The Winner (2007)

S1E4 What Happens in Albany, Stays in Albany

Since Alison is unable to accompany Josh to Albany for the State Spelling Bee, she asks Glen to step in as his chaperone. Realizing that nobody at the event knows them, they come up with a plan to create new identities to impress the girls. Glen transforms into the suave airline pilot "Lance Manley" by sporting a toupee, while Josh plays the role of an arrogant spelling champion.