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His character work features prominently in Kroll Show.

Kroll was honored with the Breakout Star of the Year award from the 2013 Just For Laughs Comedy Festival in Montreal, Canada.

Valley Girl is a 1983 American romantic comedy film directed by Martha Coolidge, and stars Nicolas Cage, Deborah Foreman, Michelle Meyrink, Elizabeth Daily, Cameron Dye and Michael Bowen.

The American release of Valley Girl was April 29, 1983.

His voice work includes the character Stu on the HBO animated series The Life & Times of Tim, as well as Andrew Le Gustambos, the flamboyant, bisexual drama teacher in the animated Fox comedy series Sit Down, Shut Up. Kroll starred in A Good Old Fashioned Orgy and had supporting roles in comedy films such as Sausage Party, Dinner For Schmucks, Date Night, Get Him to the Greek, Adventures of Power, and I Love You Man.

In 2017, Kroll had a voice role as villainous mad scientist Professor Poopypants in the Dream Works animated superhero film Captain Underpants: The First Epic Movie.

Concurrently, he created and starred in his own Comedy Central sketch series, Kroll Show, which aired January 16, 2013 to March 24, 2015.

Kroll has a recurring role on Childrens Hospital on Adult Swim. Kroll was one of the roasters on the Comedy Central Roast of James Franco.

He is well known as a performer for his characters: Bobby Bottleservice, Fabrice Fabrice, and Gil Faizon of The Oh, Hello Show, which he created with writing partner John Mulaney.Despite this, Julie reconciles with Tommy and later dumps Randy.A heartbroken Randy gets severely drunk, makes out with his ex-girlfriend (Tina Theberge), and nearly gets into a fight with a gang of low riders before Fred saves him.Later that day at the beach, Julie trades shy glances with a young man in the distance.That night, at a party at Suzi's house, Julie locks eyes with Randy (Cage), a Hollywood punk who has crashed the party with his friend, Fred (Dye).