Joe Keegan (Pete Schwaba) is the 'Rocky' of stand-up comedy. A fifteen year comedy veteran who was pegged for stardom early on in his career but has blown every major audition he has ever had in legendary fashion. Fresh off a recent fiasco with a heckler that included a broken nose, Joe's friend Kenny (Lance Barber) tells him he can get them an audition for 'The Tonight Show' and that it's 'a can't miss.' The one catch is that it's at a roadside bar in tiny Pine Lake , Wisconsin , hometown of Tonight Show Talent scout, Harvey Skorik who never misses 'Rocktoberfest'. Having doubts but needing a break from L.A. , Joe reluctantly agrees to go.

Arriving in Wisconsin , Joe bombs his first night on stage when local emcee 'Dug' (Thomas Lennon) sabotages him. Joe cannot get a break until he encounter's his former high school English teacher, the beautiful Molly Mahoney (Lauren Holly) who is also at a crossroads in her life, coming off a failed marriage. Molly is excited for Joe's 'Tonight Show' opportunity. Joe tells her he just wants to prove to himself that he hasn't been wasting the last fifteen years of his life. Molly makes him realize just the opposite - that he has been living his dream.

Things finally start looking up for Joe Keegan until he finds that the biggest audition of his life will be in front of his toughest crowd yet; Packer fans, Deer Hunters and The Godfather of Green Bay, Big Jake Norquist (Tony Goldwyn), a former high school football star turned drug dealer who is also in love with Molly.