He has also acted or voice-acted in films such as I Love You, Man (2009), Get Him to the Greek (2010), Adult Beginners (2014), Vacation (2015), Sausage Party (2016), The House (2017), The Secret Life of Pets 2 (2019), How It Ends (2021), The Bob's Burgers Movie (2022), First Time Female Director (2023) and Red One (2024).

[10] Early in his career, Kroll contributed writing for Comedy Central's Chappelle's Show and MTV's Human Giant.

[12] He has studied and performed regularly at the Upright Citizens Brigade Theater in NYC and LA and co-hosted the stand-up show Welcome to Our Week with Jessi Klein.

[13][14] He is well known as a performer for his characters such as Bobby Bottleservice, who has been featured in a number of online videos for the Funny or Die website, including the Ed Hardy Boyz and an audition tape for the MTV show Jersey Shore.

[18] Kroll's first significant career success came when he co-starred in the ABC sitcom Cavemen, based on the Geico insurance TV-commercial characters.

He made appearances on numerous Comedy Central series such as Reno 911!,[20] John Oliver's New York Stand Up Show, and The Benson Interruption, both performing as himself and in character.

[citation needed] Kroll had a starring role as Rodney Ruxin in the FXX comedy series The League, which aired October 29, 2009 to December 9, 2015.

Kroll starred in A Good Old Fashioned Orgy and had supporting roles in comedy films such as Sing, Dinner for Schmucks, Date Night, Get Him to the Greek, Adventures of Power, and I Love You Man.

Seitz further stated that "[t]he way Kroll savors every syllable of his alternately peevish, self-pitying and nonsensical dialogue—aided mightily by the animators, who've given the character a fireplug body and a waddling walk—transforms the ridiculous into the sublime.

"[32] In recent years, Kroll has taken several non-comedic acting roles, such as that of Bernie Cohen in Loving and Rafi Eitan in Operation Finale, both historical drama films.