Billy Joel's "Uptown Girl" is about Christie Brinkley, who he married, but it started as a song about Elle McPherson, who he also went out with.
"Come Dancing" by The Kinks was inspired by the older sister of Ray Davies, who would make guys take her out dancing and spend their money on her, only to send them home frustrated with just a peck on the cheek.
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").
Props to Aretha Franklin: her song "Respect" introduced the term "propers" as a sign of proper respect.
"Mrs Robinson" was originally called "Mrs Roosevelt," most likely after First Lady Eleanor Roosevelt. It became "Mrs Robinson" when it was considered for use in the film The Graduate.
Don't play "I Will Always Love You" at your wedding - Dolly Parton wrote it about leaving someone behind to strike out on her own.
Jon Anderson breaks down the Yes classic "Seen All Good People" and talks about his 1000 Hands album, which features Chick Corea, Rick Derringer, Ian Anderson, and many other luminaries.
You know the scenes - Tom Cruise in his own pants-off dance off, Molly Ringwald celebrating her birthday - but do you remember what song is playing?
Did Eric Clapton really write "Cocaine" while on cocaine? This question and more in the Clapton edition of Fact or Fiction.
These Three famous songs actually describe how they were written - late into the evening.
The lead singer/lyricist for Anberlin breaks down "Impossible" and covers some tracks from their 2012 album Vital.