Famous Breakup Songs Inspired by Other Celebrities

Demi Lovato was only 17 when she started dating then-29-year-old Wilmer Valderrama back in 2010. Recorded when she herself was 29, this Holy Fvck track points out how questionable their relationship was based on the dramatic age difference. 

“Thought it was a teenage dream, just a fantasy / But was it yours or was it mine,” they ask on the anthemic chorus. Lovato even calls out their ex for a string of younger partners, which includes the actor’s current fiancée Amanda Pacheco.

“‘29’ is a record about the wisdom that comes with age,’” Lovato wrote on Twitter, again highlighting how inappropriate she finds the relationship now that it’s in the rearview mirror.

Britney Spears and Justin Timberlake were bubblegum pop royalty in the early ‘00s, which made their 2002 breakup international news. Things took a turn for the dramatic when Timberlake dropped “Cry Me A River,” which strongly alluded to infidelity in their relationship. 

“You were my sun, you were my earth / But you didn’t know all the ways I love you, no / So you took a chance and made other plans / But I bet you didn’t think that they would come crashing down,” he rages over R&B production courtesy of Timbaland. 

The accompanying music video even features a Spears look-alike, giving the allegedly jilted lover a chance to get revenge. At the time, the track propelled Timberlake’s then-nascent solo career into the stratosphere.

“Cry Me a River” — according to some, the first of several breakup tracks about Britney Spears — highlighted the anger Justin Timberlake felt after they went their separate ways. Spears charted a different path with her tender ballad “Everytime.” 

Instead of raging and burning down the love they once shared, she apologized for anything that might have pushed them off the rails. “I may have made it rain / Please forgive me / My weakness caused you pain / And this song’s my sorry,” she coos as the song reaches an emotional crescendo. 

Years later, “Everytime” remains the hit-maker’s most recognizable ballad. It also introduced an entire generation to the wrong spelling of “every time.” 

Following the doomed love of Britney Spears and Justin Timberlake, Justin Bieber and Selena Gomez became the reigning teen royals of the 2010s. Their on-and-off relationship continued over the decade  before they ultimately went their separate ways, with Bieber marrying Hailey Bieber (née Baldwin) in 2018. 

Along the way, Gomez opened up about her feelings in song. Her most recent ode to the relationship — 2019’s  “Lose You to Love Me” — might be her last; it allowed her the space to let go of the past and move onward and upward in her journey to self-love. 

“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,” she admits over a sparse production. Gomez turns the page to a new beginning in the ballad’s final lines. 

It’s rare to find a breakup song so beloved that fans clamor to listen to a 10-minute version years after its initial release. However, that was the case when Taylor Swift revisited “All Too Well” on 2021’s Red: Taylor’s Version. Nearly a decade after it initially arrived, she expanded upon what many believe is a tribute to her relationship with Jake Gyllenhaal. 

Swift continually proves herself to be the queen of Easter eggs: She slyly hints at the meaning behind her songs by littering them with referential lines and injects meaning into the smallest details. Meanwhile, her fans deserve medals for how religiously they translate her symbolism and present it to the rest of the world. That’s exactly what they did with “All Too Well.” 

Details such as a scarf left at the home of her ex’s sister — presumably Maggie Gyllenhaal — give them confidence in saying the song is about Gyllenhaal. For what it’s worth, he denied the rumor in an interview with Esquire. However, Swift will never confirm, which only adds to the intrigue. 

Here’s another example of Taylor Swift’s ability to subtly allude to former romances in song. Although it hasn’t been confirmed in as many words, fans believe 1989’s “Out of the Woods” is about Harry Styles.

There’s multiple lyrics that hint at their relationship, including a reference to a paper airplane necklace Styles gave her when they were together. (Swift even cleverly compared the couple to “paper airplanes flying” shortly after singing about the piece of jewelry.)

The lyrics also reference an accident that left her and a beau in the hospital. Again, while not officially confirmed, it’s believed Styles was her boyfriend when they were involved in a snowmobile accident that was kept from the press.

It’s a bit of a guessing game, but this one feels like a safe bet!

Ariana Grande proved herself to be the ultimate multi-tasker when she unleashed “thank u, next” in 2018. After calling off her brief engagement to Pete Davidson, Grande paid tribute to all of her famous exes in one song. 

“One taught me love / One taught me patience / One taught me pain / Now, I’m so amazing,” she sings on the bouncy, upbeat anthem. Davidson, Mac Miller, Big Sean and Ricky Alvarez are all individually name-dropped in the lyrics before the pop star celebrates her latest relationship: the one with herself. 

Paired with a music video that references some beloved rom-coms from the early 2000s, “thank u, next” elevated Grande’s star power to another level. It also became her first song to top the Billboard Hot 100, all thanks to the enduring power of lost love.

Halsey and G-Eazy compared themselves to Bonnie and Clyde on 2017’s “Him & I,” even though they burned out in a totally different manner than the legendary bandits. On the loved-up track, G-Eazy raps that Halsey would “try to cut” an intimate body part off if he ever cheated. 

The following year, Halsey accused him of just that on the chart-topping “Without Me.” The anthemic single finds Halsey singing about a relationship in which she gave her all but consistently got burned. The song also references another track on this list: “Cry Me a River.” 

“You don’t have to say just what you did / I already know / I had to go and find out from them,” they sing on the bridge.

Miley Cyrus and Liam Hemsworth seemed like they were meant to go the distance when they reunited in 2017 after calling off their 2012 engagement. They were married in 2018 but called off the marriage the following year. That’s when Cyrus dropped “Slide Away,” a mournful but resolute ode to moving on and making her own decisions. 

“Once upon a time it was paradise / Once upon a time I was paralyzed / Think I’m gonna miss these harbor lights / But it’s time to let it go,” Cyrus sings, alluding to her partner returning to Australia while she explores the lights of the city. 

“Move on, we’re not 17 / I’m not who I used to be / You say that everything changed / You’re right, we’re grown now,” she adds on the outro, effectively paving the way for a new beginning without her ex, who she started dating when she was — you guessed it — 17. 

They never made it down the aisle, but Nick Jonas apparently heard wedding bells when he first saw ex Miley Cyrus. The Disney stars dated as teens for a couple of months before going their separate ways. After the split, Cyrus famously wrote “7 Things” about Jonas.

While his song “Wedding Bells” didn’t make it onto an official album, it was included on 2013’s LiVe following a failed band reunion. At the time, it was clear to fans that the song was a reference to Jonas and Cyrus’ young love — the lyrics even refer to the day they met. 

“No I don’t wanna love / If it’s not you / I don’t wanna hear the wedding bells prove / That we can’t try / One last time / But I don’t wanna hear the wedding bells chime,” he sings on the moody, midtempo number. Considering the timing, it seems like the track could have been a reference to Cyrus’ then-fresh engagement to Liam Hemsworth.

Katy Perry has been in multiple famous relationships, but it was a total surprise when she revealed the man who inspired “The One That Got Away.” While filming Witness World Wide in 2017, Perry told James Corden that Josh Groban was the one she never had a chance with.

“No, he’s not in there. But I do want to say, people are like, who is ‘The One That Got Away’ about? That’s Groban,” Perry said when asked to rank her exes in bed, making her 2010 breakup anthem all the more unexpected. 

“In another life, I would be your girl / We’d keep all our promises, be us against the world / In another life, I would make you stay / So I don’t have to say you were the one that got away,” she sings on the effervescent and earnest chorus. 

Perry has since moved on with Orlando Bloom. However, she and Groban are still friends today!

While Katy Perry sang about Josh Groban, her ex John Mayer confirmed to The New York Times that his song “Still Feel Like Your Man” is about the pop star.  Two years after they went their separate ways for good, Mayer yearned for another shot with the hit-maker on the breezy track.  

“I still keep your shampoo in my shower / In case you wanna wash your hair / And I know that you probably found yourself some more somewhere / But I do not really care / ‘Cause as long as it is there / I still feel like your man,” he admits on the song. 

Jessica Simpson was all blissed out on Nick Lachey when she released “With You” in 2003. The song signified the start of their life as husband and wife and helped push them to the forefront of pop culture. Just a couple of years later, they closed that chapter, and Lachey opened up about the divorce on his track “What’s Left of Me.” 

“I don’t wanna waste another day / Stuck in the shadow of my mistake / ‘Cause I want you, and I feel you / Crawling underneath my skin / Like a hunger, like a burning / To find a place I’ve never been / Now I’m broken, and I’m fading / I’m half the man I thought I would be / But you have what’s left of me,” Lachey sings on the heartwrenching pop ballad.

Both have since moved on and found happiness in other relationships.

Gwen Stefani shook off the shock of her divorce from ex-husband Gavin Rossdale on 2015’s “Used to Love You.” Co-written with Julia Michaels and Justin Tranter, the track highlights her resolve and celebrates memories of happier times with her ex. 

“Never thought this would happen / Gotta let it sink in, you’re gone,” she sings on the opening lines, before releasing some of her anger on the chorus and hinting at the conflicted feelings that one can face while going through a divorce. 

“I don’t know why I cry / But I think it’s ‘cause I remembered for the first time / Since I hated you / That I used to love you,” Stefani sings. 

Olivia Rodrigo rocketed from rising Disney star to global phenomenon when she unleashed “drivers license” in the midst of the pandemic in 2021. The breakup track finds her singing about a relationship that fizzled when her ex moved on and left her behind with nothing but memories. 

“Red lights, stop signs / I still see your face in the white cars, front yards / Can’t drive past the places we used to go / ‘Cause I still f—ing love you, babe,” she sings on the momentous bridge. 

Her youthful mourning sparked rumors of a love triangle involving her High School Musical: The Musical: The Series co-star Joshua Bassett and Sabrina Carpenter. Adding to the allure, Carpenter (believed to be the older blonde girl referenced in Rodrigo’s song) dropped a track of her own called “Skin” that many believed was in response.