18. Eminem "My Name Is" (1999)
Director: Philip Atwell
It opens on an everyday, white trash, presumably suburban living room, with a couple watching shitty TV. And then: The Slim Shady Show-a twisted take on Leave It To Beaver-comes on, drawing their attention (and ire). And then Eminem proceeds to literalize most of the lines in the song, going through, count 'em, fifteen different setups and/or costumes, which include Marilyn Manson and then-president Bill Clinton emerging from behind a podium pulling up his pants, with a Monica Lewinsky lookalike following in his wake. It was a brilliant clip, aimed squarely at the attention spans of an attention-span lacking generation, that was equal parts stunningly current, shocking, weird, and hilarious (especially Dr. Dre playing a doctor, calling his rapper a "basehead" on MTV). Parody needs to work really hard to become iconic; director Phillip Atwell and Eminem somehow pulled it off, and as dated as the clip is in 2013, it's still a blast to watch today.