John Mayer’s ‘Shadow Days’ About Jennifer Aniston & More Break-Up Songs (Photos)

John Mayer’s single ‘Shadow Days’ is about Jennifer Aniston, reports Us Weekly. See other breakup songs.

Henny Ray Abrams / AP Photo ; Markus Schreiber / AP Photo

Henny Ray Abrams / AP Photo ; Markus Schreiber / AP Photo

“Shadow Days” by John Mayer

How Bitter Is It? 2 of 10. With a mopey country twang and apologetic lyrics, “Shadow Days” is more about Mayer’s realization that he was a total douchebag during the relationship than it is about getting revenge.
Sample lyrics: “Well I’m not some troublemaker / And I never meant her harm / But it doesn’t mean I didn’t make it / Hard to carry on”

Backstory: It looks like John Mayer may have learned a thing or two about autobiographical songwriting from his ex-flame and fellow singer-songwriter Taylor Swift. While Swift penned her vindictive hit “Dear John” about their botched relationship, Mayer apparently wrote his latest single “Shadow Days” about his breakup three years ago with actress Jennifer Aniston. Sources told Us Weekly, “’Shadow Days’ is about Jen. It really took him a long time to get over her. He really loved her a lot. He wrote the song as a farewell letter knowing [Jen] would hear it. Ultimately, he’s done a lot of self-reflection though and he realizes they weren’t right for each other.”

Kevin Mazur, Wire Images / Getty Images

“Rolling in the Deep” by Adele

How Bitter Is It? 9 of 10. Though most of the songs on 21 convey heavy heartbreak, “Rolling in the Deep” is Adele’s revenge song. She takes what she and her heartbreaker could have had, dangles it in front of his face, then stomps all over him. She’s gonna make him regret this, she promises.

Sample lyrics: “Baby I have no story to be told / But I’ve heard one on you / And I’m gonna make your head burn / Think of me in the depths of your despair / Making a home down there / ‘Cause mine sure won’t be shared”

Backstory: We might finally know who broke Adele’s heart and inspired the Grammy-winning, record-busting hit album of 2011, 21. Britain’s Heat magazine claims the mystery man is 31-year-old photographer Alex Sturrock. An anonymous “friend” of Sturrock tells the magazine that Sturrock and Adele dated from the summer of 2008 until April of 2009, a month before Adele began recording 21. Sturrock’s website also features several portraits and candid shots of a very happy-looking Adele, who hired him as the official photographer for her U.S. tour, according to the source. The pair reportedly shared hotel rooms while traveling and he was there to capture her Grammy win in 2009. “They spent all their time together—and when they weren’t together they would ring each other constantly,” the friend said. Despite the connection the friend claims the pair had—and despite that he was living with her at her West London home—Alex reportedly refused to call Adele his girlfriend and the two eventually split. Adele has not confirmed the identity of her former lover, letting the album speak for the relationship.

Noel Vasquez / Getty Images; Frederick Breedon, WireImage / Getty Images

“Dear John” by Taylor Swift

How Bitter Is It? 10 of 10. Swift's new album is already getting raves, and the press from her latest breakup song isn't hurting, either.

Sample Lyric: "Don't you think I was too young to be messed with? / The girl in the dress/ Cried the whole way home / I should've known"

Backstory: Taylor Swift's new album, Speak Now, features "Dear John," an angry six-and-a-half minute song reportedly written about another musician: John Mayer. Though Swift won't confirm that Mayer is the subject of the song, they were linked in 2009 while they collaborated on a song from his last album, "Half of My Heart." And Swift has a track record of writing songs about exes, penning "Back to December" for Taylor Lautner, and "Forever & Always" about Joe Jonas. New York Times music critic Jon Caramanica writes of "Dear John:" "Whatever he did—or whatever Ms. Swift would like to suggest that he did—must have been brutal."

KMazur, WireImage / Getty Images; Jeff Christensen / AP Photo

“Ms. Jackson” by OutKast

How Bitter Is It? 2 of 10. If you are going to talk about baby-mama drama, it's best to do it to this beat, which scored the duo a Grammy Award in 2002.

Sample Lyric: "She never got a chance to hear my side of the story we was divided / She had fifths out, cookouts, on my child's birthday I ain't invited"

Backstory: Andre 3000's ode to the mother of his "baby drama mama" is more apology than assault. The upbeat but assertive track is an attempt to explain himself to the mother of his ex-girlfriend—his baby's momma—Erykah Badu, with whom he had become estranged. Badu, who wrote her own song about the breakup says any bad blood is in the past. "My mom just laughs about ‘Ms. Jackson,'" she says, "She and Dre are really pretty cool; they talk."

Michael Ochs Archives / Getty Images; Time Life Pictures / Getty Images

“You're So Vain” by Carly Simon

How Bitter Is It? 5 of 10. The original I-hate-my-ex song. Simon's track is too smooth and melodious to really hit the bitter charts, but her lyrics pack a punch.

Sample Lyric: "Well you said that we made such a pretty pair, and that you would never leave / But you gave away the things you loved and one of them was me"

Backstory: Simon's tune is probably the most notorious and mysterious of all payback songs. In 1972 she belted out the story of her and a "vain" ex who traveled to Nova Scotia and Saratoga. Rumors began to fly that the song was about James Taylor, whom she had just married before the song debuted. But the most recent suspicion is on her former boss at Elektra Records, David Geffen. Simon says no. The two most popular guesses for the song's inspiration: former beaus Mick Jagger or Warren Beatty.


“You Oughta Know” by Alanis Morissette

How Bitter Is It? 10 of 10. It doesn't get any more vengeful than this song. It's a classic 1990s breakup tune, with the right blend of sarcasm and snark all rolled into a musical finger flip.

Sample Lyric: "And every time you speak her name, Does she know how you told me you'd hold me / Until you died, till you died, But you're still alive"

Backstory: It only took comedian and former Full House star Dave Coulier 13 years to tell the press that Morissette's angsty hit song was written about their turbulent relationship. It turns out that after the song came out, Coulier and Morissette sat down and hashed things out, and have been cordial ever since.

Kevin Mazur, WireImage / Getty Images; AP Photo

“Cry Me a River” by Justin Timberlake

How Bitter Is It? 9 of 10. Though the song may inspire nostalgia at any dance club, Justin Timberlake's music video is a crystal clear, hostile fuck you to his ex-girlfriend Britney Spears. In the video, he sings about the demise of his Mickey Mouse Club sweetheart and begins to trash a Spears lookalike's house. He kicks a framed photo of the two and videotapes a makeout session with a brunette on Spears' bed. Who needs therapy?

Sample Lyric: "I know that they say, that somethings are better left unsaid, It wasn't like you only talked to him and you know it"

Backstory: After their three-year relationship ended in 2002, rumors spread that Britney Spears was unfaithful. Then Timberlake released "Cry Me a River," which went on to win a 2004 Grammy. But where his song is seething with anger, Spears' retaliation in 2004, with her song " Everytime", is weepy and dramatic. The video depicts her downward-spiraling relationship with a faux Justin Timberlake and her own faux death.

Kevin Winter / Getty Images; Matt Sayles / AP Photo

“What's Left of Me” by Nick Lachey

How Bitter Is It? 6 of 10. It's hard to feel the anger in such a weepy song, but Nick Lachey manages it. Especially with the video that mimics his oddball marriage to singer Jessica Simpson.

Sample Lyric: "Now I'm broken, and I'm faded, I'm half the man I thought I would be, But you can have what's left of me"

Backstory: After only three years of marriage, which included a freak-show MTV reality series, Newlyweds, Jessica Simpson and Nick Lachey parted ways. But rather than post-divorce therapy, the two pop singers drummed up some post-divorce songs. Simpson's album A Public Affair tanked, while Lachey's What's Left of Me reached No. 6 on the Billboard chart. Who needs alimony when you got record sales?

Getty Images

“Layla” by Eric Clapton

How Bitter Is It? 1 of 10. This song did eventually lead to a marriage, so it can't be all bad.

Sample Lyric: "Make the best of the situation before I finally go insane / Please don't say we'll never find a way, Or tell me all my love's in vain"

Backstory: It's one thing to sing about an ex-girlfriend, but it's quite another to sing about another man's wife. That's what happened with "Layla," Eric Clapton's 1972 hit, which he wrote about his love for Pattie Boyd, wife of his close friend George Harrison. According to Boyd, when Clapton finally confessed his feelings to the couple, nothing much changed, and the three stayed close. But Boyd eventually divorced Harrison in 1974, and married Clapton five years later, though the two also later divorced.

Chris Pizzello / AP Photo; Katy Winn / AP Photo

“Cold Case Love” by Rihanna

How Bitter Is It? 5 of 10. More tragic than bitter, the song is Rihanna's goodbye to her abusive ex-boyfriend, Chris Brown.

Sample Lyric: "Your love was breaking the law / But I needed a witness / So pick me up when it's over / It don't make any difference / Will it ever be solved / Or am I taking the fall / Truth was there all along / Tell me how did we miss it"

Backstory: After such a public and violent breakup from singer Chris Brown, it was natural that Rihanna would conjure up a song to combine her voice with her heartache. In 2009 the singer was beaten by Brown in Los Angeles; she acknowledged the song was about the emotional aftermath of dealing with her domestic abuse.

Dana Nalbandian / Getty Images; Getty Images

“Violet” by Courtney Love

How Bitter Is It? 8 of 10. One rock star trashes another—with fatal consequences for his hair.

Sample Lyric: "Go on take everything / Take everything, I dare you to / I told you from the start / Just how this would end."

Backstory: Bitterness takes on new meaning at the hands of Courtney Love who, as lead singer of Hole, wrote "Violet" in 1995. The angry song is reportedly about her ex-boyfriend, Smashing Pumpkins frontman Billy Corgan, whom she dated before her marriage to Kurt Cobain. Needless to say, things ended badly—and Love later described "Violet" as a "song that's about a jerk, I hexed him and now he's losing his hair."

Charles Sykes / AP Photo; Chris Pizzello / AP Photo

“7 Things” by Miley Cyrus

How Bitter Is It? 5 of 10. Smack-dab in the middle—while Miley Cyrus belts out the seven things she hated about former beau Nick Jonas, including showing a photo of them with Jonas' face covered, she leaves her song and music video on a sweet note about the seven things she did inevitably like about young Jonas: a perfect happy ending to a tween breakup.

Sample Lyric: "It's awkward and it's silent, as I wait for you to say, what I need to hear now, your sincere apology, when you mean it, I'll believe it, if you text it, I'll delete it"

Backstory: Nick Jonas and Miley Cyrus broke up in 2007, supposedly because of Jonas' infidelity. That just goes to prove that you can't piss off Miley Cyrus, because not only will she make a fierce song about the seven things she hates about you, but she'll lay down the guilt as well. Cyrus' song was so sweet and sour that the two reunited again for a brief period until, like young lovebirds do, they inevitably broke up. That might be the reasoning behind her new song "Giving You Up," after her second go-round with Jonas.

Martial Trezzini / AP Photo; Eric Jamison / AP Photo

“So What” by Pink

How Bitter Is It? 8 of 10. Pink may be "all right," as her song suggests, but she fights off crazy fits of tears and wreaks havoc on heart-carved trees and guitar shops in her music video. This isn't bitter—it's borderline psycho. Heartbreaker ex Carey Hart also makes his cameo in the video. Pink coyly teases him, which suggest she's still hung up on the guy. Poor sap.

Sample Lyric: "You weren't there, you never were, you want it all but that's not fair, I gave you life, I gave my all, you were there, you let me fall"

Backstory: Carey Hart and Pink (real name Alecia Moore) have always had a rocky relationship. After they first started dating in 2001, they endured a few breakups before Pink proposed to the Motocross racer in 2005 during one of his races in California. After two years of marriage, Hart was reportedly caught cheating on his wife at a Hollywood night club, and the couple separated but told the press they remained friendly. Last year, the couple reunited and celebrated their fourth anniversary in January. Perhaps Pink released all her aggression on her 2008 track "So What." The music video showed the couple's friendly and sarcastic side, even with the tabloid drama surrounding their breakup.

Rick Maiman / AP Photo; Evan Agostini / AP Photo

“My Favorite Mistake” by Sheryl Crow

How Bitter Is It? 4 of 10. The song is too sweet to be bitter. If Crow's relationship with singer Eric Clapton was a mistake, at least it's her favorite one.

Sample Lyric: "I woke up and called this mornin', the tone of your voice was a warnin', that you don't care for me anymore, I made up the bed we sleep in, I looked at the clock when you creep in, it's six a.m. and I'm alone"

Backstory: Eric Clapton and Sheryl Crow dated for a brief time back in 1996, but they've kept their relationship cordial. It's been long-rumored that Crow wrote the 1998 hit about her time with Clapton, but she has never confirmed the story, saying only that the song is about the men in her life that weren't good for her. She's kept that information vaulted thanks to Carly Simon. If the song is about Clapton after all, then the two have clearly reconciled their differences, since Crow performed it with her ex-lover in 2006.

Kevin Winter / Getty Images; Gaye Gerard / Getty Images

“Go Your Own Way” by Lindsey Buckingham

How Bitter Is It? 8 of 10. The song seems more bittersweet than straight bitter, until you remember that Stevie Nicks had to sing backup vocals.

Sample Lyric: "Tell me why everything turned around. Packing up, shacking up, is all you want to do"

Backstory: At the end of a debauched and dramatic two months in Sausalito, California, recording Rumours, Lindsey Buckingham and Stevie Nicks split. Nicks tells Rolling Stone that Buckingham told her, "You take the car with all the stuff, and I'm flying back." And he did, and went to the Sunset Strip and recorded "Go Your Own Way." And for years the two of them sang it together onstage. Says Nicks, "I very, very much resented him telling the world that ‘packing up, shacking up' with different men was all I wanted to do. He knew it wasn't true. It was just an angry thing that he said. Every time those words would come out onstage, I wanted to go over and kill him."

Mark Allan, WireImage / Getty Images; Jon Kopaloff, FimMagic / Getty Images

“Digging in the Dirt” by Peter Gabriel

How Bitter Is It? 6 of 10. The song alternates between abusive ("Don't talk back / Just drive the car") and pleading ("Stay with me, I need support") in a way that, while unhealthy, isn't purely bitter. It's too introspective for that and, at the end of the video, when Gabriel's skeleton is reconstituted, dressed in white, and resurrected eating strawberries in a field of flowers, too optimistic, too.

Sample Lyric: "I'm digging in the dirt / To find the places I got hurt"

Backstory: Peter Gabriel worked on "Digging in the Dirt" and the album Us during a period that saw two failed relationships—his marriage to Jil Moore and his relationship with the actress Rosanna Arquette. He went into therapy; hence the "digging." Says Gabriel, "During this period I discovered the most unbelievable phenomena within myself, characteristics which I value for myself, but also characteristics with which I would rather not be confronted, like unlimited rage, or merciless hatred."