The Best of Early 2000’s Celebrity Break-Up Songs

“Cry Me a River” (Image Credit: Zomba Recording LLC)

Taylor Swift might be the reigning Queen of the break-up song when it all goes sour but she ain’t the only one to pen a song about a nasty break-up. Celebs have been airing their dirty laundry for all to hear via their music for a long time! Sometimes it even ends in a war, just ask Eminem and Mariah…

Here’s a few of the best revenge songs for you all.

Justin Timberlake – ‘Cry Me  A River’ (2002, reportedly about Princess of Pop & X Factor judge, Britney Spears)

The History: This picture perfect couple with their squeaky clean image dated from 1999 – 2002. Having met in the ‘Mickey Mouse Club’ 11 years earlier these two seemed like a match made in heaven! (let’s be honest, we all live in hope that one day they’ll get back together, sorry Jessica & Jason..) Then one day out of the blue it was all over. Justin found hair clippers and Britters found, erm.. another man? JT’s hit  Cry Me A River , reportedly about Spears cheating, was released in 2002 soon after the shock split and features a Britney lookalike in the video.
The Lyrics: “You don’t have to say what you did/I already know, I found out from him/Now there’s no chance for you and me, they’ll never be/And don’t it make you sad about it?”

Britney Spears – ‘Everytime’ (2004, reportedly about Justin Timberlake)

The History: See the above, is this Britney’s reply to Cry Me A River? Just like JT’s video, fans assumed that Stephen Dorff who plays Britney’s boyfriend in the video was meant represent Justin, going on to guess that fame made their relationship claustrophobic among a million other interpretations. (we just wanna know what happened!) One thing we can be sure of is that the lyrics were about her messing up a past relationship.. *cough Justin cough*

The Lyrics: “I may have made it rain/Please forgive me/My weakness caused you pain/And this song’s my sorry/At night I pray/That soon your face will fade away…I see your face/You’re haunting me/I guess I need you baby”

Pink – ‘So What’ (2008, about Carey Hart)

The History: When the feistiest girl in pop split up from her motocross heart-throb Carey Hart, it was probably the most amicable split in celeb history, all history for that matter. He even appeared in the video, as himself. It’s okay now though, they reunited and had baby Willow, awk! It’s not all doom and gloom.

The Lyrics: “And guess what?/I’m having more fun/And now that we’re done/I’m gonna show you tonight/I’m all right, I’m just fine/And you’re a tool.”

Katy Perry – ‘Circle The Drain’ (2010, reportedly about Travie McCoy)

The History: This cute couple dated for several years but split not long after the Gym Class Heroes front man promised to put a ring on Katy’s finger in 2009. Katy described the angry track as  ‘kinda like my You Oughta Know‘ moment and takes a swipe at Travie’s drug addiction. The 6’4 vocalist said he’d never heard the track but that he was ‘just stoked that she finally has a song with some substance on her record. Good job’ ouch!

The Lyrics: “Thought that I was the exception/I could reroute your addiction/You could’ve been the greatest/But you’d rather get wasted/You fall asleep during foreplay/’Cause the pills you take/Are more your forte/I’m not sticking around to watch you go down/Wanna be your lover/Not your [bleepin’] mother.”

Taylor Swift – ‘Forever & Always’ (2008, reportedly about Joe Jonas)

The History: Taylor has a thing for writing about her exes and she makes no secret of it either, saying  “If you’re horrible to me, I’m going to write a song about you, and you are not going to like it. That’s how I operate. If guys don’t want me to write songs about them, they shouldn’t do bad things!” ..well that’s them told! ‘Forever & Always’ is just the first of what would be  one of her many break-up songs. It’s about then boyf, Joe Jonas who she was dating during Summer ’08, that was until he dumped her during a 27 second phone call – Revenge is sweet. Joe replied with Much Better an obvious swipe at the country beauty, even referencing her song Teardrops On My Guitar.

The Lyrics: “Was I out of line?/Did I say something way too honest?/Made you run and hide like a scared little boy/I looked into your eyes/Thought I knew you for a minute/Now I’m not so sure.”

Eminem – ‘Bagpipes From Baghdad’ (2009, there’s no doubt this is about Mariah Carey)

The History: Em claims that he and Mariah had a fling back in 2001,  which she has repeatedly denied, much to his annoyance. Back in ’05 he even played alleged voice mails from Mimi before playing his song Puke live. He also referenced her in Superman and When the Music Stops off The Eminem Show LP before taking another swipe in this track off his Relapse album, pretty funny if you ask me!

The Lyrics: “Mariah, whatever happened to us?/Why did we have to break up? … /Nick Cannon better back the [bleep] up/I’m not playing/I want her back, you punk.

Mariah Carey – ‘Obsessed’ (2009, 100% about Eminem)

The History: See the above, this was Mariah’s response to Slim Shady’s Bagpipes From Baghdad and all the other digs/mockery that came before it. Although she denied that the song was a diss at the rapper, she erm.. went and dressed up as a bearded version in the video.. Eminem didn’t take the dig lightly and hit back with The Warning in which he has some very choice words for the singer, Eminem 1, Mariah 0.

So there you have it, nothing gets the creative juices flowing quite like a broken heart! Affairs of the heart are always an interesting subject but when there’s two celebs involved, that’s when it all gets that little bit more captivating and whether you want to admit or not, we all love a bit of nostalgic celeb gossip!


Originally posted November 8, 2012

Sheree J

Sheree Jackson
Hey, I’m Sheree. Music makes the world go round, as do cups of tea, cocktails, laughter, and nights out. It’s all about the little things in life.
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