Top 10 Breakup Songs to Cry Your Heart Out To

Cole Tessitore, Staff Writer

   Valentine’s Day is the holiday that celebrates love, but sometimes love is a heart-wrenching emotional minefield that leads to a breakup. Ending a relationship is hard, and there are a ton of ways to get through a breakup, like eating spoonfuls of ice cream straight out the carton, watching rom-coms and cheesy movies to numb the pain, and of course, listening to breakup songs. There are plenty of songs about love, and just about as many about breakups. Here are ten of the best breakup songs to listen to this Valentine’s Day.

10.) Cry Me a River by Justin Timberlake – The second single from his debut solo album Justified, a heartbroken Timberlake sings about his then ex, Britney Spears, after their highly publicized relationship and subsequent breakup. The song hints that Spears cheated on him, and Timberlake is totally over it, telling her to cry him a river. The mix of Timberlake’s recognizable, upbeat, pop-dance sound and his falsetto notes blend together perfectly, making this a breakup song that anyone can dance to as well.

9.) Everytime by Britney Spears – As a response to Justin Timberlake’s “Cry Me a River”, Spears released “Everytime”. A notable departure from her upbeat pop sound, Spears apologizes for her mistakes and infidelity. Written by Spears herself, the song is arguably one of the most personal songs from her discography. Complete with angelic harps, lyrics about realizing she is incomplete without Timberlake,  and her soft vocal delivery, “Everytime” is sure to be relatable to anyone missing his or her ex. 

8.) Who Knew by P!nk  – Although written about a friend that she lost to drug abuse, “Who Knew” has the same sentiment as that of one breaking up with a partner. Lyrically, the song is about looking back on a relationship and comparing how she never thought she would be apart from her friend, to what she knows now and how she is without him. She sings with so much emotion and heartbreak that the song can easily be counted as a breakup song.

7.) You Give Love a Bad Name by Bon Jovi – This infectious stadium anthem about a wicked ex is the quintessential 1980s rock song about a toxic relationship. Rather than a mournful breakup song, this anti-love jam is sure to have anyone mourning a breakup up on their feet and dancing to the beat of the drum. Not only is the song super catchy, but ‘80s hair bands are becoming cool again. There really isn’t a better way to be on trend and sing along to a good breakup song.

6.) Ex-Factor by Lauryn Hill – This breakup song encapsulates the issue of going back to an ex while fully knowing a breakup is inevitable. Hill explains that while knowing the relationship is doomed from the start every time they start over, she just cannot get over her love interest. Sonically, the song features a very tropical R-and-B atmosphere, a Santana-esque guitar solo after the bridge, and Hill’s soulful vocals. While still being a breakup song, it’s like the Groundhog’s Day version, where Hill keeps breaking up and getting back together with her partner over and over and over again.

5.) Irreplaceable by Beyoncé – Beyoncé gets very sassy in this song about kicking her ex out and throwing all his personal belongings out on the street. She makes it clear that he is disposable and he is out of his mind for thinking Queen Bey couldn’t find another just like him, or even better than him. Beyoncé effortlessly combines empowerment, anger, and heartbreak mixed with a bitter-sweet sentiment that there are plenty of fish in the sea.

4.) Wrecking Ball by Miley Cryus – One of the most talked about music videos of the 2010s, a fully nude Cyrus on a wrecking ball swinging around is one of the less subtle, yet still effective, metaphors for a breakup. The song features a synth and drum-heavy beat that harkens back to ‘80s breakup songs, complete with Cyrus’s forceful vocals. The full effect of “Wrecking Ball” really shines through with the accompanying music video with close up shots of a tearful Cyrus, displaying a new vulnerable side to the singer that hadn’t been showcased before. 

3.) Blank Space by Taylor Swift – The queen of breakup songs, Taylor Swift, cleverly plays into the narrative that she is notorious for dating some of the most famous men in the entertainment industry and then writing an uber popular breakup song about them after. Swift almost parodies herself by singing about how she is aware of her song writing habits, singing she will “write your name” after the relationship ends. “Blank Space” is a notable turning point for Swift, both personally and sonically. Swift features a more contemporary hip-hop influenced sound and an in-on-the joke perspective with her lyrics. 

2.) Thank U, Next by Ariana Grande – Similar to “Blank Space”, Grande is in on the joke, and she proclaims she is in fact thankful rather than regretful for all of her exes, who she then name drops in the opening lines of the song. Following the death of her Ex-boyfriend and Hip-hop-artist Mac Miller and the end of her highly publicized engagement to SNL Cast Member Pete Davidson, Grande explains that each of her previous past flames have taught her valuable lessons on love, patience, and pain. She also sings about focusing on self love and the importance of taking time to love yourself after a breakup. The song popularized the phrase “thank you, next” and has since become a sentiment that one can be grateful for the good times of a past relationship, but in the end it’s all about moving forward and looking ahead. 

1.) Un-Break My Heart by Toni Braxton – The breakup song to end all breakup songs, “Un-break My Heart” by Toni Braxton, the ‘90s R-and-B ballad outlines the blistering breakup between Braxton and her ex who left her. Throughout the song, Braxton conveys feelings of anguish and heartache through her dual use of breathy vocals on the verses and powerful, Whitney Houston-like vocals on the chorus. She begs for her ex to “un-break” her heart and to relieve her of all the emotional turmoil she has been through since the breakup. “Un-Break My Heart” perfectly captures every thought, feeling, and emotion that runs through a brokenhearted person. The song will have you crying, singing along with it, and pressing replay to hear it over and over again, making it the ultimate breakup song.