The title track of Madonna's third album was about her then-husband, actor Sean Penn. The two divorced in 1989, although Madge said she felt he was still "the love of her life" in the 1991 documentary Truth or Dare.
Taylor Swift's "Dear John"
Taylor Swift's "Dear John"
A) John Kerry
B) John Mayer
C) Lil Jon
D) John Wayne Gacy
Answer: B) John Mayer
Although Swift never explicitly acknowledged her 2010 Speak Now track was about Mayer treating her body like less than a wonderland, Mayer certainly took it that way. "It really humiliated me at a time when I'd already been dressed down," he told Rolling Stone.
No Doubt's "Don't Speak"
No Doubt's "Don't Speak"
A) Gavin DeGraw
B) Tom Dumont
C) Tony Kanal
D) Gavin Rossdale
Answer: C) Tony Kanal
Gwen Stefani wrote No Doubt's 1996 hit about her bandmate and former boyfriend Tony Kanal, who she dated for seven years. Stefani met her current husband, Bush frontman Gavin Rossdale, in 1995.
Crosby, Stills, Nash & Young's "Our House"
Crosby, Stills, Nash & Young's "Our House"
A) Marianne Faithfull
B) Janis Joplin
C) Joni Mitchell
D) Grace Slick
Answer: C) Joni Mitchell
Graham Nash wrote the Déjà Vu album track about his brief fling with singer-songwriter Joni Mitchell in less than an hour. On the same album, the group covered her song "Woodstock."
Katy Perry's "Circle the Drain"
Katy Perry's "Circle the Drain"
A) Russell Brand
B) Joe Jonas
C) John Mayer
D) Travie McCoy
Answer: D) Travie McCoy
"This song was an anvil I had to get off my chest," Perry once said. Although she never directly names the Gym Class Heroes singer, Travie McCoy certainly took it to be about him: "I'm just stoked that she finally has a song with some substance on her record," he told MTV. "Good job."
Amy Winehouse's "Me & Mr. Jones"
Amy Winehouse's "Me & Mr. Jones"
A) Alex Clare
B) Pete Doherty
C) Blake Fielder-Civil
D) Nas
Answer: D) Nas
Although Winehouse dated EDM artist Alex Clare, had a fling with Pete Doherty and was married to Blake Fielder-Civil, she wrote "Me & Mr. Jones" about a friend: Nas. Real name Nasir Jones, the rapper confirmed Winehouse's track was about him after her death.
Alanis Morissette's "You Oughta Know"
Alanis Morissette's "You Oughta Know"
A) Dave Coulier
B) David Geffen
C) Ryan Reynolds
D) John Stamos
Answer: A) Dave Coulier
Alanis wrote this Jagged Little Pill diss track about Full House actor Dave Coulier, who she dated in the early 1990s.
As the inspiration for this boombox-in-the-air-worthy timeless hit, Rosanna Arquette (Gabriel's girlfriend at the time) is easily the luckiest person on this list.
The Beatles' "Got to Get You Into My Life"
The Beatles' "Got to Get You Into My Life"
A) Jane Asher
B) Mary Jane
C) Linda McCartney
D) Heather Mills
Answer: B) Mary Jane
Paul McCartney's Revolver track wasn't about any of the ladies in his life: It was about marijuana. "It's actually an ode to pot," McCartney explained. "Like someone else might write an ode to chocolate."
Derek and the Dominos' "Layla"
Derek and the Dominos' "Layla"
A) Pattie Boyd
B) Bonnie Bramlett
C) Olivia Harrison
D) Yoko Ono
Answer: A) Pattie Boyd
In 1970, Eric Clapton wrote this song as a lovelorn plea to Pattie Boyd. The only problem? She was the wife of his best friend, George Harrison. Much speculation and three years later, Boyd and Harrison divorced and she remarried Clapton in 1979. After that, she inspired his solo hit "Wonderful Tonight" and the two lived happily ever after until divorcing in 1989.
