Bradley Cooper auditioned for the role that eventually went to Seth Myers
There is a fight scene where Todd Stone movie-punches Jake Barrymore and makes the punching sound effect with his mouth, not knowing that the sound effects are made in the editing process. During the actual fight scene between Sam's friend, Jake, Larry, and Martin, the sound effects of the blows are delayed about 7 seconds, a play on Todd's confusion about the sound effects.
The blue shirt Jake Barrymore is wearing in the confession speech scene is identical to the red one Seth Meyers' brother, Josh Meyers, wore in the 'That 70's Show' episode 'Misfire'.