Elton John had a huge hit duetting with Kiki Dee on "Don't Go Breaking My Heart," but he's also performed it with RuPaul and Miss Piggy.

Salt's "mighty good man" in the Salt-N-Pepa "Whatta Man" video is played by Tupac Shakur.

David Bowie's "Ziggy Stardust" was likely based on various musicians in his ambit, including Iggy Pop (zIGGY), and Jimi Hendrix, who played guitar left-handed ("He played it left hand").

You wouldn't know it from the upbeat melody, but "Walkin' On The Sun" by Smash Mouth is about the 1992 Los Angeles Riots.

Joni Mitchell's "Big Yellow Taxi" is about the commercialization of Hawaii. On her first trip to the islands, she looked out of her hotel window and saw a parking lot as far as the eye could see.

"You Get What You Give" by The New Radicals was the first hit song to use the word "frenemies" in the lyrics.
Billy Joel and Hall & Oates hated making videos, so they chose a director with similar contempt for the medium. That was Jay Dubin, and he has a lot to say on the subject.
Tom stopped performing Thompson Twins songs in 1987, in part because of their personal nature: "Hold Me Now" came after an argument with his bandmate/girlfriend Alannah Currie.
Kooper produced Lynyrd Skynyrd, played with Dylan and the Stones, and formed BS&T.
When singers started spoofing their own songs on Sesame Street, the results were both educational and hilarious - here are the best of them.
For songwriters, Johnny represents the American man. He has been angry, cool, magic, a rebel and, of course, marching home.
Chad tells tales from his time as drummer for Nirvana, and talks about his group Before Cars.