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Chevy Chase in Paul Simon’s “You Can Call Me Al” (1986)
The first single off of Paul Simon’s seminal Graceland album featured Chevy Chase in a starring role. Mockingly lip syncing the singer until the two are dancing in unison at the end, the MTV staple was conceived in part by Saturday Night Live executive producer Lorne Michaels.
George Lucas directed this video for Paula Abdul’s No. 1 hit, tipping its hat to the classic film Rebel Without a Cause with Keanu Reeves in the James Dean role.
Alicia Silverstone in Aerosmith’s “Cryin’” (1993)
This late-era Aerosmith video set the gold standard for celebrity cameos. Not only did it kick-start Alicia Silverstone’s career (two years later, she would land the lead in Clueless), but it also promoted a repeat performance in the band’s clip for “Crazy.” And a video star was born. Fun fact: a young Josh Holloway (Lost) also makes an appearance in “Cryin’” as Silverstone’s purse-snatcher.
Katherine Heigl in Josh Kelley’s “Only You” (2005)
First comes video, then comes marriage… In a true story that could only happen in Hollywood, singer-singwriter Josh Kelley picks a little known Katherine Heigl to star in the clip for his song “Only You,” the two actually fall in love and get married two years later.
Zach Galifianakis in Fiona Apple’s “Not About Love” (2006)
Zach Galifianakis proves he has a knack for lip-synching in this Fiona Apple clip, which finds him sharing a bed with the elusive singer.
Scarlett Johansson in Justin Timberlake’s “What Goes Around… Comes Around” (2007)
Megan Fox in Eminem’s “Love the Way You Lie” (2010)
In one of 2010’s most disturbing and violent videos, Megan Fox plays a beaten woman as Rihanna, a real-life domestic abuse survivor, delivers the powerful chorus to complement Eminem’s rage-filled rhymes: “Just gonna stand there and watch me burn/ Well that’s all right because I like the way it hurts.”
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