My favorite comedy of all time and to me, next to Anchorman, the most quotable film of all time. This movie established my love for Steve Carrell and made me realize he can perform such vastly different roles to perfection. The whole cast of this film eventually got famous for their comedic genius. There’s not a single dull moment in this amazing rom-com film about a guy trying to lose his virginity at 40 with a little help from his friends.