From his breakout days as the Upper East Side’s favorite bad boy to carrying major Marvel blockbusters and delivering award-winning, transformative performances in indie cinema, Stan has quietly built one of the most versatile filmographies in modern Hollywood. Whether he is playing complex anti-heroes, real-life figures, or terrifying thrillers, he brings a magnetic intensity and deep empathy to every frame.
To celebrate his 44th milestone, here is a retrospective look at Sebastian Stan’s 10 most outstanding and defining roles.
1. James Buchanan “Bucky” Barnes / The Winter Soldier – Marvel Cinematic Universe
- Where to Watch: Disney+
No role has defined Stan’s global popularity more than Bucky Barnes. First introduced as Steve Rogers’ loyal best friend in 2011’s Captain America: The First Avenger, Stan evolved the character into the terrifying, brainwashed assassin in 2014’s The Winter Soldier—a film widely regarded as one of the peak chapters of the entire MCU. Stan brought tragic depth, lethal physical presence, and heartbreaking vulnerability to a soldier fighting to reclaim his humanity.
2. Edward / Guy – A Different Man (2024)
- Where to Watch: Max / VOD
In one of the most critically praised performances of his career, Stan starred in Aaron Schimberg’s dark psychodrama A Different Man. Playing an aspiring actor with neurofibromatosis who undergoes a radical medical procedure to transform his appearance, Stan delivered an astonishing, deeply vulnerable exploration of identity, insecurity, and self-worth. His performance earned him the prestigious Silver Bear for Best Leading Performance at the Berlin International Film Festival.
3. Donald Trump – The Apprentice (2024)
- Where to Watch: VOD
Directed by Ali Abbasi, this biographical drama captures the formative early years of Donald Trump as a rising real-estate developer in 1970s and 80s New York under the tutelage of ruthless lawyer Roy Cohn (Jeremy Strong). Rather than relying on simple impressionism, Stan delivered a grounded, nuanced, and chillingly precise physical and vocal transformation that earned him widespread acclaim during awards season.
4. Tommy Lee – Pam & Tommy (2022)
- Where to Watch: Hulu
Sinking his teeth into one of the wildest biographical series in recent memory, Stan underwent extensive physical training and prosthetic work to embody Mötley Crüe drummer Tommy Lee. Opposite Lily James’s Pamela Anderson, Stan captured Lee’s chaotic, rock-and-roll energy while grounding the series’ narrative in empathy. His performance netted him his first Primetime Emmy and Golden Globe nominations.
5. Steve / Brandon – Fresh (2022)
- Where to Watch: Hulu
In Mimi Cave’s darkly hilarious and grotesque romantic thriller, Stan displayed his terrifying ability to play a charm-infused monster. Playing “Steve,” a seemingly perfect man who woos Daisy Edgar-Jones’s character only to reveal an appetizingly horrifying secret lifestyle, Stan danced through the film with unhinged charismatic glee, proving once again that he excels when playing edgy, unpredictable characters.
6. Jeff Gillooly – I, Tonya (2017)
- Where to Watch: Hulu / VOD
In Craig Gillespie’s Oscar-winning satirical biopic, Stan starred opposite Margot Robbie as Jeff Gillooly, the infamous, mustache-toting, abusive ex-husband of figure skater Tonya Harding. Stan struck a delicate balance, portraying Gillooly as a bumbling, deeply delusional schemer without ever downplaying the violent reality of the abusive relationship.
7. Prince Jack Benjamin – Kings (2009)
- Where to Watch: VOD
Before becoming a household name, Stan starred in NBC’s ahead-of-its-time, high-concept political drama Kings. Playing a closeted, tortured royal heir struggling against his tyrannical father (Ian McShane) in a modern-day absolute monarchy, Stan delivered a magnetic, emotionally complex performance that signaled the major dramatic actor he was destined to become.
8. Carter Baizen – Gossip Girl (2007–2010)
- Where to Watch: Max
For an entire generation of television viewers, Stan’s grand entrance into pop culture came as Carter Baizen, the suave, wealthy rogue who repeatedly drifted into Manhattan to cause chaotic romantic drama for Serena van der Woodsen and Blair Waldorf. Though his appearance was recurring, Stan’s scene-stealing arrogance and effortless charm made Carter an instant fan favorite.
9. Dr. Chris Beck – The Martian (2015)
- Where to Watch: Fubo / VOD
Joining an all-star ensemble cast led by Matt Damon in Ridley Scott’s Academy Award-nominated sci-fi blockbuster, Stan played Dr. Chris Beck, the Ares III flight surgeon and astronaut. Stan brought warm sincerity, intelligence, and quiet heroic resolve to the crew as they risked everything to return to Mars and rescue their lost teammate.
10. Jefferson / The Mad Hatter – Once Upon a Time (2012)
- Where to Watch: Disney+
In ABC’s hit fantasy series, Stan brought heartbreaking pathos to Jefferson, a portal-jumping hatmaker trapped between dimensions and separated from his daughter. Blending whimsical madness with grief and desperation, Stan turned a guest-starring arc into one of the most memorable character storylines in the show’s early seasons
