17 songs that got you through your breakup in the ’00s

Wallow with us.

September 22, 2015

Breakups suck no matter which way you slice it, and music is one of the many things that attaches itself to our relationships whether we like it or not. For every song about the happiness of love, there are a hundred more about the pain and suffering of heartache.

By the end of the ‘00s, an impressive collection of new tunes made their way into the world’s broken hearts. Even listening to these songs years later can provoke the same emotional turmoil it did the first time around.

Because we still love to torture ourselves, see if this shortlist of classic breakup jams from the ‘00s somehow found their way onto your playlist.

Macy Gray – “I Try” (2000)

She may have been a one hit wonder, but at least Macy Gray gave us one of the most important breakup songs of 2000 with “I Try.” It’s an important song because it outlines perfectly how everyone feels when the love is gone—trying to play it cool but NOTHING is cool when your heart is a mess. The song peaked at number five in the US and won Macy Gray Best Female Pop Vocal Performance at the 2001 Grammy Awards.

Justin Timberlake – “Cry Me a River” (2002)

What makes this song so juicy is the rumours surrounding it—that Justin Timberlake and producer Scott Storch penned the song as an ode to Justin’s failed relationship with Britney Spears. Those rumours held their weight when the music video revealed an actress who looked nearly identical to Britney. The lyrics suggest the relationship was all cheating and lies, further fueling the publicity surrounding the song and the pop stars’ disastrous relationship. Britney Spears would later shoot back with her own song about the time they spent together (MORE ON THAT LATER).

Ashanti – “Foolish” (2002)

Our one-time princess of hip-hop and R&B, Ashanti ruled the airwaves during the first half of the ‘00s. Arguably one of her most successful tracks, “Foolish” hit all the right marks for those of us trying to mend a broken heart. The music video was an homage to the film Goodfellas and featured Terrence Howard as Ashanti’s love interest. The song spent 10 weeks at number one on the Billboard Hot 100 and has forever remained a staple on our heartbreak soundtrack.

Britney Spears – “Everytime” (2003)

She has neither confirmed nor denied it, but many believe Britney Spears’ massive hit “Everytime” to be a response to ex Justin Timberlake’s “Cry Me a River.” The depressing love ballad was also Britney’s first attempt at writing her own music. She partnered with backup vocalist Annet Artani to compose and write the lyrics, and critics were impressed. The video is Britney’s most powerful—the singer plays a version of herself fighting with a boyfriend, being hounded by the media, and ultimately drowning in a bathtub. The original version had Britney overdosing on drugs, but that idea was met with too much heat.

Kelly Clarkson – “Since U Been Gone” (2004)

That one song you can scream at the top of your lungs with the car windows rolled down is KEY in a breakup, and “Since U Been Gone” most certainly fills that role. After being passed up by P!nk and Hilary Duff, Kelly Clarkson was offered the tune and ultimately made it the perfect breakup jam that it is today. The lyrics are written from the perspective of finally accepting the fact that leaving her volatile relationship is better than staying and being miserable — something we’ve all been guilty of.

Eamon – “I Don’t Want You Back” AKA “F**k It” (2004)

This song has so much angry cursing that it’s almost unbearable to listen to the edited version. Despite its success as a dramatic breakup song, “I Don’t Want You Back” was reviewed by many as a marketing ploy and manufactured move by Eamon’s record company. Subsequently the response song “F**k You Right Back” by Frankee was seen as nothing short of some executives trying to make some bank off of the original’s success. They even went so far as to claim Frankee was Eamon’s ex, but that turned out to be a huge lie as well.

Usher – “Burn” (2004)

Coming off the success of “Yeah!” Usher released second single “Burn” from 2004’s Confessions to wide praise. Rumours flew that the song Usher co-wrote came from a deep personal experience in love and loss. Those rumours have never been confirmed, but the ballad lives on in our hearts and mind as one of the saddest and truest songs about the bitter end of any relationship.

Beyoncé – “Irreplaceable” (2006)

Quite possibly the most important empowering 2000’s breakup jam, Beyoncé’s “Irreplaceable” had everyone preaching “to the left, to the left” any time they were going through a breakup. The song is about a woman that is kicking her unfaithful man out of the house and gives way for all women to own their sexual destiny by claiming they can find someone better in less than 24 hours. The single became Beyoncé’s most successful track from her second studio album and helped set the tone for the future of Queen B and her many winning moments.

Timbaland Feat. OneRepublic – “Apologize” (2006)

It’s whiny and completely overdramatic and that is precisely why “Apologize” still makes a tear come to your eye today. The original version features a sepia-toned music video with lead singer Ryan Tedder playing piano while he sings. The remixed version by Timbaland gave way for the official release of a music video and is considered the stronger version of the two. Either way that piano will strike a chord within you every single time.

Fergie – “Big Girls Don’t Cry” (2007)

“Big Girls Don’t Cry” tackles a woman’s bravery in ending a relationship and in doing so, finding the room to grow and be independent. It was a number one hit in Canada and stayed on the Hot 100 chart for fifty (!) weeks. The music video features Jess (Milo Ventimiglia) from Gilmore Girls as Fergie’s love interest covered in tattoos. That is all.

Kanye West – “Heartless” (2008)

Kanye West has blessed us with countless wonderful things in this life, one of which is the perfect “Heartless.” This Kanye track adds just enough condescending lyrics to remind you consistently that you are listening to a song written by a man that thinks the world revolves around him.

Rihanna – “Take a Bow” (2008)

Clocking in as Rihanna’s third number one hit (at the time), “Take a Bow” was the perfect melody to curl up to when you were feeling sad in 2008. Some critics praised the song’s mature lyrics and pop ballad contribution; others called it weak and completely unoriginal. That argument can be dissected to bits, but for now we will accept it for the breakup anthem that it is.

Lady Antebellum – “Need You Now” (2009)

If you don’t know this song it is very possible you were asleep during the entirety of 2009. After all, “Need You Now” did win Song of the Year and Record of the Year at the 2011 Grammy Awards and spent five weeks at number one near the end of 2009. The pop-heavy country song was a huge crossover hit and touched any music fans’ hearts regardless of genre preference. It was also one of the most overplayed songs of that year making it both loathed and loved by the public.

Adele – “Rolling In the Deep” (2010)

This and pretty much every track on Adele’s blockbuster record 21 can be deemed the ultimate breakup song. “Rolling In the Deep” was the track that propelled Adele into super stardom in North America and made 21 inescapable in 2010. The song plays perfectly to the lover scorned.

Cee Lo Green – “Fuck You” (2010)

Known by various titles thanks to its profane lyrics, Cee Lo Green’s “Fuck You” was a surprising hit back in 2010. With its upbeat nature and off-the-cuff lyrics, this Cee Lo song was showing up on our radio, TV, and iTunes lists whether we like liked it or not. It’s fun in nature but still gets across the message that when love goes wrong sometimes all you can say is: Fuck you.

Eminem Feat. Rihanna – “Love the Way You Lie” (2010)

There has been much speculation that Eminem chose Rihanna to sing the chorus of his highly successful single “Love the Way You Lie” due to the tumultuous relationship they had with their respective lovers Kimberly Scott and Chris Brown. The lyrics refer to a relationship where neither person wants to walk away, despite knowing how bad they are together. It was a massive success and inspired Rihanna to record a follow-up in “Love the Way You Lie Part II” sung mainly from her point of view.

Gotye Feat. Kimbra – “Somebody That I Used To Know” (2011)

You may have heard it countless times during the year (and the next year) of its release, but “Somebody That I Used To Know” is still a song we scream along to every time we hear it. The breakout hit from Gotye’s third studio album brought him to the forefront of popular music worldwide, specifically in North America. The song looks at Gotye’s experience with past relationships while successfully expressing how we all feel after a relationship fails miserably.


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