We may not know celebrities personally, but it's easy to get wrapped up in their lives. We start to follow their drama compulsively and live vicariously through whatever our fave celeb may be doing at the time. This includes relationships. It's so easy to get way too into celebrity couples! We want the best for our idols and watching them be in loving, fulfilling relationships is always amazing. But, inevitably, we have to deal with tragic celebrity breakups. The kind we shouldn't care about (because, again, we don't know these people) but can't help obsessing over!
In the last 30 years, some classic Hollywood pairs have gone their separate ways after what we assumed would be ~forever~. Celebrity breakups sometimes feel personal, like your BFF is ending things with her longtime love. Especially when you've watched their romance unfold over social media, tabloid pages, and sometimes even TV! But, all good things must come to an end. (But, like, why? What a terrible expression!). Here are all the tragic celebrity breakups from the last 30 years that made us stop believing in love!
These two rising stars were the "it" couple of the late '90s and early '00s. The two met at Witherspoon's 21st birthday party in 1997 and by 1999, the two were married with a baby on the way. But, in 2006 it was all over. We were devastated by two of our fave actors splitting (and denying us another on-screen collaboration like Cruel Intentions!). Apparently, Phillippe was flirting with other women and may have even cheated. So, not only did these two split but one of Hollywood's leading hotties may be trash! While the breakup was sad, there was at least one thing from this relationship we'll always have: Ava Phillippe a.k.a Reese Witherspoon 2.0!
Leoni and Duchovny began dating and got married in a span of eight weeks in 1997! It's easy to think, based on their short courtship, that this relationship wouldn't work out. The two defied the odds, though, and stayed together year after year. So, it was even more devastating when they split for good in 2014 after 17 years together. We totally thought these two were the poster children for "when you know, you know" type of love stories. Fortunately, the two shared many happy years and two daughters together during their relationships so it wasn't all for nothing. Despite their eventual split, it's still nice to know that marrying someone after knowing them only a short time isn't always the cardinal sin of Hollywood dating!
Together, these two built an empire. In the wake of Kris's split with first husband Robert Kardashian, she met and married a hunky Olympian. The rest is E! history as we've kept up with them for over a decade! The two have become more than just Calabasas royalty — they've created the Kardashian-Jenner dynasty that is basically the closest thing we have to royals in America. But, even royalty isn't immune to turmoil. After 22 years of marriage, the two separated in 2013 and were formally divorced by 2015. Many speculated that the split was because of Caitlyn coming out as transgender and her eventual transition to her true gender, while other reports say that Kris treated Cait horribly and the split was a long time coming. No matter the cause, it's always sad when a decades-long relationship ends!
These two theater stars have one of the most epic romances on all of Broadway. They met during the original production of Rent in 1996 and began a relationship from there. The two were married in 2003, welcomed a son in 2009, but, by 2013 they were done. The theater community was shook that their fave couple was splitting! They never gave a reason for the split, but it was hard to imagine the King and Queen of Broadway not being together. The pair continues to be friends and co-parents to their son. But, while we love friendly exes, we can't deny that we wish these two gorgeous theater geeks were still together!
These two were one of the hottest couples in Hollywood for a bit. In 2007, the gorgeous couple got together and seemed to be the type of pairing dreams are made of. It was pretty heartbreaking when the two split in 2013, one of the worst years for romance. If these two beautiful people can't make it work, who can?! On the upside, they have truly taught us what it's like to be mature adults after a relationship ends. They've continued to be friends, co-parent wonderfully, and always talk each other up in interviews. A romantic relationship between the two just wasn't meant to be! They've both moved on since, and if Bloom and Katy Perry ever split, we'll have another addition to this list!
It's always amazing when two artists at the top of their game get together and rule the scene. Shelton and Lambert were THE reigning couple of country music for almost a decade after they started dating in 2006. Their 2015 split took country fans and haters alike by surprise because the two always seemed so in love. They were always busting on each other in interviews and giving us normal people hope that long-distance love could actually succeed. Even more tragic is the fact that they have both accused the other of infidelity, ending their seemingly perfect marriage on a super sour note.
RCA/Village Roadshow Pictures
Remember a simpler time when Duhamel was on TV every week and The Black Eyed Peas' songs were all over the radio? It was at that time, in 2004, that Duhamel and Fergie met when her band guest-starred on his TV show Las Vegas. The two were married five years later in one of the more unlikely, but adorable, pairings in Hollywood. They also ended up being one of the most unlikely celebrity breakups in 2017 when they announced their split. Apparently, the two were just too different to make it work. So sad that after all that time together, they just couldn't make their lifestyles mesh!
These two may have been short-lived, but they were adorable AF. The two were together from around 2005 until 2006 and they were both at the height of their fame. Moore was churning out pop hits and Braff was starring on Scrubs. They seemed so perfect together but their brief romance came to end almost as soon as it started. In the aftermath, Moore said that their breakup exacerbated her depression (though, she makes clear it wasn't the main reason for it). Braff has said that he didn't like dating Moore due to the intense microscope they were under as one of the most famous couples in Hollywood. We're guessing those things were likely factors in their split.
Element Films/Marc Platt Productions
These two were a bona fide Hollywood power couple throughout the '90s. They got married in 1987 and stayed together until their divorce was finalized in 2000. Their relationship was one of the longest celeb couplings in recent history so their split was extra disheartening. If these two crazy kids couldn't make it after almost 15 years together, no one can! While a romantic relationship didn't work out for them, they have shown the world how to be the friendliest exes on the face of the planet. Willis was even pals with Moore's next husband, Ashton Kutcher, and they all hung out together! Their support of one another post-divorce makes this split a little less painful.
Seal has sung more than a few panty-dropping romance ballads so we kind of assumed these two had a pretty passionate marriage. The two were married in 2004, and reportedly they renewed their vows on their anniversary every single year with their family and friends. That's how into each other they were! But, there was clearly trouble in paradise because one of the most tragic celebrity breakups of all time happened in 2012 when these two called it quits. The only reason they gave was that they had grown apart and that their highest priority was their four children.
Warner Bros. Pictures/NBC
After meeting on the set of Gaga's video for "You & I," these two were one of the cutest couples in Hollywood. Gaga has always been a little out there and it seemed that she found someone completely accepting of all her quirks. That's all fans ever wanted for our Mother Monster! The pair dated for four years before getting engaged in 2015 with a giant heart-shaped diamond ring. But, in 2016 they called it quits and Gaga said it was her career that got in the way. Tragically, she reported in her documentary Five Foot Two that when her career is going great her, love life always seems to implode. Balancing her massive career and the men in her life just never seem to line up. So sad!
Bless our teen hearts. At a certain moment in time, these two were all anyone could talk about. Two of the hottest teen sensations in the world dating was major. They broke up and reconciled more times that we can count, giving us the hope that they were meant to be. But, alas, they weren't. They broke up for the final time in 2017 and Bieber is now married to Hailey Baldwin (a.k.a Hailey Bieber!). Fans of Selena and Justin's romance were devastated that their fave power couple was officially done for good. First loves are always hard to let go of, which is why we're still not over this celebrity breakup!
Fox Searchlight Pictures/AMC
Before Hamm was Don Draper on Mad Men and constantly going out in public without underwear (one word: wow), he was just another struggling actor. By his side during this time, and through his meteoric rise, was his girlfriend Jennifer Westfeldt. The fact that she had been with him since the beginning made us think this love story would go on forever. So their split in 2015, after 18 years together, was heartbreaking. Celebrity breakups are usually a dime a dozen but it seems to hit harder when a couple has been together for so long!
Stefani and Rossdale were the '90s rock couple of our dreams. The No Doubt frontwoman and Bush singer met in 1995 at a holiday concert for a radio station and were inseparable from there. They were the too-cool couple that everyone wished they could be like. Even as they had kids, they just had effortless rocker attitudes that made us love their relationship. But, in 2015, their relationship ended when Stefani filed for divorce. The real shocker: Rossdale had reportedly been cheating for three years with the family nanny! Stefani wrote some truly soul-baring songs about the end of the relationship and we all cried along with her. Luckily, she's found love with another celeb on this list: Blake Shelton!
These two were the epitome of opposites attract when they began dating in 2000. Madonna is a controversial pop songstress whereas Ritchie is embroiled in the world of filmmaking (peep his work with 2019's live-action Aladdin remake!). But, they made it work and adorably started a family that consisted of a biological son and an adopted Malawian child. When they split in 2008, the world was stunned, but it's the details of the split that are extra tragic. Reportedly, their split came on the heels of Madonna being too career oriented and Ritchie not wanting to be "Mr. Madonna" anymore. They just couldn't make the balance between family time and career aspirations work and it led to the end of their eight-year romance.
The CW/Regency Enterprises
We were devastated when Bilson and Adam Brody broke up, but her split with Christensen was even worse. The two quietly began dating in 2008 after Bilson split with her The O.C. co-star. Her new romance was perfectly low-key couple and the two seemed to be truly happy together despite a brief relationship hiatus. They even welcomed a baby girl in 2014! But, by 2017, their nomadic lifestyles as actors was coming between them and they ended things. They may have had one of the more quiet celebrity breakups but that doesn't mean it wasn't sad to see the almost decades-long relationship come to an end!
Walt Disney Pictures/Showtime
These two were one of those Hollywood couples. They were together for years, never got married, but you knew you could rely on their love to hold strong. That was until 2016 when, after ten years together, they broke up and proved true love was dead. The two were always a reliably fun red carpet couple and they clearly had tons of love for each other. Plus, watching Pacey Witter's heart get broken is as devastating in real-life as it was on Dawson's Creek!
Cox and Arquette were a hilarious dream-team of a couple during the height of their careers in the late '90s. They were two of the funniest rising stars in Hollywood so their relationship just made sense. Sadly, after over a decade together, they called in quits in 2010. Even sadder was Arquette's post-split assertions that he was begging Cox to take him back and that she may have grown tired of his immature ways. He also noted that they still loved each other immensely but wasn't sure that just love alone meant you should be with someone for the rest of your life. Always unfortunate when two people who clearly love each other can't make it work!
Another of one Hollywood's most adorable long-term couples that never married! They were together for over a decade and, despite the fact that they never traveled down the aisle, we just couldn't imagine them breaking up. In 2016, though, they announced their split and one of the most stable couples in Tinseltown was no longer. Schreiber gave an interview after the split where he said he hated not living under the same roof with his entire family anymore. Watts echoed the sentiments and said they were all just trying to navigate this new part of their lives as best as they could.
New Line Cinema/HBO
Aniston was perpetually considered one of those women in Hollywood who was unlucky in love (as if being lucky in love is some defining trait). After her tumultuous split from Brad Pitt, the big question was will Jen ever find love again? Ignoring the fact that a woman is so much more than whatever man she's with, Jen did find love again. This time it was with smart, funny, and downright gorgeous actor Justin Theroux. Watching our fave friend and Theroux build a life just made us happy. So, when the two split in 2017, it was tragic for a few reasons. Obviously because their love story came to an end, but also because we're going to have to endure the "Jen Aniston spinster" articles for a while now. TBH, we're over that narrative.
These two went through so much together. After they began dating in 1989, they spent over 20 years in each other's company. Sure, there were plenty of breakups and makeups in those years but these two always worked it out. They even filed for divorce in 2007 but ended up withdrawing the petition and getting back together! Unfortunately, their rollercoaster love store came to an end for real in 2010 when they officially divorced. We thought Penn and Wright could make it through anything! Unfortunately, not everything is so easy to navigate through.
The CW/The CW
This relationship is what shipper dreams are made of. The two began dating after meeting on the set of The Vampire Diaries and fans went wild for their romance. Their characters, Elena and Damon, were so many people's OTP that the idea that they were together in real life was almost too much to handle. Plus, have you seen these two?! They made up one of Hollywood's sexiest couples of all time. Their eventual split was devastating for fans of The Vampire Diaries, but as far as celebrity breakups go these, two did it so right. They remained friends, continued working together on the show, and Dobrev is even friends with Somerhalder's now-wife, Nikki Reed!
Who would have thought that a couple who wore matching denim outfits would someday break up?! We are still not over this tragic celebrity breakup. Timberlake and Spears were the pop music King and Queen during their three-year relationship. It seemed almost too perfect that these adorable, blonde sugary-sweet pop musicians found love with each other. But we accepted it and loved every minute of their budding romance. When they split it was literally the end of an era. Soon JT went solo (and released "Cry Me a River" all about Brit-Brit) and the age of boy bands and midriff-baring pop sensations was over.
Olive Bridge Entertainment/Relativity Media
Stone and Garfield went from co-stars to lovers after filming The Amazing Spider-Man in 2011. While both are pretty private about their personal lives, they were quite inviting into their romance. They bantered during interviews and canoodled on red carpets, proving they were cute with a capital "C." Stone even dropped by when Garfield hosted Saturday Night Live to give him an adorable boost! But it all came to an end in 2015 when they two broke up. While that was sad, the two have not stopped gushing about each other in the press since their split. Here's to hoping these crazy kids can find their way back to each other!
Longtime J.Lo fans just want our girl to be happy. It seemed that she had finally found lasting love and happiness with Marc Anthony when their whirlwind 2004 romance ended in a marriage that same year. They were both of Puerto Rican heritage and had the same values and traditions. They even had twins in 2008, beginning an adorable little family. It finally seemed like Jennifer had found her perfect match! All of our hearts broke for the couple when they announced their separation in 2011. By 2014, their divorce was finalized and the two moved on with their lives. This was Jenn's third divorce and, TBH, our girl deserves a forever kind of love. Luckily, it seems like she may have found it with Alex Rodriguez.
NBC/Laurence Mark Productions
These two met on the set of High School Musical and became every tween's idea of #relationshipgoals. The beautiful up-and-coming actors were a perfect pair from 2005 until 2010. Their split was basically devastating for anyone ages 9-16. Troy and Gabriella forever! Looking back, it's clear they were each other's first love but grew out of the relationship. Sure, we're happy that they've gone on to find happiness in their adult lives. But we're still waiting for High School Musical 4 and a reunion for these two!
Bleecker Street/Skydance Media
Who can forget Cruise jumping on that couch and professing his undying love for Katie Holmes? Sure, he's a little weird and their relationship wasn't perfect. But he was so beyond happy to be with her that it felt like a perfect match! They were engaged within weeks of their first date and on the one-year anniversary of that date their daughter, Suri, was born. Then, just like that, they were over. They were married for almost six years before Holmes filed for divorce. The divorce was settled within ten days and Holmes received full custody of Suri. The sad part is how they went from blissfully happy to Holmes reportedly being scared for the wellbeing of her daughter due to Cruise's involvement with Scientology. Reportedly, Cruise hasn't seen Suri in years and part of the filings said Katie couldn't go public with another relationship. That poor little girl!
Instagram/@giseleVillage Roadshow Pictures
Before she was Mrs. Tom Brady (the GOAT!), Gisele was part of one of the hottest couples to ever grace Hollywood. The beautiful pair were together from 2000 until 2005, making it one of DiCaprio's longest relationships. He's usually hopping from one model to the next! But he and Gisele were the real deal for a while until the two headed towards splitsville. In a 2019 interview, Gisele revealed that she was sick of partying and Leo wasn't so they needed to go their separate ways. We'll never stop wondering what their kids would have looked like, though!
Hurley and Grant certainly had their drama, but they were supportive of each other through everything. They met when Hurley was just starting out in 1987 and Grant helped her achieve her career goals. On the opposite end of the spectrum, Hurley supported her man when he was outed for soliciting a sex worker in 1995. Throughout their 13-year relationship, they were forgiving, loving, and there for one another through everything. The two amicably split in 2000 and the good news is is that they've remained BFFs ever since!
Regency Enterprises/Village Roadshow Pictures
This is one of the most shocking celebrity breakups of all time. Not only for its suddenness, but also for the alleged contention and controversy surrounding the split. Pitt and Jolie were one of the most private A-list couples in the world but they seemed genuinely happy together. After meeting on Mr. & Mrs. Smith, the two fell in love and started a life together (while Brad was still with Jen, but still). "Brangelina" spent 12 wonderful years together until they abruptly split in 2016. Jolie was seeking full custody of the kids and was reportedly refusing to speak to Brad after some sketchy stuff happened on a private jet. Eventually, he was investigated for child abuse due to the incident and cleared. It was all dramatic and toxic, something fans had never thought would come from this gorg couple.
This technically shouldn't be on a list of celebrity breakups. You know, since instead of breaking up, they "consciously uncoupled." After a decade of marriage, these two split for good in 2014. They were a pretty private couple but were the poster children for actor-musician relationships — they also named their kid Apple, which gained them a fair bit of attention as a couple. It truly does seem as though their breakup was about as amicable as you could hope for. They said their relationship wasn't the same as it used to be and they "uncoupled" while still committing to their family and friendship. It almost makes us love them even more, even if their strange breakup language was a sign of the "Goop" pretention that was to come!
FX/Castle Rock Entertainment
This is one of the most devastating celebrity breakups merely because of how long these two were together! Robbins and Sarandon were together for 23 years before they called it quits in 2009. The two met on the set of Bull Durham and began a relationship that spanned decades. They were one of the most reliable couples in Hollywood — if they can't make it, who the heck can?! The famous couple never married because, as Sarandon put it, she didn't want them to take each other for granted. They still managed to build a life and a family over the two decades their romance and careers ruled Hollywood.
Village Roadshow Pictures/DreamWorks Pictures
The couple that makes movies together stays together! Well, maybe not. Taylor and Stiller were the first couple of comedy from 2000 until 2017. Not only were they adorable together in real life, but they were incredible together in the many movies they collaborated on. From Dodgeball to Zoolander, these two were amazing on and off-screen. In 2017, they ended their personal and professional collabs and announced their separation. They still aren't officially divorced — and have been spotted hanging out! — so maybe this tragic breakup will lead to a makeup!
UK Film Council/YouTube
There's a reason Bonham Carter is always in Burton's films — the two were together for 14 years! In that time, Burton cast her in tons of his movies and the two made magic together on-screen and off. They even have two children together and we bet they're just as off-beat as their parents! These two just made so much sense together. They have the same weird sense of humor and a dark, mysterious vibe. There's a reason she fits in so perfectly in his films! So it was pretty upsetting when they announced their split in 2014. The unconventional couple never married or even lived together (they lived in adjoining houses!) but that was the beauty of their love. They defied odds and showed that any type of alternative relationship could succeed. This made it all the more devastating when they called it quits!
It's always tragic when two people who seem so perfect together call it quits! The two comedians married in 2003 and appeared in several movies and television shows together during their years as a couple. They also welcomed two sons, one in 2008 and one in 2010, over the course of their marriage. It was shocking when the funny couple announced their separation in 2012. It wasn't until 2016 that the divorce was finalized but the two were definitely over during that time. So, basically, our hearts just kept breaking as they dragged out their split and subsequent divorce!
Grand Via/Summit Entertainment
After co-starring in The Notebook (a.k.a the most romantic movie of all time), these two fell in love off-screen. It's shocking, though, considering Gosling reported the two had a combative relationship on-set. Though, let's be real, that report makes us think these two are even more like Noah and Allie! They were the sexiest couple in Hollywood from 2005 until 2007, even accepting a "Best Kiss" award in the steamiest way possible! It's celebrity breakups like these that make us stop believing in love, TBH. The two split in 2007 and went their separate ways. We'd be lying if we said we aren't waiting for them to reunite when they're a little bit older, just like their characters in the film! But Ryan's relaysh with Eva Mendes seems stronger than anything so we won't hold our breath.
The CW/Original Films
This couple danced into our hearts after starring in Step Up and stayed there for over a decade. The two met before Tatum was anywhere near the superstar he has become and were clearly each other's rocks as they navigated their come-ups in Hollywood. Plus, can you even think of a better-looking couple?! Didn't think so. Their 2018 split was tragic, but the two handled it like the mature adults they clearly are. Since their breakup, they've been seen out and about together with their child. They were also quick to dispel any rumors about what caused their split — lamenting they'd just grown apart but there was no wrongdoing on either side. At least if we have to endure celebrity breakups like this, we get to see an example of exes who truly stay friends!
Happy Madison Productions/Village Roadshow Pictures
Even more devastating that Jen and Justin or Brad and Angelina was the breakup of Jen and Brad. They were the golden couple of the '90s (literally, with that blonde hair!) when their careers were on fire. He was the biggest movie star, she was the biggest TV star. What could go wrong?! Their split when Brad met Angelina led to "Team Jen" and "Team Angelina" shirts being made, that's how passionate people were about this couple! Though, surprisingly, when they said that they were friends post-split, they weren't kidding. We didn't quite believe it at the time, but there's no more proof needed that Pitt showing up at Aniston's 50th birthday bash in 2019!
Relativity Media/Marvel Studios
This hilarious couple proved over the years that they were the funniest, most down-to-earth couple in Hollywood. The two met at a table read for a film they were doing together and the fireworks were undeniable. They got engaged soon after and ended up getting married on a whim after a friend's wedding! We love a spontaneous couple! Their playful attitude and clear love for each other is what makes this one of the harder celebrity breakups to process. What went wrong between this silly couple? While they may not be together (and Pratt is getting remarried!) it's clear there is no bad blood between the two stars. Faris even volunteered to officiate Pratt's upcoming nuptials!
Revolution Studios/DC Entertainment
Garner and Affleck were the most low-key, go-with-the-flow, normal couple in all of Hollywood. After a high-profile relationship with Jennifer Lopez, Affleck ended up with another Jen that seemed much more his speed. They lived a quiet life together with their kids and didn't buy into the drama of their industry. But, alas, it was not built to last. The two announced their split in 2015 amid Ben's issues with substance abuse and reports that it was taking a toll in their marriage. Here's why we love them despite their breakup, though: Garner has never stopped being there for Affleck. When he had issues with substance abuse again in 2018, she was there to lead the intervention and get him the help he needs. She's all in when it comes to supporting her baby daddy! Celebrity breakups are tough, but these two make it look almost easy.