Todd Louiso, John Cusack, and Jack Black in High FidelityHIGH FIDELITY

John Cusack, at his best, has made a career out of playing two disarmingly similar character types: those who feel like losers, but are actually cooler than anyone else in the room (see his roles in The Sure Thing, Say Anything..., and Grosse Pointe Blank), and those who think they're cooler than anyone else in the room, but are actually losers (The Grifters, Bullets Over Broadway, and Being John Malkovich).