20. Robin Williams in Bobby McFerrin's "Don’t Worry, Be Happy"
The video's fine, but we really just wanted to get this earworm stuck in your head again. You're welcome.
19. Liv Tyler and Alicia Silverstone in Aerosmith's "Crazy"
With "Amazing" and "Livin' on the Edge," Alicia Silverstone was already Aerosmith's go-to actress for wild child, "Screw you, Dad" roles. When she was partnered with frontman Steven Tyler's daughter Liv (in her on-screen debut), MTV couldn't play this video enough. The video features what teenage girls normally do for fun middle-aged men assume teenage girls do for fun e.g., engaging in pillow fights, participating in amateur stripper nights and seducing farmboys.
18. Dennis Hopper and Dean Stockwell in Gnarls Barkley's "Smiley Faces"
Playing off the "Who is Gnarls Barkley?" marketing campaign, Dennis Hopper and Dean Stockwell play a music historian and A&R man, respectively, delving mockumentary-style into the origins of the mythical Gnarls figure. Turns out they were swinging with Duke Ellington, jamming at Woodstock and hanging with Warhol and Lou Reed. This video is basically a hipster's "Forrest Gump."
17. Eddie Murphy in Michael Jackson's "Remember the Time"
Four years after playing Prince Akeem in "Coming to America," Eddie Murphy takes on the role of another African ruler in this John Singleton-directed video centered around ancient Egypt. With cameos by Iman, Magic Johnson and The Pharcyde (briefly seen as a dancing group), the video's special effects were groundbreaking for its time and is closer in style and length to a short film than a conventional music video. Best line: Magic after seeing someone beheaded for not entertaining the Queen: "That's cold."
16. Kim Basinger in Tom Petty's "Last Dance With Mary Jane"
It may not be the apex of human civilization, but every guy has had the "Would you have sex with [famous actress or model]? What if she was dead?" conversation with his peers. This kind of talk usually ends around the age of 13, but some guys keep it going well past the appropriate time. This video's the PG-rated visual representation of that conversation.
15. Christina Hendricks in Broken Bells' "The Ghost Inside"
Is there anything more soul-crushing than giving both legs and a hand for a shot at fame, only to discover that your best place for success is actually a desolate, barren wasteland? Broken Bells likes metaphors.
14. Danny Aiello in Madonna's "Papa Don't Preach"
Danny Aiello has always been the go-to actor when you need a working-class, exasperated middle-aged man? In fact, we're pretty sure he was born 40 years old, but that's a different article. Yes, it was the 1980s, but you still have to question Madonna's choice of baby daddy; we know mullets and sleeveless tees were the look back then, but you know that guy is still rocking that outfit 30 years later.
13. Kristen Bell in Yeasayer's "Madder Red"
Who would have thought some weird, veiny one-armed bulbous creature would inspire such pathos? What could have been simply a weird love affair between Kristen Bell and her ball-shaped lover turns into a sad tale of lost love and remorse. Though we're still wondering if that thing went to a regular hospital or animal clinic.
12. Michael Cera in Islands' "No You Don't"
"Don't buy dope from the man you don't know," sings Islands frontman Nicholas Thorburn in this "High School Academic Anti-Drug Supplementary" video. So begins Michael Cera's drug trip into psychedelic worlds and purposefully cheesy 1980s graphics. We're still not sure if doing acid with the actor would be the most or least pleasurable drug experience ever. Discuss.
11. Keanu Reeves in Paula Abdul's "Rush Rush"
Taking its cue from Nicolas Ray's "Rebel Without a Cause," this really needs to be remade today with James Franco and, just for fun, an aging Paula Abdul still portraying a high school student. Among a myriad of bizarre shots, we're most enthralled by the incongruous opening shot of Keanu imitating a cymbal-clapping toy. Avant-garde cinema of the highest order.