YEAR: 1999
40 has a pretty big role in Sofia Coppola's critically-acclaimed 1970s period piece, playing one of the neighborhood kids who is obsessed with the pretty blonde Lisbon sisters. In this scene, 40, Josh Hartnett, and a crew of guys arrive to take the sheltered girls to the homecoming dance, with 40 behind the wheel in his dad's Cadillac. He might seem timid, but 40 ends up getting it in later, making out with his date while drinking peach schnapps under the bleachers. (Watch the clip til the end to see 40 reveal his mafia credibility. G shit!)