For his portrayal of a young Donald Trump in The Apprentice (2024), Stan earned Best Actor nominations at the Golden Globes, BAFTAs and Academy Awards.

[9] During Stan's years at the Rockland school, he starred in productions including Harvey, Cyrano de Bergerac, Little Shop of Horrors, Over Here!, and West Side Story.

He attended Rutgers University's Mason Gross School of the Arts, which enabled him to spend a year abroad studying acting at Shakespeare's Globe Theatre in London, England.

This was followed by several film appearances, including Tony n' Tina's Wedding, The Architect, and The Covenant (both 2006), followed by a recurring role on Gossip Girl as Carter Baizen, beginning in 2007.

In 2010, he appeared in Darren Aronofsky's ballet thriller Black Swan and played the role of antagonist Blaine in the comedy Hot Tub Time Machine.

[14] In 2012, Stan starred in the thriller Gone and the supernatural horror film The Apparition; he also began a recurring role in the TV series Once Upon a Time as the Mad Hatter.

[17] The same year, he also appeared in the USA Network miniseries Political Animals as the troubled gay son of a former First Lady,[18] which earned him a nomination for the Critics' Choice Television Award for Best Supporting Actor in a Movie/Miniseries.

[30] In February 2019, he replaced his MCU co-star Chris Evans in the southern gothic crime drama film The Devil All the Time, which premiered on Netflix in 2020.

[36] Lucy Mangan of The Guardian described their performances as "astonishing" adding, "They each achieve the feat of uncannily resembling – aesthetically, vocally, and in every mannerism – the real-life people, without descending into mimicry.

[38] Sophie Butcher of Empire praised their chemistry adding, "Stan in particular is having a ball, unleashing the kind of unhinged energy we’ve seen most recently from him in Pam & Tommy".

[44] Since his appearance in the television series Gossip Girl in the role of Carter Baizen, the actor was in a relationship with the leading actress Leighton Meester until April 2010.

[45] After a joint photo at fellow actor Robert Pattinson's birthday party in May 2022, Stan and British actress Annabelle Wallis made their relationship public from December 2022.

[46] Stan is a supporter of many charitable organizations, including Our Big Day Out, a nonprofit based in Romania that helps provide children with a higher quality of life.