23. Dr. Dre f/ Snoop Doggy Dogg "Dre Day" (1993)

Director: Dr. Dre

Oh, man. It's a classic clip, but it's also one that gets harder to watch over the years. The video, which featured a character Dre dubbed "Sleazy-E" getting a record deal from an evil sleazeball exec (played by none other than Interscope marketing honcho Steve Berman). Sleazy-E's adventures are intercut, of course, with Dre and Snoop having a banging part. And by the end of the video, Sleazy-E's been shot and is homeless and hungry, holding up a sign by a freeway: "WILL RAP FOR FOOD." Shortly after that, a title card on black: "This video is a work in [sic] fiction. The characters, incidents & plot are a product of the creative imagination of the artist. Any resemblance to any persons, living or dead, is entirely coincidental." Except: like hell it was. Eazy-E and Dre's fued continued to play out in public (and in the video space) again in the "Real Muthaphuckkin G's," but Dre's clip dropped first, and dropped stronger. Eazy-E would make amends with Dre and Snoop shortly before he died two years later, but-despite being a great video, and a great song-it's still a reminder of the kind of creative brilliant could've-been output that beef so often kills.