5. JENNA JAMESON

Music Video: "Without Me" (2002)
In "Without Me," Eminem's superhero counterpart Rap Boy (in Robin's costume) puts Bruce Wayne to shame. Before suiting up to answer the call of duty, Em wakes up in bed with quintessential porn queen Jenna Jameson. Given the entire video was a compilation of timely pop culture parodies, Jameson's pointedly self-aware cameo was definitely warranted and quite the pleasant surprise.