Selena Gomez and Justin Bieber
Selena Gomez and Canadian pop sensation Justin Bieber dated from 2010 to 2018. Bieber's repeated run-ins with the law, physical altercations, and DUI arrests characterized their relationship. And you may not know this, but Selena herself made numerous, not-so-secret trips to treatment. The two had an intense Instagram feud after Bieber shared pictures of himself kissing a new girlfriend, which boosted attention on the couple.
In the end, everyone moved on when Selena dated German-Russian DJ Zedd in 2015 and Canadian artist The Weeknd in 2017. Gomez is currently engaged to music producer Benny Blanco, while Bieber is now married to Hailey Baldwin.
Miley Cyrus and Liam Hemsworth
In 2009, pop sensation Miley Cyrus began dating Liam Hemsworth, the brother of Australian actor and Thor star Chris Hemsworth. After becoming engaged in 2012 and then married in December 2018, Cyrus threw a wrench in the relationship in August 2019 by declaring their separation. With both sides of the couple having huge celebrity status, the breakup led to inevitable rumors. However, questions were eventually answered.
Citing irreconcilable differences, Hemsworth filed for divorce eleven days later. Fans thought Miley had cheated on Liam after pictures of her kissing Kaitlynn Carter appeared online, despite the initial suspicions that Liam was having an affair.
Yoko Ono and John Lennon
The Beatles were a beloved UK band that originated in Liverpool, so it was a shock when John Lennon entered a relationship with aristocratic Japanese artist Yoko Ono, who was thrice married and had previously been admitted to a psychiatric hospital. After divorcing their partners and falling in love, John and Yoko were married in 1969. Even with this, the story of their breakup is not what you might expect.
The largest band in the world broke up as a result of their relationship, which was particularly poisonous. According to legend, George Harrison's discovery of Yoko consuming one of his Digestive biscuits led to the Beatles' split.
Angelina Jolie and Billy Bob Thornton
Angelina Jolie, the daughter of Jon Voight and an aspiring actress, dated actor Billy Bob Thornton in the 1990s. Before the relationship even started, fans were confused by the relationship as Thornton was 20 years older than her. Although they frequently showed their love for one another in public after being married in 2000, their relationship was strange. Curious about this so-called ‘strangeness’?
The pair exchanged underwear, had matching tattoos of their brands, and wore vials of each other's blood around their necks! Three years later, they broke up. Billy Bob has had six marriages and four children from three different women.
Gavin Rossdale and Gwen Stefani
Gwen Stefani, the lead singer of No Doubt, married Gavin Rossdale, the lead singer and guitarist of Bush, in 2002 after they first met in 1995. Sounds like the perfect marriage, right? Before she filed for divorce in August 2015, the couple had three sons together and had been married for two happy decades. But if they were so happy, where did everything go wrong? Gavin Rossdale had been having an affair with their nanny, it turns out.
Despite being devastated by Gavin's adultery, poor Gwen bounced back quickly and, three months later, began dating country music sensation Blake Shelton!
Scott Disick and Kourtney Kardashian
At a gathering in 2006, Kourtney Kardashian met Scott Disick. Although their romance became a staple of Keeping Up With the Kardashians, it was quickly ruined by his use of substances, parties, and alcohol. After Disick was pictured with Los Angeles stylist Chloe Bartoli in 2015, the couple called it quits. They reunited in 2016 after Scott mellowed and said goodbye to his partying ways.
However, within a year, Disick was caught kissing two models in Miami. Kourtney is currently married to Travis Barker, the drummer for Blink-182, and the two have a son together.
Dean McDermott and Tori Spelling
While filming Lifetime's Mind Over Murder in 2005, Tori Spelling got to know actor Dean McDermott, who was married at the time. McDermott's infidelity with Spelling was revealed by Us Weekly in 2013. After McDermott’s divorce, he and Tori eloped in Fiji and welcomed five children together. On their reality TV show, True Tori, the attention-seeking pair discussed their financial struggles.
This was because Tori received only $800,000 from her late father's $500 million fortune. In a 2023 Instagram post, McDermott revealed their separation after 18 years of being together.
Jesse James and Sandra Bullock
Sandra Bullock had already dated Ryan Gosling and Matthew McConaughey (lucky girl!), but she was in for a wild ride when she married actor Jesse James in 2005. Sure, this might sound like a dream, but after 5 years into the relationship, a number of ladies came forward and said that they had affairs with Jesse. As you might expect, Sandra Bullock was devastated by this discovery, so the relationship did not last much longer.
He apologized in public, saying, "The vast majority of the allegations reported are untrue and unfounded." Bullock filed for divorce, and James went to treatment to keep the union intact. Sandra fell in love once more with photojournalist Bryan Randall, who tragically died in 2023.
Elizabeth Taylor and Richard Burton
Richard Burton, a Welsh thespian with a gravelly voice, met beautiful English-American actress Elizabeth Taylor when she played the Egyptian queen in Cleopatra (1963), and he played Mark Anthony. Their relationship was even more turbulent, extravagant, and jet-setting than the pyramids. Can you believe it? However, in a sad turn of events, alcohol turned out to be the only thing they both loved more than one another.
Despite their repeated divorces in 1974, 1975, and 1976, they remained in love to the end. Liz was distraught when Burton died in 1984, saying, "Maybe we loved each other too much."
Jessica Simpson and John Mayer
In 2006, following her divorce from Nick Lachey, Jessica Simpson began dating musician John Mayer. However, a couple of years into the coupling, Jessica Simpson discussed how Mayer made her feel uneasy and undeserving of his affection in her autobiography, Open Book. In 2010, Jessica broke up with Mayer after he made disparaging remarks about her in a Playboy interview. John has since apologized for his mistreatment of her.
In more recent times, Jessica married former NFL star Eric Johnson and had 3 children with him. Sadly, they announced their separation in January after 10 years of marriage. Want a fun fact? Mayer also dated Jennifer Aniston, Katy Perry, and Taylor Swift.
Lindsay Lohan and Samantha Ronson
In 2008, British DJ Samantha Ronson and wild child Lindsay Lohan dated. Although Lohan used to remark, "She's a wonderful person, and I love her very much," the relationship ended after just a year because it was "too toxic to survive." Due to their aggressive partying and public yelling battles, the couple's actions garnered some not-so-great media attention. But their story does not end here.
When things got out of hand, Samantha threw Lindsay out, changed the locks on her house, and forbade her from going to her sister Charlotte Ronson's design show. The reason surrounding this odd behavior is somewhat unknown.
Sienna Miller and Jude Law
On the set of Alfie in 2003, Jude Law, a handsome English actor, met Sienna Miller, a stunning English actress, and they had a connection. The following year, the attractive pair became engaged after falling in love. However, in 2005, it was discovered Jude had had an affair with his children’s nanny. After Jude Law’s adored performance in the ‘Sherlock Holmes’ franchise, this was a huge shock. Sienna stayed for a while before ending the relationship when he publicly apologized.
Jude has since been linked to 3 different women and has seven children: 3 with his first wife before Sienna, Sadie Frost, 1 with Samantha Burke, 1 with Catherine Harding, and 2 with his current wife, Phillippa Coan. Sienna has two daughters: one with actor Oli Green and another with actor Tom Sturridge.
Christine McVie and Lindsey Buckingham
One of the most toxic bands ever is Fleetwood Mac! Guitarist Lindsey Buckingham spent ten years with vocalist Stevie Nicks, and singer Christine McVie was married to bassist John McVie. However, Stevie left the ship and began dating Mick Fleetwood, the drummer. After that, Christine and Lindsey started dating, but their relationship was unstable and full of infighting because of substances and the bandmates' infidelity.
In 1980, Stevie and Christine even got into a brawl on stage! So, as you have probably already guessed, their relationship did not last long, but it had a huge impact on the band’s dynamic.
Britney Spears and Kevin Federline
The marriage between Britney Spears and Kevin Federline is undoubtedly the most "toxic" relationship in pop music. The singer wed her "talentless" backup dancer in 2004; some people even called him a golddigger. Britney filed for divorce despite the fact that they had two sons together. The general belief is that Britney lost her mind after making an appearance on their own reality TV show, Britney and Kevin: Chaotic.
She famously shaved her head and drove while holding her son on her lap (not a great look!). As you could’ve guessed, K-Fed was granted custody of the kids following a protracted and contentious legal struggle.
Frida Kahlo and Diego Rivera
You need a couple of fiery Latino artists if you want a truly passionate, toxic marriage that is full of happiness, sadness, art, and hurling china at walls! Similar to how MC Skat Kat and Paula Abdul performed "Opposites Attract," and how Frida Kahlo, a 22-year-old Mexican woman with a monobrow, married Diego Rivera, who was overweight and had been married twice already, in 1929.
One of Diego's numerous extramarital romances was with Kahlo's sister. After an ugly breakup in 1939, the couple remarried in 1940. In 1954, Kahlo died with Diego by her side. It's unknown why the couple remained together after such a controversial marriage.
Megan Fox and Machine Gun Kelly
Megan Fox, the stunning Transformers actress, said in 2022 that she was seeing Machine Gun Kelly, a popular musician. Their strange connection revolved around cosplay costumes, vampirish blood makeup, and entrapment. MGK had an unhealthy fascination with Megan, which was evidenced when he proposed with a thorned engagement ring in 2022. How odd! "It was getting toxic between them, and they were fighting a lot," acknowledged a close insider.
Fox finally had enough and announced the engagement was canceled in March 2024. They, however, seem to be back together, as they announced Megan had given birth to a baby girl in March 2025.
Angelina Jolie and Brad Pitt
When Angelina Jolie and Brad Pitt met while filming Mr. and Mrs. Smith in 2005, she ended Brad's marriage to Jennifer Aniston. Their couple name was "Brangelina," a portmanteau, and they were married in France in 2014. They had three biological children and three adopted children. Angelina alleged that Brad verbally and physically assaulted her and their kids on a flight despite their idyllic-looking marriage.
In September 2016, she filed for divorce, and it was finalized in 2019. It has not been confirmed, but sources say that Angelina Jolie was able to keep custody of their 6 kids and now lives a happy, quiet life.
Kim Kardashian and Kanye West
Kim Kardashian, a reality TV personality, socialite, and heiress, married rapper Kanye West in 2014. Initially, everything appeared to be in good health. Together, they have four children: Psalm, Chicago, Saint, and North. However, Kanye appeared to lose the plot and began to believe his own messiah complex and the marriage was shattered by suspicions of infidelity. Since their divorce, Kanye has been showing more odd behavior, which has only increased the level of publicity surrounding the relationship.
When Kim and Kanye got divorced in 2022, she allegedly received the largest divorce payment ever - a whopping $2.7 billion! But you have to consider whether the money is really worth the controversy Kim Kardashian has to face every day.
Marilyn Monroe and Arthur Miller
Marilyn Monroe and Arthur Miller were married in 1956. She was the most attractive movie star in the world. He was bespectacled and a nerdy playwright. Quite an odd mix for a couple, right? Especially when you consider how desirable Marilyn Monroe was in her prime. When Marilyn Monroe saw Arthur Miller's writings about their "disappointing" marriage, he broke her heart. Marilyn's only desire was to have a child, but Miller didn't help her after she miscarried twice.
Monroe struggled with drugs and had an affair with actor Yves Montand in an attempt to get revenge. Miller, however, didn't care. In 1961, they got divorced, and Miller didn't even go to Marilyn's funeral when she died in 1962.
Pamela Anderson and Tommy Lee
The bad boy drummer for Mötley Crüe married Baywatch star Pamela Anderson in 1995 after just four days of dating. That has got to be a world record! They had one of the most toxic marriages, with accusations of things getting physical, public yelling battles, and heavy usage. A contractor, after not being paid for work done, notoriously released an erotic film, Tommy and Pammy, after breaking into their safe.
When Lee kicked Pamela in 1998 while she was holding their baby Dylan, he was imprisoned for six months. Pamela filed for divorce the same year. Lesson learned: do not get married after 4 days of knowing someone.
Denise Richards and Charlie Sheen
Hollywood bad boy Charlie Sheen married Denise Richards, a stunning actress and one of the ‘Bond Girl’ actors, in 2002. After she accused her husband of threatening her life and having an excessive love for adult beverages, their relationship ended despite the fact that they had two daughters. Denise stated the reasons for their 2006 divorce as "marital turmoil, sobriety issues, and criminal problems."
Charlie was prohibited from approaching her and their daughters within 300 feet after she obtained a restraining order against him. Approximately half a million dollars in child support is allegedly still owed by Sheen to Richards.
Sharon and Ozzy Osbourne
Every great man has a terrific woman behind him, and this relationship was the definition. Although Ozzy has long been a washed-up singer, the Prince of Darkness was the driving force behind Black Sabbath, a heavy metal band, from the 1960s to the 1980s. Over the years, Sharon has served as his rock, manager, wife, and caregiver, so their breakup was a huge surprise to the Osbourne fans. For forty years, Sharon tolerated Ozzy's drinking and substance use while raising his kids.
Along with becoming a judge on America's Got Talent and X-Factor, she also rose to fame on the reality TV series The Osbournes. However, their breakup didn’t last long, and they’re still married today!
Madonna and Sean Penn
On the set of her "Material Girl" music video, Madonna met actor Sean Penn, whom she married on her 27th birthday in 1985. Their relationship was ruined due to claims of violence and infidelity, even though it should have been a romantic fairy tale. The irascible Penn even ended up in jail for assaulting a stalking photographer. So, with this news, it's not hard to believe that Sean Penn was the problem.
Penn was a pampered brat, according to her Majesty's entourage, who detested her husband. In 1989, Madonna finally got a divorce from Sean. Now, it's only Madonna’s name that remains in the headlines.
Katy Perry and Russell Brand
Russell Brand and Katy Perry met while filming Get Him to the Greek. In 2010, they were wed in a Hindu ceremony in India. However, 14 months later, the "controlling" English comedian texted her to dissolve the marriage because he was envious of her popularity. The kicker? He sent the text just before Katy's scheduled New Year's Eve performance. Russell Brand was accused of severe emotional and physical abuse by four women in 2023.
After being called a predator, Brand's career came to an end in shame. Since then, only Katy Perry remains loved by her fans, and it's easy to see why.
Ava Gardner and Frank Sinatra
Nancy Barbato and Frank Sinatra were married and had three kids together. However, a legendary rollercoaster relationship began in 1948 between him and the beautiful actress Ava Gardner. Following a DUI joyride that resulted in a "shootout" that broke storefront windows, they were both taken into custody. After forcing Nancy to get a fast divorce, Frank and Ava got married in 1951.
The marriage between Ole Blue Eyes and Ava was tense and full of jealousy, and they had multiple affairs. Their divorce was formalized in 1957 after their relationship terminated in 1953.
Khloe Kardashian and Lamar Odom
After barely one month of dating, Khloé Kardashian wed NBA player Lamar Odom in September 2009. Lamar quickly left the show when their wedding was broadcast on Keeping Up With the Kardashians. As you might already know, he struggled with alcohol and substances. In 2013, he was arrested for DUI and had affairs with other women. With this information, it's no surprise their relationship did not last very long.
After he was discovered comatose in Las Vegas in 2015, the couple got a divorce. He suffered 12 strokes, heart attacks, and kidney failure as a result of his drinking. A lesson for the youngsters: just say no!
Mel Gibson and Oksana Grigorieva
Mel Gibson, a Hollywood star, was arrested in 2006 for DUI and for using racist epithets on the arresting officer. He met Oksana Grigorieva, a Russian pianist and vocalist, in 2007, and their daughter was born in 2009. When she published startling, foul-mouthed recordings of an inebriated Gibson hurling his rage at her, their relationship came to an end. With the end of the relationship being so aggressive, the breakup gained a lot of publicity.
Then, after accusing Mel of assaulting her, Oksana obtained a restraining order against him. Seldom has a well-liked public person fallen from grace so quickly, but Mel Gibson is solely responsible for his own demise.
Elin Nordegren and Tiger Woods
Tiger Woods possessed everything. He earned millions of dollars, was the world's best golfer, and was married to the beautiful Swedish au pair Elin Nordegren. However, the National Enquirer reported in 2009 that Tiger had been having an affair with a nightclub manager in New York City. After that, Tiger's life fell apart as scores of other women came forward to say they had affairs with him.
According to rumors, Nordegren would get back together with Tiger for $350 million, but she ended their marriage and took $100 million in the divorce settlement!
Kim Basinger and Alec Baldwin
In 1993, Alec Baldwin married Kim Basinger, and two years later, the glitzy Hollywood couple welcomed a daughter, Ireland. However, the true pyrotechnics began when Kim and Alec broke up in 2000. Baldwin spent a million dollars during the years-long dispute between the ex-couple over custody of Ireland. However, some shocking news came out that meant that Baldwin had no chance of winning the legal battle.
Baldwin swore in a voicemail he left for his daughter, age 11, in 2007, calling her a "rude, thoughtless little pig." Doing what they do best, TMZ posted the voicemail online. With the public being able to see it, Kim Basinger won custody.
Amber Heard and Johnny Depp
After Johnny Depp married actress Amber Heard in 2015, she accused him of mistreating her and filed for divorce and a restraining order against him a year later. On a monthly basis, Amber asked for $50,000 to "support her lifestyle." Heard promised to give the $7 million that Depp paid as a divorce settlement to a charity, but she pocketed it instead. You’re likely to have already heard about this case, as it was followed by thousands online.
The 2022 Depp v. Heard defamation case had the entire globe on edge. The world witnessed Amber's true nature, and Depp was virtually exonerated of any wrongdoing.
Courtney Love and Kurt Cobain
Frontman Kurt Cobain began dating Hole singer and Sid and Nancy actress Courtney Love after "Smells Like Teen Spirit" made Nirvana the largest band in the world in 1991. The next February, on Waikiki Beach in Hawaii, they were married and had a daughter named Frances Bean. But their relationship was stormy, tumultuous, and destructive - the absolute definition of ‘toxic’.
Kurt tragically committed suicide on April 4, 1994, due to substance abuse and health issues. Although Courtney and Kurt Cobain were awful influences on one another, many conspiracy theories blame Courtney for Cobain's death.
Heidi Fleiss and Tom Sizemore
In 2001, Tom Sizemore began dating Heidi Fleiss. Chernobyl was not as toxic as the romance between the heavyweight actor and the notorious Hollywood madam. Tom's long-term substance problems caused him to become violent, and in 2003, Fleiss accused Sizemore of assaulting her, burning her, and dragging her across a room. Does not sound like a great dynamic for a relationship, does it?
Sizemore was imprisoned for 90 days for DV. He was then checked into treatment by Robert De Niro. Tom was accused of beating his new girlfriend in 2017. In 2023, he passed away.