dark One that all their children are gone, and they suspect someone playing a pan flute from the prior night led them away. On the next night, Rumplestiltskin watches as several boys are guided by the distant sound of a pan flute to a campfire, where many are fervently dancing around in animal masks. Unable to find Baelfire, he confronts the cloaked piper by snapping the pan flute in half. As the stranger takes off his hood, a shocked Rumplestiltskin learns the piper is Peter Pan, his father who abandoned him for youth. Pan admits it's lonely in Neverland and he desires some companions. Since only certain boys filled with loneliness can hear the pan flute, he points out this is why Rumplestiltskin heard it as well. His father accuses him of craving power, but in actuality, is nothing more than an unloved, lonely lost boy. Recalling his son's abandonment issues, Pan challenges Rumplestiltskin to put his trust in Baelfire and allow him to stay or leave out of free will. Rumplestiltskin ignores the suggestion and whisks Baelfire to safety with magic. At home, Rumplestiltskin attempts to help Baelfire see how dangerous Pan is by briefly disclosing he once knew him, but the latter betrayed him in the end. Even so, Baelfire reveals knowing about the Pan offered earlier, and he angrily asserts had Rumplestiltskin asked him, his choice would have been to stay. As Baelfire contemplates their lost chance to be a family, Rumplestiltskin says they still can, though his son storms out abruptly. ("Nasty Habits")
Eager to fulfill his promise, Rumplestiltskin puts his new found powers to use by bringing about an end to the ogre war by walking into the middle of battlefields and brokering a truce between the warring parties. However, while this good deed brings Rumplestiltskin reverence and respect, the powers of the Dark One have corrupted his mind, causing him to continually hurt people and seek more power for fear that he would not be able to protect Baelfire from his enemies otherwise. As a downside, people begin to fear him, especially after Rumplestiltskin publicly demonstrates cruelty towards a peddler after Baelfire injuries his knee running into the man's wagon. Though Baelfire believes his father would not need so much power if he simply did not have any, Rumplestiltskin details the only way to rid himself of the Dark One's abilities is if someone killed him with the dagger. In a deal, Rumplestiltskin agrees to give up his powers, if there is way to do so without dying, if Baelfire can find a way. Baelfire comes back home with a magic bean given to him by the Blue Fairy so they can both go to a land without magic, thus making Rumplestiltskin without his powers. However, when the a portal is opened for them to jump into, Rumplestiltskin backs out of his promise to Baelfire, clinging onto his son's hand while the dagger keeps himself from falling in, until he finally lets go of Baelfire as the vortex closes. When he finally comes to terms with the fact his son is gone, Rumplestiltskin furiously calls the Blue Fairy and begs her to send him to Baelfire. She says it is impossible to do without any magical means, and accidentally lets it slip that a powerful curse can bring him to his son. From this point on, Rumplestiltskin vehemently swears to stop at nothing, even if it means sacrificing an entire world, to reunite with his beloved Baelfire. ("The Return")
Since Rumplestiltskin's loss of his son, the seer, now much older, appears before him once more and proclaims the future she foresaw for him many years ago has recently come to pass. With magical force, he demands information out of her about how to reach his son. Eventually, she allows him to take her powers so that he may learn to see into the future. By doing so, the burden of future sight is no longer in her hands. Just as the seer is drawing her last breaths of life, she sees into his future one last time. She speaks of how he find his son under the most unusual of circumstances, and a young boy who will be the key to the reunion. Alas, this boy will also be his undoing. Despite her warning, he doesn't see the boy as a true threat and decides to kill him when the time comes. ("Manhattan")
A time gap passes, and Rumplestiltskin is promised a magic bean by a man named William Smee. Rumplestiltskin agrees and promises the man eternal life in exchange, but if the bargain is not met, he will age him to dust. Before leaving the bar, Rumplestiltskin sees Killian Jones enter with his crew and stays to follow after them. In the alley outside the bar, Rumplestiltskin passes them and the pirates proceed to mock him. When Rumplestiltskin reveals himself, Killian recognizes him as the coward from his ship, but also as the Dark One. They begin a duel, with Killian nearly having his heart ripped out by Rumplestiltskin, until a very much alive Milah pleads on the pirate's behalf. He learns the truth of Milah's disappearance all those years ago, that the kidnapping was nothing but a cover story, and she willingly went with Killian because they fell in love. Rumplestiltskin is furious, but Milah offers him Smee's magic bean in exchange for both Killian's life as well as her own. They meet aboard Killian's ship the next day to seal the deal. Unable to hold back his inquiries, he questions Milah's judgement in leaving their son behind. Milah admits feeling guilty about her choice, which she made while miserable in the marriage with Rumplestiltskin. As the argument heats up, she denies ever loving him, causing Rumplestiltskin to rip out her heart out of rage. While Killian cradles a dying Milah in his arms, Rumplestiltskin crushes her heart to ash. Then, he procures the magic bean by cutting off Killian's clenched left hand. Though Killian stabs him with a hook, it has no effect on Rumplestiltskin, who departs unharmed. When he finally checks the severed hand, he discovers the bean is missing. ("The Crocodile")
In a deal with Jiminy, who wishes to be free of his parents, Martin and Myrna, Rumplestiltskin gives him a potion to transform them into another form. However, Jiminy's parents switch the potion to give it to a village couple, Stephen and Donna, which converts them into puppets. Afterwards, the puppets are retained in Rumplestiltskin's possession within his castle. ("That Still Small Voice")
Driven by a future vision, Rumplestiltskin approaches a miller's daughter, Cora, who lied to King Xavier about her skill for spinning straw into gold and now must prove herself or she'll be faced with death. Rumplestiltskin agrees to help if she gives him her first-born child, who will have great importance in the future he foresees. She agrees, but only if he teaches her to spin straw into gold. He instructs that the key to making magic work is to give into the rage of emotion she feels at her worst moment. They bond over their similar, humiliating experiences. Her anger channels into magic, and turns the straw into gold. After Cora wins the hand of King Xavier's son, Rumplestiltskin visits her on the day before the wedding where they share a passionate kiss. Despite being fifth-in-line to the throne once she marries the prince, she has a change of heart and wants have genuine love with Rumplestiltskin. He decides to change the deal so any child they have together will be his. Cora readily agrees, but wants to learn how to rip out a heart, so she can have revenge on King Xavier. Following this lesson, they settle on meeting under a tree in the castle courtyard after Cora extracts King Xavier's heart in a box, and then they will run away together. When she finally arrives, Cora goes back on their agreement as power is more important to her than love. Puzzled, he asks whose heart is in the box. Saddened, Cora admits it is hers as it is necessary to remove the love she has for him to focus on obtaining power. Infuriated at the betrayal, he demands payment for their deal, but Cora reminds him of the changed contract, and any child she has will never be his. ("The Miller's Daughter")
Travelling from Arendelle to the Enchanted Forest, a woman named Ingrid asks Rumplestiltskin to permanently get rid of her ice powers. Ingrid desires to be normal as magic is not common in Arendelle, and even when Rumplestiltskin offers to teach her to harness them, she refuses. He implies that the true love existing between Ingrid and her sisters, Helga and Gerda, is equal in weight to magic and might be enough to help her. However, Ingrid persuades him that her powers are too strong and she absolutely needs something to control them. He shows them a pair of gloves capable of concealing magic, but only if she has faith. As a safety measure, he directs them to an urn to entrap Ingrid if her powers grow too dangerous. When Ingrid attempts to take the items from him, Rumplestiltskin explains their deal requires an exchange of goods, so he asks for the sisters' three ribbons. Though they look like ordinary objects, even the simplest things can contain magic because of the essence of love. Helga and Gerda dislike the idea, believing they can protect Ingrid on their own, but their sister goes through with the deal to ensure she will never harm anyone with her powers. ("The Snow Queen")
In another kingdom, King George finds himself unable to bear an heir after his wife is cursed to be barren. Rumplestiltskin finds a farm where a commoner, Ruth, has recently given birth to twin boys. Granted permission by both her and her husband, he takes one of the children to be raised as King George's heir in exchange for keeping the farm afloat with monetary support. ("The Shepherd")
One evening, Rumplestiltskin is summoned by Regina, the daughter of Cora, when she accidentally says his name out loud from her mother's spell book. He exhibits knowledge about who she is as their families know each other in the past and future. To his surprise, Regina is a sweet-natured woman who doesn't wish to hurt anyone, particularly when he suggests she can kill Cora. He shows Regina a magic mirror to another world and tempts her into getting rid of Cora with a simple push into it. On the day of the wedding, Rumplestiltskin manifests inside the mirror reflection to beckon Regina into going through with their plan, to which she obeys. Now free of her mother, she returns the spell book to Rumplestiltskin on her way out of the kingdom. Though Regina insists she doesn't need magic, he continually prods her over how it felt using magic. She admits, with much hesitancy, that she loved it, but has fears of turning out like her magic-obsessed mother. Rumplestiltskin promises that is entirely up to her, and takes Regina in as a magic protege. ("We Are Both")
To start with, he instructs Regina how to conjure a rock, which she has difficulties learning. Rumplestiltskin later spies on her mastering this technique, but upon closer look, it is actually a red-haired woman donning Regina's clothes. The woman, Zelena, claims to be Cora's first-born child; something he refuses to believe until testing her genetics. Surprised by the unexpected, Rumplestiltskin teaches her magic, as he did with Cora, by helping her channel rage into power. As a cooling down period after exerting this much magical force, she is taught to think of a happy memory. When Zelena asks for an example, he tells her of his time growing up with spinsters who baked him meat-pies. Sometime following this, Rumplestiltskin send a letter to Cora about his discovery of Zelena, who he believes is even more powerful than her. After the lesson, Zelena makes him a meat-pie, but he cannot stay since Regina still needs his help learning magic. At this, an angered Zelena repeatedly insists she is casting his curse so he doesn't need Regina, to which Rumplestiltskin points out that her jealousy is literally turning her skin green. Realizing the potential danger, he masquerades as Regina to bait Zelena, who tries to kill her half-sibling. He disqualifies her from casting his curse since one one of the spell's main ingredients is the thing she loves most—him—and that makes her too dangerous. However, Rumplestiltskin is quick to change his mind after Zelena mentions she has a pair of slippers that can take him to a Land Without Magic. Zelena scornfully rejects his offer, and before disappearing, she promises that next time he will choose her. Soon after, Regina succeeds in conjuring the rock, which pleases Rumplestiltskin so much he dubs her his "best pupil". Furious, Zelena witnesses the exchange from Oz. ("It's Not Easy Being Green")
The lesson moves onto teaching Regina to manifest a ball of fire. After he demonstrates, she copies him, but has problems keeping the fire from burning out. Zelena, who is continuing to spy on them from Oz, angrily remarks it's not that difficult, and as proof, she creates a massive fireball of her own. ("Kansas")
Continuing to train Regina in the dark arts, Rumplestiltskin teaches her to rip out a horse's heart, but she refuses to do it. Annoyed by her hesitation, he tells Regina to figure out what is holding her back. He discovers she is still pining after her dead fiancé, though it is not possible to bring someone back with magic. Instead, he does a bit of research by traveling to the Land Without Color to witnesses a doctor, Victor Frankenstein attempting to retrieve his brother from the dead. They come to a deal for Victor to teach him knowledge on revival while Rumplestiltskin leaves behind a horde of gold for him as payment. He comes to Victor again after the doctor's failure at revival because of scorching his brother's heart. Rumplestiltskin guarantees him a stronger heart if he will help fake a failed attempt to restore Regina's deceased lover. The doctor agrees, and Rumplestiltskin returns to the Enchanted Forest to turn Regina away from magic lessons since she can't let go of the past. At the same time, Rumplestiltskin procures items from a world traveler, Jefferson. Unknown to Regina, the two are working together to push her to call on Victor to resurrect her fiancé. Victor follows the terms of Rumplestiltskin's deal to crush Regina's hopes of regaining her past. Directly after, Rumplestiltskin takes on a new magic apprentice, Trish, though Regina cuts the lessons short by tearing out and crushing the girl's heart to prove to Rumplestiltskin she is ready for the dark arts. Satisfied with the end result, Rumplestiltskin takes her back, and in secret, gives Victor a heart as promised. They have a disagreement about the usefulness of magic, though Rumplestiltskin is quite certain Victor will discover magic is indeed beneficial. ("The Doctor", "In the Name of the Brother")
Regina resumes her magic lessons with Rumplestiltskin, but does not show up for one planned session. That night, while she is dining alone, he materializes in the seat across the table from hers. Regina voices concerns about continuing the lessons as she doesn't want her own future to end up like his, and when prompted, goes on the detail the unhappiness in her life. She talks about being Queen as well as feeling like a prisoner in a castle, having a husband whose only focus is on his dead wife and young daughter. With no freedom, she finds life intolerable. Rumplestiltskin interjects that leaving this life is not possible even though Regina thinks there are choices in having love or darkness. He states what she doesn't know is that darkness is what will consume her. Upset at his words, Regina orders him to leave. Instead, Rumplestiltskin explains further that once the darkness has started to eat away at her, it will progress until she is swallowed whole, and there's no way to fly away from fate. Before leaving, he sets up lessons for tomorrow and stresses she must bring the only thing inside herself, which is simmering rage. ("Quite a Common Fairy")
When Rumplestiltskin's magic lessons come to a halt, Regina angrily complains to him about it. He advises her to have more patience, and uses Maleficent, who spent years honing her powers, as a good example. However, after she insinuates he is not skilled enough to teach her, he whisks Regina to Maleficent for assistance instead. Surprisingly, Regina returns, with a small dose of the sleeping curse, which she tests on Snow White's precious horse. Since spending time with Maleficent, Regina considers that Rumplestiltskin was right about being patient, and she promises not to question his teachings from now on. ("Enter the Dragon")
Through a crystal ball, Rumplestiltskin looks into Ruth's farm where her remaining son, David, is now a shepherd. With Ruth's knowledge, a farm visitor named Joan receives the name of a wizard who can help her with something magic-related. As Joan rides away on her journey, she looks at the slip of paper where Ruth had written the wizard's name. When she attempts to enunciate his name, Rumplestiltskin, the Dark One himself sees this from his crystal ball and cackles in delight. Despite the name she presented herself with to David and Ruth, Rumplestiltskin already knows her true name is Anna and she has come to seek answers about her parents' past reason for coming to the Enchanted Forest. ("White Out", "The Apprentice")
Learning of a sorcerer's box with the ability to absorb magic, Rumplestiltskin decides to obtain it to be free of the dagger's will but also keep his Dark One powers. First, he poisons the apprentice guarding the box. Then, with good timing, Rumplestiltskin strikes a deal with Anna; sending her to douse the apprentice's tea with a bottled substance. While it is an antidote to cure poison, Rumplestiltskin is simply testing Anna, who believes the substance is lethal, as he knows she won't do it. In the end, he reveals the truth and shows her the apprentice's reversion into a mouse. While Anna runs off to the man's cottage, Rumplestiltskin materializes there as well. Since she broke the contract, her punishment is to be locked up in his castle forever. Because of the box's second line of defense, in which it can only be touched by one who has been tempted by darkness but hasn't succumbed to it, he goads Anna into acting against her kind-hearted nature. Desperate, Anna threatens him with a sword as he insists she has to kill him in order to walk away. Following a terse moment, she collapses in tears. One of her tears drips onto Rumplestiltskin's dagger, which he takes to breach the box's second line of defense and gain the box. He tells Anna about her parents, fearful of Elsa's powers, wanted to be rid of it with the box's power of absorbing magic. However, Rumplestiltskin's ulterior motives for the box are spoiled when the apprentice, in mouse form, bites him. This causes him to drop the dagger, which Anna grabs. With it, she forces him to hand over the box. She then orders Rumplestiltskin to do three things—return her and the box to Arendelle, never harm her or Elsa and revert the apprentice into a human. After she is sent away, the dagger falls to the floor, which Rumplestiltskin retrieves and proceeds to rage at his failure. ("The Apprentice")
Desperate to have another family, Ingrid uses a spell to turn Anna against Elsa. However, she did not anticipate that Anna would seal Elsa in the urn. An enraged Ingrid then freezes all of Arendelle, to which Rumplestiltskin appears before her asking for the sorcerer's hat. Though she claims not to know where it is, Rumplestiltskin takes away the urn and will only return it when he has the hat. Before leaving, he instructs her to summon him, by calling his name thrice, once she is ready. Later, Ingrid changes her mind and gives the hat to the sorcerer's apprentice in exchange for finding another person she intends to make part of her family. ("Smash the Mirror")
Desiring to acquire a curse hidden in the Bald Mountain, which has three obstacles and is guarded by a fearsome Chernabog, he uses Cruella De Vil, Maleficent and Ursula to accomplish this. Sending invitations to Cruella and Ursula to meet at the Forbidden Fortress, the women arrive and bicker with Maleficent, who is unhappy about having strangers in her home. Rumplestiltskin then reveals he sent the invitations and proposes the trio help him retrieve a curse, which can grant all of them happy endings that they'd otherwise be unable to have as villains. After agreeing, they travel with him to the Bald Mountain, where Cruella and Maleficent uses their magical abilities to take down one obstacle per person, until Ursula grabs the curse with her tentacles. This triggers the Chernabog into attacking, and as Rumplestiltskin confesses to the truth, he advises them to be wary of the demon's power to detect the heart of the person who has the greatest potential for evil and devour it. Since he intended for all three to die at the Chernabog's hands, he quickly exits the room and out of the mountain as the women fight to escape the beast. ("Darkness on the Edge of Town")
Some time later, Rumplestiltskin has amassed considerable wealth and a castle of his own. Summoned by Sir Maurice to protect his town from a horde of ogres, the Dark One makes a deal to protect the kingdom in exchange for Maurice's daughter, Belle, to live in his castle forever as a caretaker. To protect her family and the people on the lands, she agrees to go with him. ("Skin Deep")
Desiring a skilled thief to help him steal the elixir of the wounded heart from Zelena, Rumplestiltskin tempts Robin Hood in exchange for clearing his taxes. Through a portal, Robin Hood heads to Oz to retrieve the item, but he ends up forfeiting the elixir to someone else who needs it more than him. Having stolen a six-leaf clover from Oz, Robin Hood decides to use it to glamour himself if he and the Dark One ever meet again so Rumplestiltskin won't harm him for breaking their deal. ("Heart of Gold")
Annoyed at Belle's nightly crying sessions because of missing her family, he bursts in, conjuring a pillow so she can muffle her sobs, which are distracting him from his spinning. Suddenly, they discover a hooded thief stealing a wand. Unbeknownst to Rumplestiltskin, the thief is actually Robin Hood glamored to look like another man. Caught in the act, the thief shoots an arrow from his enchanted bow at the Dark One, hitting him in the chest. The arrow, however, has no effect on Rumplestiltskin, who imprisons the thief. After flogging his prisoner, he leaves the castle and later returns to find Belle let him go. Furious, Rumplestiltskin forces her to come along so she can watch him kill the thief. On the carriage ride there, Belle tries to talk him out of murder so people will see he is a man, not a beast. While she believes he loves something more than power, Rumplestiltskin cackles that he loves his things most of all. In the woods, the Sheriff of Nottingham recognizes the thief's bow that Rumplestiltskin is carrying, but before providing any information, he asks to spend a night with Belle. Rumplestiltskin refuses, and when the latter continues to press the issue, he menaces the Sheriff by ripping out his tongue. After regaining his tongue, the Sheriff finally admits the thief's name is Robin Hood and discloses his whereabouts. Near a road, Rumplestiltskin and Belle watch Robin Hood heal a sickly woman with the stolen wand. Even though the wand was used for a good purpose as Belle points out, Rumplestiltskin prepares to execute the thief with an arrow. When Belle sees the woman is pregnant, she talks him out of it, as killing Robin Hood will make the child fatherless. Reminded of his own son, he allows the arrow to hit a carriage, scaring the couple into fleeing. Returning to the castle, Rumplestiltskin shows Belle a library, denying that the room is for her, but she understands he did do it for her and there is good in his heart. ("Lacey", "Heart of Gold")
With Rumplestiltskin away in Camelot, he returns to catch Belle examining one of his swords in the castle cabinet. Although he did say that she could look around, this was to test how she would react. Engrossed in his castle collections, Belle reasons she was curious since he never talks about where the items came from. Furthermore, it's her dream to see the world, which is what he gets to do. When she inquiries about Camelot, he chucks her a "souvenir", a magic gauntlet used to locate one's greatest weakness. As he states, the weakness is usually a thing the person loves most. After serving him tea, Belle theorizes he collects things because of having a hole in his heart. Instead, Rumplestiltskin whisks her off to laundry duty. When he goes to check up on Belle, she is gone. From the sky, a raven drops an enchanted sand dollar at him. Inside, he sees an imprisoned Belle who desperately pleas for him to save her by bringing the gauntlet to Demon's Bluff by midnight. Arriving to Demon's Bluff, the Dark One confronts Maleficent by magically strangulating her, and when he asks for her last words, the witch gleefully chokes out that she isn't alone. Rising from the sea, Ursula wraps her tentacles around Belle, and Cruella steps out to pressure him into honoring the ransom. On refusal, Ursula begins crushing Belle's heart, to which Rumplestiltskin throws the gauntlet to Cruella and releases Maleficent. With the terms satisfied, the trio reveal their motivation for having the gauntlet is to know their enemies' weaknesses. As the trio retreat, Ursula pushes Belle and she falls into Rumplestiltskin's arms. When he expresses concern for her safety, a surprised Belle wonders why he cares about her. Stumped by the question, Rumplestiltskin shoves her away from him and snaps that, rather than someone else, only he is allowed to end her life by crushing her heart. Later, he retrieves the gauntlet from the trio. Cruella suggests he join them in their fight to defeat heroes, but Rumplestiltskin boasts that he always wins and doesn't need them to do it. ("Heroes and Villains")
On the night of Baelfire's birthday, Rumplestiltskin sadly lights a candle in his honor. Belle walks in on him and though she apologizes, he coldly orders her out of the room. Instead, she walks up to set a basket of flowers on the table. He gives her a second warning, but she still doesn't leave. Belle notices a shawl sitting nearby and realizes he must have been using the candle in remembrance of someone. She gives her condolences, even asking how old would he be, but Rumplestiltskin states this person is not dead, but lost. He admits it is this person's birthday—without using Baelfire's name—and expresses regrets for his own past actions that tore away their chance of happiness. Belle proposes it's not too late. Though Rumplestiltskin hopes for the same, he thinks his own ending won't be a happy one. ("Going Home")
The Queen, Regina, vents her frustration to Rumplestiltskin about how the citizens of the kingdom don't love her, and they only want her stepdaughter Snow White as Queen. She proposes he teach her a spell to disguise herself so she can fool Snow White and get close enough to kill her. Rumplestiltskin doubts Regina can do it because it took her mother, Cora, a month to learn that spell, and Regina would only be able to change her hair color in a week's time. Regina wants to use any means, so she asks him to cast the spell instead. Because Rumplestiltskin is the one casting the spell, Regina will have no control over when the disguise comes off, and she will be magic less. Another deal is bargained, and in exchange, he wants her to cut off monetary ties with King George of the neighboring kingdom. She wonders why, and Rumplestiltskin retorts he needs the king bankrupt, but it is none of her business. By casting the spell, he turns Regina into a peasant, although to her own eyes, she looks like herself, but to other people, she has a different face. He warns that she won't like what the commoners say about her, though Regina insists it will not matter. Though Rumplestiltskin previously told Regina to call out his name whenever she wants the disguise to come off, he does not respond after she calls twice. When she storms into his castle, he jokingly remarks that she's come to be his maid, though it is a jest she does not find amusing and wants Rumplestiltskin to take off the disguise right this instant. As Regina gazes into the mirror, she is annoyed and ponders if Rumplestiltskin just wants her to admit he was right about what the commoners—that they will never love her. She sadly states it is true, to his absolute glee. He asks what she will do, and she vows to punish them all. Finally, he reverts her back to normal as Regina embraces herself as the Evil Queen. ("The Evil Queen")
Some time later, he is summoned to king's court, where King George begs him to bring his son, who has been killed in a tournament, back from the dead. Rumplestiltskin admits not even magic can bring back the dead, but tells the King that Prince James has a twin who can take his place. In return, he demands the location of King George's family fairy godmother as payment for getting the other twin, which King George reluctantly gives into. Rumplestiltskin goes back to the farm to collect the other twin, David, and convinces him to masquerade as King George's son. ("The Shepherd")
Outside his castle, Rumplestiltskin sights his most hated enemy, Hook, and immediately begins suffocating him until the pirate's companion, Emma, tells him of how he will cast a powerful curse, which she breaks, and and this will reunite him with Baelfire. To keep the past unchanged and ensure the future, Emma and Hook need his help to organize a destined first meeting between Prince Charming and Snow White. After the trio enter his castle, Belle walks in to ask if he needs anything. Strangely, Emma knows Belle, claiming Rumplestiltskin mentioned her, though he did not. Rumplestiltskin shoos his maid away, and then dismisses Emma's claim that he and Belle fall in love with each other. Moving their plan along, Emma and Hook motivate Snow White to steal Prince Charming's ring from King Midas' castle. As they wait for her to succeed, Rumplestiltskin informs them about his possession of a wand that can recreate a portal. When the pair want to sneak into King Midas' castle to check up on Snow White, he provides glamored disguises for them. Back in his own castle, the Dark One discovers the wand can only open a portal by those who traveled through it. He prepares a potion to erase his memories of the future just as the twosome, with another person, arrive back. Rumplestiltskin explains the portal issue and hands the wand to Emma, who cannot wield it, so he traps them in his vault to "protect the future". When Emma does open a portal, Rumplestiltskin demands information about Baelfire's future, to which she reveals his son forgives and loves him, but he dies to save everyone. Shocked, he insists the future can be changed, but Emma warns it'll make things worse. She urges him to drink the potion, which he does after releasing her. Once she disappears into the portal and it closes, Rumplestiltskin, his memories erased, picks up the fallen wand and teleports out of the vault. ("Snow Drifts", "There's No Place Like Home")
One day, Rumplestiltskin catches Belle just before she is heading to town to buy food. He reminds her against trying to run from the castle, especially since her enchanted cloak clasp will let him know if she has, while Belle reassures him she doesn't intend to. On her return, Belle brings home an old friend, Samuel, whose wound she wants to heal. Despite not believing the man can be saved, Rumplestiltskin agrees not to kill him. Later, as Samuel is resting, Rumplestiltskin notifies Belle that he'll be away for a bit. While the Dark One is gone, Samuel admits he is rescuing Belle on her father's orders and intends to capture Rumplestiltskin in Pandora's Box. She, however, refuses to aid him and leads him out of the castle. Soon, Rumplestiltskin returns and conjures the box into his own hands. Belle reveals she learned early on, from a notebook that Samuel carried, that he actually wanted to find the Dark One's dagger and make Rumplestiltskin plunder the Enchanted Forest with it. Not wanting the plan to come into fruition, she had to trick him into leaving. When she asks about her friend's fate, Rumplestiltskin swears he kept his promise not to kill Samuel, without telling Belle he banished him to a swamp. ("Out of the Past")
After Belle has been his maid for several months, he allows her to go into town to fetch him straw for spinning gold. In actuality, he expects to not see her again once she leaves; assuming she will run away. Against Rumplestiltskin's assumptions, as well as her own, Belle returns to the castle to give him true love's kiss; causing him to begin reverting to human form. Shocked by her actions, he mistakenly believes Belle is working with the Queen when she stutters about learning from a woman that kissing him would break his curse. In a fit of anger, Rumplestiltskin locks her in his dungeon and later casts her out of his castle after he claims to value power above everything else. However, Belle challenges Rumplestiltskin, declaring that despite all his efforts to be powerful and feared, he is still a coward at heart for not being able to accept someone could actually love him, in the end power will only give him, "an empty heart and a chipped cup." Some time after Belle has left, the Queen visits Rumplestiltskin and goads him about his ex-maid's torturous fate at the hands of her father, who believed she had been sullied by the Dark One's evil ways, and sought out priests to cleanse her in a locked tower, which ended with her suicide. Visibly shaken by this knowledge, Rumplestiltskin calls the Queen a liar and tells her to leave. Left alone in his grief, he replaces a golden chalice on a pedestal with a teacup Belle had chipped on her first day as his caretaker; the only memento he still has of his lost love. ("Skin Deep")
To find the Fairy Godmother, whose wand he desires, Rumplestiltskin goes to the family manor of a maid named Cinderella. Interrupting the Fairy Godmother's wish granting session, he kills her and takes the wand as a shocked Cinderella watches. He convinces the maid to make a new deal with him instead—she can attend the royal ball, but will owe him something "precious". Cinderella agrees, signs the contract, and hurries off to the ball. ("The Price of Gold")
Some time later, he meets with Snow White, who wants him to give her something to forget the man she loves, Prince Charming. Rumplestiltskin plucks two hairs from her head; using one to create a forgetting potion for her and keeping the other as payment. ("7:15 A.M.")
After Snow White drinks the potion, she only cares about exacting vengeance on the Queen. One of the seven dwarves, Grumpy, drags her to Rumplestiltskin hoping he can fix it, but it's not possible. Instead, he sends Snow White on the road to becoming a murder by giving her Robin Hood's old bow to use on the Queen. On the same day, Prince Charming is ensnared into a deal with Rumplestiltskin in exchange for information on Snow White's whereabouts. Rumplestiltskin takes Prince Charming's cloak as payment, but in truth, he picks off a strand of the man's hair. Entwining the strand with Snow White's hair, he creates the elusive and rare form of true love in a bottle. ("Heart of Darkness")
Rumplestiltskin has further success in creating the Dark Curse and places a single drop of true love on the spell parchment as "a little safety value". Meanwhile, he approaches a struggling Prince Charming in the Infinite Forest, who can't seem to find his way out to reach Snow White. He steals Prince Charming's ring, enchanting it to glow when near Snow White, and suggests another deal. Prince Charming vehemently refuses, and draws his sword. Rumplestiltskin humors him with a fight, but with his powers, he easily defeats Prince Charming, and informs him they're after the same thing—he and Snow White being together. Then, he shows Prince Charming his true love potion. When asked what he knows about true love, Rumplestiltskin describes his own past love as "a brief flicker of light amidst an ocean of darkness", though she died. The fragile nature of true love combined with its unequaled power, the ability to break any curse, is why Rumplestiltskin wants it to be protected. He instructs Prince Charming to hide the potion "inside the belly of a beast". After Prince Charming successfully puts the egg inside the body of a dragon, he surfaces at a beach shoreline near Maleficent's castle. Rumplestiltskin hands over the ring, and then uses his powers to give the latter a princely outfit to match with the occasion. Prince Charming asks why Rumplestiltskin is helping him so much. Mysteriously, the Dark One states he is a fan of true love, and what it creates. ("A Land Without Magic")
Having secured and enacted the deal with Prince Charming, Rumplestiltskin returns to his castle. While spinning gold at his leisure, he is visited by Prince Charming, who wants to bargain in helping a now curse-less Snow White to find the motivation to fight against the Evil Queen for the kingdom. However, Rumplestiltskin has nothing to give him. Instead, Prince Charming comes up with a plan of his own and manages to strengthen Snow White's resolve in battling for the right of the throne. Snow White, having the impression all this was possible because Prince Charming made another deal with Rumplestiltskin, decides she wants to pay the price of magic. In the forest, she summons the Dark One to explain her intention to reimburse him for his services rather than let Prince Charming do so. Rumplestiltskin inquires about the sword Snow White is holding, which she says is the legendary Excalibur of Camelot, and having pulled it out of proves herself to be true claimant to the kingdom. In disbelief, Rumplestiltskin shows her the sword is nothing but a forgery by using magic to dissolve it into dust. After spilling the truth that no deal was made between himself and Prince Charming, he rips a necklace from Snow White's neck as payment for wasting his time. ("Lost Girl")
Soon, a war ensues between Prince Charming and Snow White against the combined armies of the Evil Queen and King George. At long last captured, the Evil Queen is sentenced to death by the kingdom's war council, though Snow White is resentful of the decision. At the execution, Rumplestiltskin and many other citizens gather to watch, but at the last moment, the Evil Queen is allowed to live on Snow White's orders. In the evening, he gives Snow White an enchanted knife to test on an imprisoned Evil Queen to see if she is capable of changing her murderous ways. The Evil Queen fails the test by attempting to stab Snow White with the knife, which is magically rendered ineffective. In addition, whoever uses it will never be able to harm Snow White or Prince Charming in the Enchanted Forest. The Evil Queen, banished to elsewhere, is visited by Rumplestiltskin at a later date. She is deeply upset at never having the chance to kill her enemies again, though Rumplestiltskin stresses a particular caveat of the enchantment--they cannot be harmed in this land, but can in others. His words help her recall the effects of the Dark Curse, and she hurries off to Snow White and Prince Charming's wedding to announce her intentions of using it to destroy their lives for good. ("The Cricket Game")
Since Cinderella's deal with Rumplestiltskin, she captures the attention of Prince Thomas at the royal ball and they soon marry. During the wedding party, Rumplestiltskin shows up just long enough to claim his "precious" price from Cinderella as her firstborn child. Many months later, he meets with Cinderella again, whereupon she tells him she is carrying twins and wants to make a new deal. At first he does not believe her, but after warning Cinderella about the consequences of using magic against him, he eventually signs the contract with a quill filled with squid ink, which paralyzes him. Grumpy and Prince Charming load Rumplestiltskin up into a cart to take him away to prison, but Thomas mysteriously disappears. Upon confrontation, Rumplestiltskin states that Thomas will never return unless he receives her baby. Then, he is carted away to his prison in the dwarves' mine. ("The Price of Gold")
When Snow White becomes heavily pregnant, she also grows even more concerned about the threat of the Dark Curse from her former step-mother. She and Prince Charming go to Rumplestiltskin, the only man powerful enough to counter the Queen's magic. Their escort warns them not to tell him their names, because it will give him power over them, but Rumplestiltskin already knows who they are. Rumplestiltskin agrees to give them information in exchange for their unborn baby's name, to which Snow White agrees, in spite of the guard's earlier warning. He tells the couple that the only thing that can save all the people in the land from the curse is their unborn child who will come back to save them all on her twenty-eighth birthday. As they turn to leave, Rumplestiltskin asks for their child's name. After a moment of hesitation, Snow White states the child's name to be Emma. To help himself to remember this vital piece of information, he repeatedly writes her name on a piece of parchment using squid ink. ("Pilot", "Queen of Hearts")
The Queen tries to fulfill plans to use the Dark Curse, but her first attempt at casting it fails. She visits Rumplestiltskin to find out why, and his price for this information is to receives riches, comfort, and influence in his life once the curse takes effect, and that if he comes to her for any reason, she must give him anything if he uses the word "please". After the Queen agrees to this, Rumplestiltskin tells her that she must sacrifice the heart of the thing she loves most for the curse to work. ("The Thing You Love Most")
On the day the Dark Curse is cast, he expectantly waits for it to take effect. The Queen materializes outside his cage to gloat about her success with the curse and boasts at the knowledge he, like all others will be affected by it, will soon lose their memories of everything. He relishes in asking her how it felt ripping out her father's heart for the curse to work, but she doesn't answer as it is of little importance. Rumplestiltskin can tell despite her triumphant front, she is still unsatisfied with something. He stresses that Prince Charming and Snow White's child will foil her curse, to which the Queen voices plans of getting rid of the baby. Additionally, Rumplestiltskin hints that now she has hole in her heart and will feel the need to fill it in the future. The Queen doesn't take his prophecy seriously, though he shouts she has underestimated the price of magic and will come back for his help someday. Soon after, the curse takes Rumplestiltskin and many other inhabitants of the Enchanted Forest to another land. ("Save Henry", "Pilot")
For events occurring after the casting of the first curse, see Mr. Gold.
Before Second Curse
Rumplestiltskin's body and his dagger are recreated from a black liquid, when his son, Neal, uses a key to open the vault of the Dark One. As an unexpected cost, which Neal is not aware of, he dies while Rumplestiltskin is revived. As his son perishes, Rumplestiltskin grabs hold of him as well as the dagger. However, he is not able to grip both at the same time, and the Wicked Witch snatches the dagger. Unwilling to let Neal perish, he absorbs his son into his own body to keep him alive. Enslaved to the Wicked Witch's orders via the dagger, she orders him to kill Belle. Just before he does, Lumiere entraps the Wicked Witch in flames. Belle flees with Lumiere in tow while Rumplestiltskin is forced to stay behind. ("Quiet Minds")
Imprisoned in a cage in his own castle, Rumplestiltskin busies himself with a spinning wheel. Belle, Prince Charming, Snow White, Robin Hood and Regina break in to ask him how to defeat Zelena, but he responds with gibberish and veiled speech. However, when Belle approaches, he recognizes her and provides information about the banished Good Witch of the South, Glinda, who may be able to help them. His only clue to her whereabouts is a door that can only be entered by the pure of heart. Shortly after, Zelena, discovering Snow White cast another Dark Curse to find Emma, drops a potion into the mixture to erase everyone's memories of the last year in the Enchanted Forest. Before the curse spreads, she drinks a substance to retain her memories, and then passes it to Rumplestiltskin. She gives him the option to remember losing his son, or be foolish enough not to take the potion and forget everything. Left alone, Rumplestiltskin chooses to ingest it; believing that with pain is power, but also vengeance. As he lifts the vial to his lips, Neal breaks free. While Rumplestiltskin is passed out, his son writes a note to Hook asking him to give the potion to Emma, and he then attaches it to a messenger bird. With his last bit of strength gone, Neal returns to his father's body; causing Rumplestiltskin to awaken. ("A Curious Thing")
For events occurring after the casting of the second curse, see Mr. Gold.
During Alternate Reality
After Isaac rewrites everyone's stories in the Heroes and Villains book, Rumplestiltskin becomes a valiant knight known as the Light One, who uses his magic to save villagers from danger. He is married to Belle, and together, they have a young son. However, in this reality, Rumplestiltskin remembers trying to save his previous son, Baelfire, during the Ogre War, only to lose him. One day, he saves Henry from an ogre, before heading off to save another village. ("Operation Mongoose Part 1")
Arriving home, Rumplestiltskin finds Belle has welcomed a stranger, Isaac, into their home. While his wife goes to fetch water from the well, he detects Isaac has other reasons for coming here. Isaac mentions knowing details of Rumplestiltskin's actual life before the alternate timeline, although the Light One remembers none of this, in which he was a coward and abandoned Baelfire. He threatens to reveal all this to everyone and ruin his happiness with Belle unless Rumplestiltskin kills Henry and stops Regina from interrupting Robin Hood's wedding. Stuck in a dilemma, Rumplestiltskin talks to Belle, telling her that the kingdom is in danger and if left unchecked, it will destroy the happiness they have. He worries about making a choice that may be the wrong one, but she is certain he'll do the right thing because he's a hero. Deciding to choose self-preservation, Rumplestiltskin blocks Regina from reaching the wedding, but Emma distracts him with a duel, while the latter rushes for the church. After she is defeated, he bests Henry and prepares to deliver a killing blow, but Regina takes the hit instead. Believing his work is done, Rumplestiltskin teleports away in a glow of light. Once Henry harnesses the quill and becomes the next Author, Isaac's stories are undone and everyone returns to their old lives in Storybrooke. ("Operation Mongoose Part 2")
For events occurring after the reversion of the alternate reality, see Mr. Gold.
Dashed lines denote marriage relationships and relationships that result in offspring
† denotes the deceased
There have been a few hints about Rumpelstiltskin's age on the show. According to Robert Carlyle, Rumplestiltskin is three-hundred years old by the time the Dark Curse is cast. However, the show itself has hinted that Rumplestiltskin is just a couple hundred years old: In "Going Home", his father says, "What are you now? A couple hundred?". In "Family Business", Hook (who knew Rumplestiltskin from before he became the Dark One) refers to himself as approximately two hundred years old.
Rumplestiltskin's voice is inspired by Robert Carlyle's son. According to Robert, his son was wandering though the house making high-pitched voices and sounds. The actor thought this voice would fit Rumpelstiltskin, because there is a child-like quality to the character, and Rumplestiltskin enjoys gleefully tricking people.
According to Adam Horowitz and Edward Kitsis, every time we meet Rumplestiltskin in Fairy Tale Land, he is in a slightly different time period, and therefore Robert actually uses a slightly different voice every single time.
Robert Carlyle revealed in an interview that it takes approximately two hours to dress him in Rumplestiltskin's costume, twenty minutes of which is spent on his boots. He also revealed that it takes about one hour to remove the costume.