For his portrayal of Ernest Hemingway in Woody Allen's Midnight in Paris (2011) he was nominated for the Independent Spirit Award for Best Supporting Male.

[5] Stoll made his Broadway debut as a member of the ensemble in the 2003 revival of William Shakespeare's Henry IV at the Vivian Beaumont Theatre.

Stoll portrayed Marco in the 2010 Broadway revival of the Arthur Miller play A View from the Bridge acting opposite Liev Schreiber and Scarlett Johansson.

He played Ernest Hemingway in Woody Allen's romantic comedy film Midnight in Paris (2011) for which he earned acclaim as well as a nomination for the Independent Spirit Award for Best Supporting Male.

[8] In 2014, Stoll also played Austin Reilly, an NYPD police officer, in the action film Non-Stop, and Paul Altman in the comedy-drama This Is Where I Leave You.

Also in the summer of 2016, he played the wily Greek warrior Ulysses in the Public Theater production of Troilus and Cressida by William Shakespeare, in Central Park.

[13] In 2023 he returned to Broadway in the Branden Jacobs-Jenkins play Appropriate acting opposite Sarah Paulson, Natalie Gold and Elle Fanning.