Flynn had a minor role in "Mean Girls" as the father of Lindsay Lohan's character. He then played the part of an anonymous police officer in '; this scene was cut out of the final version of the film, though it can be viewed in the straight-to-DVD spin-off film ', and in the deleted scenes of the "Anchorman" DVD. He had a minor role in "Major League" as a longshoreman and fan of the Cleveland Indians. Flynn had a role on Phil Hendrie's animated pilot that was not picked up by FOX. He was also the first baseman in the movie "Rookie of the Year".