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He began performing at Comedy Sportz (now called Comedy City) in Kansas City, Missouri. Sudeikis was later cast in The Second City Touring Company and performed greatest hit shows while on the road.He moved to Chicago, Illinois, where he studied at the Annoyance Theatre and IO Theater (formerly known as Improv Olympic) and was one of the founding members of the long form team, J. In the early 2000s, he became a founding member of The Second City Las Vegas, where he performed at the Flamingo.In May 2010, Sudeikis joined the cast of the Seth Gordon comedy film Horrible Bosses (2011), which also starred Jamie Foxx, Kevin Spacey, Jennifer Aniston, Colin Farrell, Charlie Day, and Jason Bateman.
After previously being credited as a recurring guest in season one, Sudeikis was bumped up to a series regular beginning in season two.In 2017, Sudeikis executive produced for comedy television series, Detroiters. Sudeikis starred in the Netflix film, Kodachrome (2017), alongside Ed Harris and Elizabeth Olsen.He made appearances as Glenn in Permission (2017) and as Dave Johnson in Downsizing (2017).He reprised his role of Kurt Buckman in Horrible Bosses 2 (2014).
Sudeikis starred as Jake in the romantic-comedy film, Sleeping with Other People (2015), alongside Alison Brie.He began his film career with supporting roles in Watching the Detectives (2007), The Ten (2007), Meet Bill (2007), What Happens in Vegas (2008) and The Rocker (2008).