Sebastian Stanrose to fame playing Bucky Barnes in the Marvel Cinematic Universe, but at the beginning of his MCU run, he played another tragic character in an underrated fantasy TV show. Sebastian Stan was no newcomer when he joined the MCU, but the Winter Soldier/Bucky Barnes was the character that boosted his career.Stan’s acting careerbegan in 2003, with a one-episode appearance inLaw & Order. The following year, Stan had a minor role inTony n’ Tina’s Wedding, after which he continued his career on the big screen.

After his role as Chase Collins in the dark fantasy movieThe Covenant(alongside Chace Crawford), Stan returned to TV inGossip Girl, where he played Carter Baizen, followed by the drama TV seriesKings. After roles in movies likeHot Tub Time MachineandBlack Swan, Stan was cast as Steve Rogers’ (Chris Evans) best friend, Bucky Barnes, inCaptain America: The First Avenger. Meanwhile, Stan returned to TV one more time, now in the fantasy seriesOnce Upon a Time, where he played one of the show’s most tragic characters.

Sebastian Stan as Jefferson looking upset in Once Upon A Time

Once Upon A Time Ran For Seven Seasons

Created by Edward Kitsis and Adam Horowitz,Once Upon a Timepremiered on ABC in 2011.Once Upon a Timegave a twist to fairy tales and their most famous characters, taking the audience to the fictional town of Storybrooke in Maine. There, 10-year-old Henry Mills (Jared S. Gilmore) realizes thatthe residents of Storybrooke are fairy-tale characters who were transported to the real worldand had their memories wiped.

In Storybrooke, the characters live an unchanged existence, unaware that they don’t age and of their past lives.

Once Upon a Time Jefferson and Grace

The one behind this is the Evil Queen (Lana Parrilla), who in the real world goes by Regina and is the town’s mayor. With the help of Rumplestiltskin (Robert Carlyle), the Evil Queen sent everyone to Storybrooke in revenge against Snow White (Ginnifer Goodwin) and her allies. In Storybrooke, the characters live an unchanged existence, unaware that they don’t age and of their past lives. Henry is Regina’s adoptive son, and he discovers that his biological mother, Emma (Jennifer Morrison), is Snow White and Prince Charming’s (Josh Dallas) daughter.

Among Storybrooke’s residents was Jefferson (Stan), who in his past life was the Mad Hatter.

Once Upon a Time Poster

Henry also discovers that Emma was sent to the real world to protect her from the Evil Queen and thus was transported before the curse was cast. As such, Emma is the one who will save them all and break the curse, and so Henry brings her to Storybrooke. The format ofOnce Upon a Time’s episodes was one segment exploring the characters’ lives before the curse and the other following them in the real world. Among Storybrooke’s residents was Jefferson (Stan), who in his past life was the Mad Hatter, but his story was far from funny and colorful.

Jefferson’s story inOnce Upon a Timewas tragic before and after the spell was cast, and to make it worse, he retained his memories after he arrived in the real world. In his past life,Jefferson was a thief who could travel between worlds through a portal hat. During one of his assignments, Jefferson met fellow thief Priscilla, with whom he fell in love and had a daughter, Grace. Years later, as they faced financial trouble, Jefferson tried to steal the Clock of Evermore from the Match Hare, who rewound time with the clock and forced Jefferson to stay for a never-ending tea party.

Priscilla rescued Jefferson but was fatally injured in the process, and with her last breath, she encouraged Jefferson to return home to their daughter. After that, Jefferson stopped using the hat and chose to make a living as a mushroom seller as long as he could be with Grace. Some time later, the Queen asked for his help retrieving something from another land, and after initially turning it down, Jefferson reluctantly agreed as he realized he couldn’t give Grace the life she deserved. Jefferson warned the Queen that if two people entered Wonderland, only the same number of people could exit.

The Queen of Hearts ordered him to make another hat, but Jefferson could never replicate it, and this drove him mad.

The Queen wanted to go to Wonderland to rescue her father, and so she left Jefferson trapped in Wonderland. Jefferson was then captured by the Queen of Hearts, who, after learning about his portal hat, ordered him to make another one, but Jefferson could never replicate it. This drove him mad, thus becoming the Mad Hatter. In Storybrooke,Jefferson was tortured by his past memories and his new reality, where Grace was his neighbor’s daughter and had no recollection of their past life together, and, to make it worse, he was once again betrayed by Regina.

Jefferson’s story came to an end inOnce Upon a Timeseason 2, after the curse was broken, but instead of the characters being sent back to fairy-tale land, they stayed in the real world but remembered who they all were. Despite this, Jefferson didn’t reunite with Grace right away, and it wasn’t until Henry persuaded him to do it that Jefferson overcame his guilt about traveling to Wonderland years before and reunited with Grace.

The Mad Hatter fromAlice in Wonderlandis not a tragic or dark character, butOnce Upon a Timecleverly gave him that twist to add substance to the character and build a backstory for him. Jefferson suffered in fairy-tale land and lost his family thanks to Regina, only to be betrayed by her again in the real world. Luckily,Once Upon a Timegave Jefferson the happy ending he deserved, but he never appeared in the show again after his reunion with Grace.