1. Justin Timberlake - “Cry Me A River”
You don’t have to say, what you did / I already know, I found out from him / Now there’s just no chance, for you and me, there’ll never be / And don’t it make you sad about it
Did Britney Spears cheat on Justin? Maybe. That’s the word on the street, anyway. His response? A pretty classy “K bye” jam.
2. Katy Perry - “Wide Awake”
I wish I knew then / What I know now / Wouldn’t dive in / Wouldn’t bow down / Gravity hurts / You made it so sweet / Til I woke up on / On the Concrete
Katy Perry’s quick marriage to Russell Brand and subsequent divorce was brilliant fodder for this catchy song. It seems to say “MAN, life is cool when it’s not spent being married to Russell Brand.” In so many words.
3. Mariah Carey - “Obsessed”
Tellin’ the world how much you miss me / But we never were, so why you trippin’ / You a mom and pop, I’m a corporation / I’m the press conference, you a conversation
According to Mariah, she and rapper Eminem never really dated. But…something seems to have gone down. What else would inspire her to dress up as him, stalk herself, and get hit by a bus? In a music video? These are the questions.
4. Taylor Swift - “Dear John”
Dear John, I see it all now it was wrong / Don’t you think nineteen’s too young / To be played by your dark twisted games / When I loved you so? I should’ve known.
TSwift has a long, storied history of writing about train wreck relationships. That much is known. She dropped the song bomb on John Mayer after their tumultuous relationship ended, and all was well, until…
5. John Mayer - “Paper Doll”
Paper doll, come try it on / Step out of that black chiffon / Here’s a dress of gold and blue / Sure was fun being good to you
Mayer’s alleged response. Good on ya, John.
6. Dixie Chicks - “Goodbye Earl”
Right away Mary Ann flew in from Atlanta / On a red eye midnight flight / She held Wanda’s hand and they worked out a plan / And it didn’t take them long to decide / That Earl had to die
Straight and to the point. This Dixie Chicks classic doesn’t target one dude - rather it’s more of a cautionary tale to anyone considering becoming an abusive significant other.
7. Alanis Morissette - “You Oughta Know”
And I’m here to remind you / Of the mess you left when you went away
By now we all know the rumors about this song - that it’s written about Uncle Joey. And we’re all still just as confused as the day we were informed.
8. Ani DiFranco - “Napoleon”
You had an army / Of suits behind you / And all you had to be was willing / And I said I still / Make a pretty good living / You must make a killing
Speaking of Alanis Morissette - rumor has it that this song was written about her. Ani was one of the first ladies to establish her own independent label, as she felt strongly about keeping her creative freedom. Supposedly this jam was a jab at a certain 90’s era ladysinger who ended up going the route of the dreaded record label.
9. Sara Bareilles - “Love Song”
I’m not gonna write you a love song / ‘Cause you asked for it / ‘Cause you need one, you see
AND SPEAKING OF BIG RECORD LABELS - it’s been said that Sara wrote this song as a little “back off” anthem. Apparently she didn’t take kindly to record execs forcing her to write a love song when she wasn’t feelin’ it.
10. Lynryd Skynryd - “Sweet Home Alabama”
Well, I heard Mister Young sing about her / Well, I heard ole Neil put her down / Well, I hope Neil Young will remember / A Southern man don’t need him around anyhow
When Neil Young dissed Alabama for its history of racism and slavery, Lynryd Skynryd fired back, saying “We thought Neil was shooting all the ducks in order to kill one or two.” Fair enough.
11. Bob Dylan - “It Ain’t Me, Babe”
But it ain’t me, babe / No, no, no it ain’t me, babe / It ain’t me you’re lookin’ for, babe
Bob and Joan Baez dated in the 60’s, but broke up during a concert tour in 1965. And even though it’s been covered by countless musicians - including Joan herself - it’ll always sound best in that raspy, bitter tone.
12. The White Stripes - “Blue Orchid”
How dare you, / How old are you now, anyway?
Jack White of The White Stripes and Renee Zellweger dated - did you know that? Whether or not this song is about her is still up for debate. Still juicy, though.
13. Carly Simon - “You’re So Vain”
You’re so vain / I’ll bet you think this song is about you / Don’t you, don’t you
No one knows for sure who this song is about. Carly is keeping mum. And that’s fine, as revealing the answer would sort of defeat the purpose of the song - but people keep guessing. Could be Mick Jagger, David Bowie, David Cassidy, Cat Stevens, Kris Kristofferson, Warren Beatty…well, Carly was very popular in the 60’s.