11. Jake Gyllenhaal - City Slickers
Castle Rock EntertainmentPerhaps this is slightly unfair, but considered the success Jake Gyllenhaal has had since this film, we think he'll contain his embarrassment. City Slickers is a 1991 classic, really only notable as it is the first onscreen appearance of young Jake Gyllenhaal, and although it's no Jarheads - he comports himself admirably. Thin on plot and reasons to watch, Jake Gyllenhaal stars (although briefly) alongside Billy Crystal; pulling faces and generally acting as the ten year old child he was at the time. Still, everybody has to start somewhere, and what better place than being guided through a hollywood film by Billy Crystal?