“I must have called a thousand times to tell you I’m sorry.” “Is it too late now to say sorry?” Between Adele and Justin Bieber’s respective pop mega-hits, music was filled with apologies in 2016 (when this piece was first published). But the regretful songwriter is far from a new trend. Throughout the years, hundreds of musicians have tried to say sorry for, more often than not, a romantic mistake. In addition to the apologetic tracks from Adele, Bieber and many more, these songs prove whether you’re a huge pop star, a quiet folk artist, or somewhere in between, love sometimes does mean having to say you’re sorry.
1. “Apologize,” One Republic ft. Timbaland
Remember in 2007 when no matter how hard you tried to escape this song, you couldn’t? Thanks to a touch of Timbaland, the R&B remix of “Apologize” was all over the radio, played during pinnacle emotional moments in movies and TV shows, and was probably a key track in that breakup mix CD you made or received. “Apologize,” both the original and remix version, is packed with regret, dramatics, and sap that all come to a peak in the catchy and cringe-worthy, falsetto filled, chorus. —Laura Stanley
2. “So Sorry,” Feist
“I’m sorry. Two words I always think after you’re gone.” Leslie Feist’s song of regret is a simple but moving one. Feist emotionally apologizes for being selfish, made even more poignant by her expressive vocals, in an effort to prevent a future apart from her lover. Amongst a simple folk soundscape, “So Sorry” dwells on past actions and wonders if something else had been said or done, would things be different. —Laura Stanley
3. “Please Forgive Me (Song Of The Crow),” William Fitzsimmons
Soft-spoken folk troubadour William Fitzsimmons’ 2008 album The Sparrow and the Crow was heavily influenced by his divorce, so needless to say there’s a lot of remorse in it. On “Please Forgive Me (Song Of The Crow),” Fitzsimmons acknowledges his mistakes and destructive demons and asks to be forgiven. Like Feist, Fitzsimmons’ apology is straightforward but by packing so much emotion into his trembling voice, it’s clear that this apology was years in the making. —Laura Stanley
4. “Ms. Jackson,” Outkast
Apologizing to a lover happens a lot in songs, but apologizing to the mother of an ex-partner is a creative feat no one has done as well as Outkast. André 3000 and Big Boi’s narrator expresses remorse over what happened between him and the daughter of Ms. Jackson. Along with his apology, most memorably done in the song’s ultra-catchy hook “I’m sorry Ms Jackson, I am for real. I never meant to make your daughter cry, I apologize a trillion times,” Outkast’s narrator wants to prove to Ms. Jackson that although his relationship ended with her daughter, he will always support her grandchild. —Laura Stanley
5. “Purple Rain,” Prince and the Revolution
In the pop wonder that is “Purple Rain,” Prince pours the grief of his narrator into super soulful and emotional verses and wailing guitar solos. As an outsider looking in on a relationship that won’t end, the narrator wants only the best for the one he lusts after, admitting, “I never meant to cause you any sorrow. I never meant to cause you any pain.” Clocking in at almost nine minutes, “Purple Rain” is the perfect self-indulgent length for when you find yourself dwelling on romantic mistakes. —Laura Stanley
6. “All Apologies,” Nirvana
Written by Kurt Cobain for his wife and daughter, Nirvana’s “All Apologies” is heartbreaking. In the last track of Nirvana’s final album In Utero, Cobain is tired and has found peace in knowing, “Everything is my fault, I’ll take all the blame.” Away from Cobain’s personal struggles, “All Apologies” captures the regret many of us feel about the terrible things we do how we’re sometimes unable to stop doing them. —Laura Stanley
7. “The Apology Song,” The Decemberists
Like many apologetic tracks, “The Apology Song” focuses on a loving relationship that came to an unfortunate end. The relationship in this case though is a man and his bicycle. The Decemberists’ frontman Colin Meloy is very remorseful when the bike his friend Steven leaves him to temporarily care for gets stolen outside a grocery store. Poor Steven even had a name for his bicycle (Madeleine) before the tragic mishap takes place so it’s no wonder Meloy is so sorry. —Laura Stanley
8. “Party Song,” Keaton Henson
In what is the exact opposite of a typical-sounding party song, Keaton Henson apologizes to his ex for not attending their party. His excuse? He’s afraid he will kill her new lover. In the honest and super dark “Party Song,” Keaton holds nothing back, including an apology that is filled with an equal amount of regret and self-loathing—a common mix of emotions behind an apology. —Laura Stanley
9. “One of Us Must Know (Sooner or Later),” Bob Dylan
This organ-driven Blonde on Blonde track evokes the kind of situation where no one in particular—or perhaps everyone—is at fault, making Bob Dylan’s apology more of a post-mortem than anything else. “I didn’t mean / To treat you so bad / You shouldn’t take it so personal,” he wheezes in its opening lines, regretful and defensive at the same time, as eager to justify where he went wrong as he is to make things right again. There’s something inherently human about apologizing, retracing our missteps so we can get better, and sooner or later, we reach an understanding of our nature. —Scott Russell
10. “Swallow My Pride,” The Ramones
There’s nothing quite so humbling as admitting you’ve done wrong—it takes a self-awareness and vulnerability that many find difficult to stomach. Joey Ramone swallows his pride nonetheless on this Leave Home track, a classically Ramones rocker that plays coy about making any actual apology, but is all the better for it. “Things were looking grim but they’re looking good again,” Ramone observes, mumbling the refrain of “Swallow my pride” at first, then singing it out. What exactly went wrong remains vague, but the value of putting a greater good before yourself shines through. —Scott Russell