Koechner first became involved in performing when he began studying improvisational comedy in Chicago at ImprovOlympic, under the teachings of Del Close, before joining the Second City Northwest. After year long stints of doing sketch comedy on Saturday Night Live and Late Night with Conan O'Brien in the mid 1990s, Koechner began appearing with small roles in the films such as Wag the Dog, Austin Powers: The Spy Who Shagged Me, and Man on the Moon.
While filming the country mockumentary film Dill Scallion in 1998, Koechner befriended actor/comedian Dave 'Gruber' Allen, and eventually began performing as the comedy duo, The Naked Trucker & T-Bones Show, a live musical comedy act. The act became a hit at Hollywood clubs such as Largo, and Allen and Koechner were invited to open for Tenacious D. In 2007, Koechner and Allen created and starred together in a Naked Trucker & T-Bones Show sketch comedy series that ran for one season on Comedy Central.
After his breakout role as Champ Kind in the 2004 comedy Anchorman, Koechner began appearing frequently with larger supporting roles in many high-profile comedic films including Talladega Nights, Thank You for Smoking, Waiting..., Semi-Pro, The Goods: Live Hard, Sell Hard, and Extract. His first leading film role, as Coach Lambeau Fields in Fox Atomic's sports comedy, The Comebacks opened on October 19, 2007. Koechner most recently reprised his role of Champ Kind for Anchorman 2: The Legend Continues and is receiving praise for his dark turn in the 2014 black comedy Cheap Thrills.
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