Shady Songs Musicians Wrote About Their Ex

It is a truth universally acknowledged that breakups suck. Relationships take work and then sometimes it doesn't work and then breakups suck. We imagine breakups probably suck extra hard when both people involved are famous; busy schedules, the pressures of being in the public eye, and just simple incompatibility mean celebrity breakups happen for a number of reasons, and sometimes it's not particularly anyone's fault, but it's still hard. 

Where things get especially interesting is when one person involved is a songwriter. There's a reason why the internet is full of breakup song playlists. Musicians process their emotions through their music, and sometimes fans are able to put lyrical puzzle pieces together and realize who a shady singer is singing about. As the queen of the post-breakup anthem Taylor Swift once said, "If guys don't want me to write bad songs about them, then they shouldn't do bad things."

In the seminal drag documentary "Paris is Burning," legendary queen Dorien Corey explains the concept of "shade" to the filmmakers. "Shade is, I don't tell you you're ugly. But I don't have to tell you, because you know you're ugly," she says. "That's shade." Along the same lines, songwriters fill their lyrics with references to their relationships, not usually outright saying who they're singing about — and they don't need to, because those people know. That's shade. Without further ado, here are shady songs musicians wrote about their ex.

The Dixie Chicks were on top of the world in the early 2000s until a political scandal derailed their careers: they dared to oppose the War in Iraq. A few years after the backlash, they had a relatively successful comeback single with "Not Ready to Make Nice," but after that, it would be fourteen long years, a divorce, and a name change before The Chicks released music again. Natalie Maines, one of the titular Chicks, went through a public breakup with her husband, "Heroes" star Adrian Pasdar, and the dissolution of their marriage formed the perfect basis for a barnstormer of a breakup album, "Gaslighter."

Fearing what Maines would say about him in song, Pasdar went to court to block the release of their unreleased music. The Blast reviewed Pasdar's court filings, which revealed that he was worried that their new music would violate the confidentiality clauses in their prenup. This was a surprise to Maines, because Pasdar had previously argued that he was under no financial obligation in the divorce because, he said, there was no prenup! 

Eventually, fans got to hear "Gaslighter," and the title track turned out to be one of the shadiest songs in recent memory. "Gaslighter, denier / Doin' anything to get your a** farther," they sang. "Gaslighter, big timer / Repeating all of the mistakes of your father." No wonder Pasdar didn't want the world to know how he'd treated her!

Taylor Swift could fill a list like this all on her own, but her ultimate shady song about an ex has to be her ten-minute epic, "All Too Well (10 Minute Version) (Taylor's Version)." As Swifties know, the song is about her fiery, three-month relationship with "Donnie Darko" star Jake Gyllenhaal. They dated from approximately October 2010 through January 2011, going on much-photographed walks and giggling over brunch together, but the relationship was not to last. However, it gave Swift plenty of material for her smash hit album "Red."

The re-recorded, expanded song came out in 2021, more than a decade after their breakup, and alongside a ten-minute short film re-enacting the relationship, the song itself featured new details for fans to pore over. Choice lyrics include "I'll get older, but your lovers stay my age." Ouch.

After years of shade from fans, Gyllenhaal addressed the backlash to his career sparked by the song in an interview with Esquire. The song's release led him to turn off his Instagram comments to avoid the wrath of the Swifties, and while he admitted he hasn't listened to the album, he expressed a wish that some of the "cyberbullying" would have been headed off by the singer. "At some point," he said, "I think it's important when supporters get unruly that we feel a responsibility to have them be civil and not allow for cyberbullying in one's name."

Abigail Breslin is primarily an actor, and an Oscar-nominated one at that; the pint-sized "Little Miss Sunshine" star received a nod when she was merely ten years old. Years later, she briefly dated Michael Clifford, the Australian lead guitarist of pop-punk band 5 Seconds of Summer. It was not meant to be.

Shortly after their relationship fizzled out, Breslin jumped into music with the release of "You Suck," a vicious track about all the things wrong with a former lover. "I'm laughing cause I lied, you know / I said you sound like All Time Low / You really don't, even though you try hard / You try hard," she sings over an infectious, if derivative guitar track. When the song was released, fans of 5SOS were unhappy. According to Genius, fans got #AbigailYouTried trending on twitter, and Clifford tweeted a string of reactions along the lines of "hahahahahahahaha."

He finally addressed the song a year later on the radio in Australia, protesting, "Literally we went to dinner one time and she... I can't, I can't!" The hosts tried to let him out of the awkward spot, and he demurred. "No, I feel bad, man. It's pretty awkward." Breslin later denied that she'd ever said the song was about him. "I learned that boy bands have a very, very strong avid following ... it got a little bit intense, some death threats," she told HuffPost Live (via Daily Mail).

Back at the height of the late 90s/early 00s teen-pop wave, Justin Timberlake and Britney Spears were the it couple, with the pop superstars turning heads whenever they showed up on a red carpet (who can forget their matching denim looks at the 2001 American Music Awards?). The N*SYNC breakout and the "...Baby One More Time" star were the envy of young people everywhere — until, abruptly, they broke up in early 2002. Timberlake went on the offense, telling People (via EW), "You get to a point where you're crying yourself to sleep at night."

Timberlake was also first out the gate to respond to the split in song, specifically in his hit solo single "Cry Me a River." The music video featured a Brit lookalike, which in combination with the song's lyrics heavily implied that Timberlake had been cheated on. "Girl, I refuse / You must have me confused with some other guy," Timberlake crooned. "The bridges were burned / Now it's your turn, to cry / Cry me a river."

Spears referenced the controversy almost two decades later in a good-natured caption on Instagram. She posed in a similar pageboy cap to the "Cry Me a River" stand-in, writing, "wait I look like that girl in the Justin Timberlake video with that hat in Cry Me A River !!! Oh s**t that's ME !!! I'm Britney Spears ??? I guess I forget that sometimes."

Carly Simon went a step further than the original definition of "shade" when she wrote "You're So Vain" about an ex. Whereas drag queen Dorien Corey says shade is when you don't have to tell someone they're ugly because they already know, Simon created a lyrical Catch-22: she did tell her ex that he's vain, but then she trapped the subject of the song into admitting it, because she knows he knows she knows. 

"You're so vain / you probably think this song is about you," she infamously sang. Though the song sparked much speculation about which of her famous exes she was writing about — a list of suspects that included James Taylor, Cat Stevens, Kris Kristofferson, and Warren Beatty — she refused to admit who she was shading for decades, letting them all believe they were the vain one she had trapped with her lyrics.

Decades after the song's debut, with the release of her memoir "Boys in the Trees," Simon finally admitted to People that the second verse of the song was indeed about Beatty, the infamous Hollywood lothario. "Warren thinks the whole thing is about him!" she joked. With those lyrics, how could he not?

The shadiest thing about Ariana Grande's post-Pete Davidson breakup song is that it isn't shady at all. GrandSon went their separate ways after a whirlwind romance that saw them meet, fall in love, get engaged, and have a falling-out all within the span of a few months in 2018, according to People. "It was way too much too soon," a source told the magazine.

Soon after their split, Davidson referenced the breakup on "SNL," jokingly proposing to musical guest Maggie Rogers mere weeks after ending things with Grande. Days after Davidson made that first public comment, Grande announced that her new single "thank u, next" would be out that very night. Fans assumed the song would be a telling-off to her famous ex, but whereas the title sounds like it's going to be an angry rebuke to a past lover, the song is complimentary of all of her former flames. 

Lyrics like "Even almost got married / And for Pete, I'm so thankful," indicated that she appreciated their time together anyway; the song is instead about learning and growing from each person who breaks your heart. Whereas fans expected shade, the song instead suggests that the tiny popstar is the bigger person, leaving her exes no opportunity but to mature with her or else look bad. "I've got so much love / Got so much patience / I've learned from the pain / I turned out amazing," she sang.

It may seem strange now, but when Katy Perry first hit the scene, she was considered more pop-punk than pop. She was even part of the 2008 lineup of Warped Tour, traveling the country alongside bands like All Time Low, Cobra Starship, and Gym Class Heroes. The latter band was fronted by Travie McCoy, Perry's boyfriend at the time. The relationship was apparently serious enough that McCoy bought Perry a promise ring, confessing to People that he was "so scared to give it to her."

According to People, the two broke up the following year. McCoy posted song lyrics on his blog about the breakup (ah, 2009!), quoting from Main Source's "Looking at the Front Door." He wrote, "We fight every night, now that's not kosher / I reminisce with bliss of when we was closer." Perry, though, wrote her own song. "Circle the Drain," from her album "Teenage Dream," is a kiss-off song about McCoy and addiction. "Wanna be your lover, not your f***in' mother," she sang, shading him for falling asleep during foreplay. Oof!

McCoy clapped back to MTV about the song, throwing his own shade in return. "I heard she put out a song that's about me, or about some old habits," he said. "I look at it like this: I'm just stoked that she finally has a song with some substance on her record. Good job."

For a while in the early 2010s, two of the biggest groups in the world were joined by romance. One Direction's Zayn Malik dated Perrie Edwards from Little Mix for four years, no doubt exciting "The X Factor"'s Simon Cowell about the possibilities of a next-generation boy and girl band someday. Malik even got a tattoo of Edwards' face. "She loves it, she thinks it's good," Malik told CapitalFM. However, even though they got engaged, wedding bells were not in the cards. According to Edwards in the Little Mix book "Our World" (via E!), Malik dumped her ungraciously. "A four-year relationship, two-year engagement ended by a simple text message," Edwards wrote.

Thankfully, she turned the pain into the absolute dancefloor-storming banger that is "Shout Out To My Ex," the lead single from LM's album "Glory Days." Edwards starts the song; in addition to lyrics referencing the length of their relationship and a certain tattoo she felt expected to be grateful for — cluing fans into who the song was about — she sings, "Forget that boy, I'm over it /I hope she gettin' better sex / Hope she ain't fakin' it like I did, babe." That about says it all.

"I love that song, and I never get tired of singing it," Edwards told CapitalFM years later. We can see why!

P!nk met her husband Carey Hart all the way back in 2001 at the X Games, where the motocross racer was competing. They married in 2006. However, by early 2008, P!nk announced on her website (via MTV) that they had split up. "The most important thing for you all to know is that Carey and I love each other so so much. This breakup is not about cheating, anger, or fighting," she claimed.

Later that year, gearing up for the release of her circus-themed album "Funhouse," P!nk unveiled the first single, "So What," a carefree anthem that spoke to how little she was bothered by her impending divorce from her tatted beau. "I guess I just lost my husband / I don't know where he went," the song begins before the singer insists that she doesn't need him anyway. "So what? / I'm still a rockstar." She later described the song to The Guardian as a "vomiting of truths."

Behind the scenes, though, it seems that the song might have just been some shady posturing. P!nk later told Redbook that she won Hart back by presenting him with a scrapbook of every card he'd ever given her, and the two had successfully reconciled by the time the song's music video was released. Hart even plays himself in the video, lampooning their fighting. They have been together ever since.

Justin Bieber and Selena Gomez were, at one point, the 2010s' answer to Britney Spears and Justin Timberlake. Two mega-famous teen stars had found one another and fallen in love amid the craziness of Hollywood, and though they broke up and got back together a number of times over the years, fans always hoped they'd be able to work things out. During one of their breaks, one that seemed like it might be final, Bieber released "Purpose," an album filled with tracks widely-interpreted to be about the former Disney actor.

The shadiest of the lot is "Love Yourself," which sounds from its title like it should be an inspiring self-love anthem. Instead, has lines like "My mama don't like you, and she likes everyone." When he tells the subject of the song, "You should go and love yourself," it sounds like maybe he means to use another four-letter word instead.

Bieber told Access Hollywood, "[She] is someone I love dearly," he said. "I'm never going to stop loving her. I'm never going to stop checking in on her." According to Elle, they were back on several months after the release of the album. Apparently it wasn't too late to say sorry!

Though Justin Bieber was the first to define a Jelena breakup narrative with his album "Purpose," released amid a split from on-again, off-again paramour Selena Gomez, they got back together. E! reported that they broke up for the last time in 2018, and Gomez took her time crafting her own sonic response. 

Two years later, Gomez proved she'd grown from the way she'd been treated, writing one of the shadiest things you can say to an ex, especially once they've already made themselves look bitter with a song like "Love Yourself." On her single "Lose You to Love Me," she showed what needed to happen to follow his advice. She sang, "We'd always go into it blindly / I needed to lose you to find me / This dancing was killing me softly / I needed to hate you to love me."

As if there was any doubt who the song was about, Gomez seemingly confirmed it was about Bieber in an interview with Ryan Seacrest. Fans had picked up on the song's lyrics about moving on quickly — "In two months, you replaced us" — because by the time the song was out, Bieber had already quickly married model Hailey Baldwin. "It's all very real to me and I'm sure it's just entertainment for other people," Gomez said, "but I think I had become numb to it and it would be stupid of me if I didn't acknowledge what I had felt."

After six months of dating, "Glee" star Naya Rivera got engaged to "Dance (A$$)" rapper Big Sean in late 2013, according to JustJared. He told E!, "Every morning I wake up, I look over to her, and be like, I'm winning so hard."

However, in her memoir "Sorry, Not Sorry," Rivera revealed that she found Sean to be "incredibly selfish;" they didn't wed. Per Vulture, she recalled telling him that her "Glee" co-star Cory Monteith had died. "I was crying and kept coming in and out of the room as I went out into the hallway to make phone calls, and he never got out of bed or even so much as sat up and turned on the light," Rivera wrote. "This still blows my mind to this day." 

After they split, Big Sean released "I Don't F*** With You," or "IDFWU" for short. The song is a brutal reminder to an ex that no matter how upset they may expect you to be about a breakup, you just don't care. "I don't f*** wit' you / You lil' stupid a** b***h / I ain't f***in' wit'chu," he raps. In an interview with Complex, the rapper denied it was about Rivera, but he also claimed that it was written because "I just dodged a bullet from a crazy bi***" mere months after calling off their engagement. Rivera later performed the song on "Lip Sync Battle," showing that she, too, was over it.

Miley Cyrus and Nick Jonas were yet another couple of famous teens who fell in love, though they hid their relationship from fans until years after they broke up. According to Cyrus (via Seventeen), "For two years he was basically my 24/7. But it was really hard to keep it from people." 

She wrote her hit "7 Things" about Jonas, though she didn't admit the inspiration until years later. The song is a shady rundown of all the things she hates about her ex love, including such deal-breakers as "you're vain, your games, you're insecure." Eventually, though, it shifts into a list of all of the things she loves, too; fitting, because the two have remained great friends over the years. Celebrating the song's anniversary on Instagram, Cyrus tagged Jonas and shared a quote from her memoir reminding fans of her mindset when she wrote the jam. "I was angry when I wrote '7 Things,'" Cyrus reflected. "I wanted to punish him, to get back at him for hurting me."

Jonas said that Cyrus never told him directly that the song is about him, but because of Miley's choice of jewelry in the music video, he's been able to put the pieces together. "She's wearing a dog tag in this [music video] that I gave her when I was 14 or something," Jonas revealed in an interview on BBC Radio 1. "I was actually kind of flattered, to be honest."

Alanis Morissette's album "Jagged Little Pill" is the quintessential breakup album; Dig called it "the breakup album to end all breakup albums." The lyrics on the album are full of imagery so vivid and emotions so strong that they have even formed the basis for a hit Broadway musical written by Diablo Cody, so it makes sense that fans of the Canadian rocker have spent decades poring over the songs in an attempt to figure out who they're about.

One particular ex-boyfriend recognized himself in Morissette's lyrics. "Full House" star Dave Coulier revealed in 2013 that he suspects "You Oughta Know" is about him. The song features lines about an ex's new woman, finding the singer wondering things like "Is she perverted like me?" The first verse ends with the ultimate shade, especially if you want your ex to remember how fun and exciting your relationship used to be: "I'm sure she'd make a really excellent mother."

Coulier specifically copped to seeing himself in the second verse, where Morissette sings, "I hate to bug you in the middle of dinner / It was a slap in the face how quickly I was replaced." Coulier told HuffPost Live (via Business Insider), "We had already broken up... She called and I said, 'Hey, you know, I'm right in the middle of dinner. Can I just call you right back?' When I heard the line, it was like, 'uh-oh.'"