The movie: American Reunion (2012)
The player(s): Seann William Scott

In the first film in the American Pie franchise, released in 1999, Steve Sifler's (Scott) immaturity can be chalked up to the fact that he is indeed playing an 18-year-old. But in later installments, including 2003's American Wedding and 2012's American Reunion, he's still got the ability to land the ladies, despite his continued high school-like antics. In the latest edition, he even manages to bed his buddy Finch's MILF, played by Rebecca De Mornay.