The Ex-Files: A Breakdown of Musical Breakup Songs

The other day I was driving and heard one of the most hauntingly beautiful songs from Adele that is also her latest single, "Someone Like You." I've heard her say that it was personally based on her ex-boyfriend, who she had hoped to marry. Now given that music has always dealt with heartache, I thought it would be interesting to do a summary on some of music's most memorable break-up songs and the artists behind them.

Adele, "Rolling in the Deep" and "Someone Like You"

This is arguably the year of Adele. Her album and singles have done tremendously well. She was covered on Glee and she stands to give one of the best performances at next week's MTV Video Music Awards. Her soulful, rich voice is what gives her both power and promise as one of music's true and lasting talents.
"Rolling in the Deep" is a classic kiss-off record. She proclaims that it was the guy's fault and that it was his mistakes that solidified the relationship's demise. The way she sings, you have no choice but to side with her. On the flip side, "Someone Like You" is a touching memorial. She laments the love lost, but is optimistic in finding a love like she had once before with an ex. No matter what kind of breakup you've been through, there's something in her delivery and her passion that remains with you. If she continues to make records like this, there's no question she'll be here to stay.

Beyonce', "Irreplaceable", "Single Ladies (Put A Ring On It)", "Best Thing I Never Had"

Beyonce' is amazingly one of pop's premier divas. And while she's always made chart-toppers; their respective outcomes have been mixed. Her latest album, 4, is steady on the charts and the latest single, "Best Thing I Never Had" is slowly catching on. While this latest single isn't steaming up the charts, it's proving that she wants to make build a catalog of diverse tunes that showcase her voice as much as her flare for the dramatic. "Single Ladies (Put A Ring On It)" is arguably one the biggest hits of her entire career. Danceable and devious, it lingers as much as it is fun but along the way you forget it's a breakup ditty. "Irreplaceable"  is her biggest breakup song, staying on the charts for a good chunk of 2006. And while everyone remembers the line, "to the left" it sounds to impersonal to really connect to it. No one, no matter how much wrong someone's done to you, they  shouldn't be made to feel like a couch. But then again, what do I know about hits?

Lauryn Hill, "Ex-Factor"

Lauryn Hill is someone who people will always remember for being bright enough and bold enough to take over the world, yet too weighed down to succeed at it. Her gigantic solo debut The Miseducation of Lauryn Hill, is all parts fun and thoughtful, frivolous and soulful. One of the best songs on the album, it flourished as a single. It's rumored that song is actually about the torrid affair she had with former bandmate Wyclef Jean, the way she sings it reminiscent of the old guard of Ella Fitzgerald and Sara Vaughn. You automatically side with her and for that the song is a modern classic, only improved upon by the music video.

Al Green, "How Can You Mend a Broken Heart", "For the Good Times"

Soul music wouldn't be the same without Al Green. Anytime you hear his music it takes you to a place that only few can take you. Lazy summers, collard greens, and flowing rivers are all images that come to mind when his voice hits your ear. His breakup songs are all the more wrenching for that because you know it comes from a deep, passionate place. "How Can You Mend a Broken Heart" is a well done cover of the Bee Gees early hit, but only slower so it sounds like you actually hear him cry at the end of the song. "For the Good Times" is another cover from crossover star, Kris Kristofferson and once again it takes you so far that it feels like you've moved hundreds of miles and a matter of minutes. If you really want to cry to a record, Al Green definitely is your man.

Christina Aguilera, "Fighter", "Hurt"

For someone with the voice of a large, troubled woman, Christina Aguilera hasn't much ventured into breakup territory. When she does, it's great. My only problem is, I'm not sure if she's talking about her long-estranged father or an ex. Her voice can cut through glass but the lyrics of "Fighter" to me seem to be about a friend or family member who cheated her rather than an ex boyfriend. The same can be said for "Hurt" which is beautiful, but is missing that one thing that separates it from being a great song rather than a good song. Or maybe I'm just too picky about breakup songs.

Carly Simon, "You're So Vain"

This is arguably the grandfather of breakup songs in pop. Carly Simon was so bitter, she never revealed who the song was about. But if any of her exes have heard this song at least once (which I'm sure of), they probably made sure to never cross her again. I mean this song is catchy, mysterious, and spiteful without completely going for the jugular. But I think for sure that this song is the blueprint for which breakup songs have been created since.

No Doubt, "Don't Speak," "Ex-Girlfriend"

No Doubt set the tone for 1990s groups. They were equal parts style and substance. But what they really get credit for is having two exes, Gwen Stefani and Tony Kanal not only work together but perform gut wrenching songs about their former romantic relationship. "Don't Speak" is what every angry teenage girl and twenty-something woman sang when their exes spurned them. To this day, it speaks volumes in the simplicity of the lyrics, not only lamenting the romance but the built-in friendship that came along with it. However, "Ex-Girlfriend" is arguably mad enough to send any guy running if he hears a girl playing it. It's funny and snarky all at once. And if the video's any indication Kanal and Stefani have managed to make great light of the love they once shared.

Justin Timberlake, "Cry Me A River," "What Goes Around...Comes Around"

There are several reasons I believe Justin Timberlake should make an album and an epic breakup song happens to be near the top of my list. Whether or not the songs are about any of his real-life exes is inconsequential, it's the dramatic disdain he manages to build into each one of the songs that make it a pleasure to listen to. "Cry Me A River" is not the jazz song you're grandmother probably had a 45 of, it's the song your cousin probably blasts in his or her dorm room around 2am. We all know who the song was about, but the video was the VMA-winning kiss-off that sent his career into the stratosphere as a solo artist. "What Goes Around...Comes Around" is "Cry Me A River's" angry little sister. She obviously wants more attention and gets it. While it was argued that it was based on the same subject as it's older brother, Timberlake has denied it. He said it was about a friend who was madly in love and ready to settle down when his friend's girlfriend ditched him for another friend. The friend is rumored to be JT's childhood best friend, Trace Ayala, the girl Elisha Cuthbert of 24 fame, and the other friend is hockey bad boy, Sean Avery. And looking at the video accompanying the song, it's interesting to note how similar-looking Elisha Cuthbert is to Scarlett Johansson. While we may never know the truth, it's highly arguable that Justin Timberlake has managed to turn heartbreak into pop mythology.

Are there any artists who I've should have focused on? Songs you like about heartbreak? Please let me know in comments.