Never Forget These Celebrity Trainwreck Relationships From the ‘90s and ’00s

There’s no denying that Pamela Anderson and Tommy Lee were the ultimate rock n’ roll couple in the late ‘90s, but between sex tape scandals and Lee’s arrest for spousal abuse, the couple decided to call it quits around 1998. Despite being divorced, Lee and Anderson continued to see each other on and off, and made public declarations for their love in 1999 and again in 2008. But with a toxic history of bad headlines, the public stopped taking them seriously. Anderson went on to marry three more times, but is currently divorced from former husband Jon Peter. Lee was engaged a few times after Anderon and is currently married to social media celebrity Brittany Furlan. Let's be honest, she's iconic.

Reeling from her divorce from Nick Lachey, Simpson began dating Mayer on and off for a year starting in 2006 (although Mayer claims the couple frequently slept together after the breakup). She opened up about just how awful he was in her memoir Open Book. In it, Simpson describes Mayer as that guy, one who would make her feel insecure on all accounts — and not worthy of his love and attention. And while you may choose to take that with a grain of salt, Mayer’s infamous 2001 Playboy interview proves he views her as ‘sexual napalm’ versus a real human being. Mayer has since apologized for his treatment of Simpson, but it’s too little too late.

RELATED: The most famous celebrity couples from 1979 to 2020.

Ted Danson met Whoopi Goldberg when he appeared as a guest on The Arsenio Hall Show in 1998. They became fast friends but it wasn’t until they appeared in Made in America together that the two celebs began an affair. Once the media got wind of their secret relationship, the couple was making headlines on every tabloid across every grocery store line in the world. The scandal led to the end of Danson’s 16-year marriage to second wife, Cassandra Coates. The divorce cost him a cool $30 million, and like most celebrity love stories, the relationship between Goldberg and Danson ended soon after.

Drew Barrymore met Tom Green on the set of Charlie’s Angels in 2000 and became engaged that same year before marrying in 2001. They divorced nine months later and haven’t spoken since, and maybe that’s because they should never have been together in the first place. This relationship wasn’t really a trainwreck, but it was an odd pairing that the public had a difficult time buying into, especially as Barrymore and Green toyed with the media by teasing their nuptials across late-night television shows like SNL and The Tonight Show with Jay Leno. The odd pairing, though short-lived, was memorable, to say the least.

YOU MAY ALSO LIKE: Celebrities you didn't know were best friends.

Jude Law and Sienna Miller fall victim to the classic Hollywood tale of man meets woman, man asks the woman to marry him and then sleeps with the nanny. At least, that’s how it went down after Miller and Law met on the set of Alfie in 2003 and fell deeply in love. They were engaged by 2004, and in 2005, the nanny of Law’s children went public with a paid story that she had been sleeping with him. Law issued a public apology, and Miller stuck around until the following year when she finally broke things off. She now claims that dating Law was a direct result of her failing acting career.

The world was thrilled when Sandra Bullock married motorcycle man Jesse James in 2005, and not because James was a prize — we just wanted to see Sandy happy. But that happiness came to a grinding halt in 2010 when several women came forward with claims that James had been engaged in multiple affairs throughout their marriage. He issued a public apology, but Bullock went ahead with a divorce that was finalized just over eight months after the affairs went public. Bullock went on to thrive in both her personal and professional life, while James remained the same trash he always was.

Back when MTV was the most popular music and entertainment station, Carson Daly was at the top of his game as the broadcasting channels adored VJ. While hosting a spring break series, Daly met Reid, and the two fell for each other hard. They were engaged within nine months of dating but never made it down the aisle. It wasn’t that their relationship was a particularly bad one. Still, the rush of fame and love went to both of their heads and inevitably, stories of infidelity began swirling around their impending nuptials. In the end, they just couldn’t make it work. It happens.

Who could forget Bennifer? It’s all we could talk about in 2002 after Jennifer Lopez and Ben Affleck became engaged. The two celebs met while filming the box office bomb Gigli and began a highly-publicized romance that overshadowed the film's release and prompted JLo to divorce her second husband and former backup dancer, Cris Judd. This relationship doesn’t have a particularly messy story, but the weight of the media attention it gained placed the couple under such a vivid microscope that it began to feel like we were all marrying JLo. Sadly, the couple never made it down the aisle.

If there is anyone to blame for the fall of Britney Spears, it’s that idiot Kevin Federline. This unlikely duo met in 2004 and married each other three months later. The relationship gained wide media attention, especially because Federline had recently broken up with actress Shar Jackson, who was still pregnant with their second child at the time. Then came the reality show Britney & Kevin: Chaotic, and honestly, the rest is pretty much a mismatch of scenarios that repeatedly painted Spears in a bad light. By 2006 the couple divorced, just eight weeks after her second son was born and right before the world witnessed Spears infamous breakdown.

SEE ALSO: 37 celebrities you never knew dated.

Tori Spelling and Dean McDermott met in 2005 while filming Lifetime’s Mind Over Murder. As the story goes, the couple fell madly in love, and both decided it was a swell idea to cheat on their partners with whom they were married. Less than a year later, they eloped in Fiji and started a family, a book, and a reality show. This couple relished in the media attention they were given and continued to document their lives, including health scares, financial issues, and all of McDermott’s infidelities. But, this couple has embraced all of their baggage and continues to support their mess 14 years later.

SEE ALSO: 21 celebrities who married their mistresses.

Jersey Shore aired at the end of 2009, and it was here that Sammi “Sweetheart” Giancola and Ronnie Ortiz-Magro met and fell for each other. But the relationship was anything but sweet. This couple was toxic from the very beginning as they allowed jealousy, drunken fits, rumours and emotional abuse to cloud their relationship constantly. Of course, both individuals were accused of cheating and blatant flirting, and you can probably count on one hand how many times they were actually kind to each other both on and off screen. Despite that, the couple stayed intact for the duration of the show's original run, but couldn't make it to the reunion portion of the series.

Tiger Woods was first known as the world's greatest golf player but became more famous for the very public breakdown of his marriage to Elin Nordegren. In 2009, Nordegren discovered that Woods had been cheating on her with Rachel Uchitel. After confronting him about it, stories emerged that Nordegren charged after Woods with a gold cub, causing him to flee to his car for safety. But woods was on sleeping pills at the time and ended up crashing his car. Woods reportedly paid Uchitel to stay silent, but more than ten other women came forward with stories of infidelity, which drove Woods and Nordegren to a very public and very pricy divorce.

RELATED: Celebrities with the weirdest, wildest prenups.

Real Housewife Denise Richards and Charlie Sheen’s relationship began in 2000, but not much of it has been positive. In 2005, while pregnant with their second child, the couple released a statement that they would be separating. They tried to reconcile on more than one occasion, but Ricards accused Charlie of prescription medication abuse, violent mood swings, compulsive gambling, and use of pornography before leaving him again (and again). In 2012, Sheen entered a very awkward and embarrassing public rage war that saw him flinging insult after brutal insult at Richard's way over Twitter and multiple interviews. By 2020, the couple seemed to be laying nice again.

Amy Winehouse and Blake Fielder-Civil began their very unhealthy relationship in 2007. Both individuals were addicted to drugs and alcohol and would often emerge in public bloody and bruised due to drunken fits that got them there. Fielder-Civil openly admitted to the British media that he introduced Winehouse to crack cocaine and heroin. The destructive relationship continued to make headlines until they divorced in 2009, but Winehouse’s addiction to drugs and alcohol continued, and ultimately took her life in 2011 when she died from alcohol poisoning.

During the height of her fame, Lindsay Lohan began publicly dating celebrity DJ Samantha Ronson. It was around this time that Lohan became more known for her constant partying and A-list pals than her work in film. It wasn’t that Lohan and Ronson were awful to one another, but it was clear from the get-go that they were not meant to be. Lohan faced public scrutiny for her casual approach to the same-sex relationship, and the couple were snapped, looking like a drunken mess for the majority of their courtship. Lohan would later describe the relationship as “toxic,” but also admitted they were able to become friends afterwards.

RELATED: No gal pals here: 10 lady loving celebrity couples.

Sophia Bush and Chad Michael Murray met on the set of One Tree Hill in 2004, fell in love, and got married and divorced five months later. Bush first attempted to have the marriage annulled, citing fraud, but the claim was denied, and the divorce made final. Of course, rumours of infidelity came to light, but years later, Bush has admitted that it was merely a poor judgement call and that neither party should have been married in the first place. While the couple still had to work together on the series for years, Bush states that the producers exploited their relationship and divorce, making the divide even worse.

In 2004, Nick Carter famously began dating Paris Hilton, a union that lasted only seven months. However, within those seven months, the couple made headlines for their hardcore partying and eventually for Carter’s alleged abuse towards Hilton. The abuse allegations were never substantiated, but when Aaron Carter entered a very public fight with his brother in 2019, he brought the topic up again, claiming the abuse was real and called on Hilton to back up the story and finally call Nick out. Hilton remained silent on the subject, and the story eventually died down once again.

Before Angelina Jolie married Brad Pitt and adopted 100 babies, she was best known for her strange relationship with Billy Bob Thornton. The former couple met in 1999 while filming Pushing Tin. It was bad enough that Thornton snuck out of his relationship with Laura Dern to low key marry Jolie, but that’s not the worst part. What followed was a series of bizarre events like the vials of each other's blood they wore around their necks, matching branded tattoos, underwear swapping and very over the top PDA on red carpets. The couple divorced after two years over compliments of conflicting lifestyles. Huh?

Although this couple is happily married with a child right now, the beginning of their relationship was the stuff of reality show blunder. They met in 2007 while Montag was filming The Hills, and began a relationship that caused a permanent rift between Montag’s close friendship with the series front-runner, Lauren Conrad. Montag and Spencer’s relationship became very popular, and the couple took advantage of their fame in a series of icky publicity stunts that the crowd eventually grew tired of. There was fighting, separations, claims their entire relationship and marriage was fake, etc. But in the end, they somehow found a way to make it work.

They may have only dated for a minute, but for us, it felt like the longest minute known to man. In the year 2000, when Hilary Duff and Aaron Carter were only 13 years old, they began dating on and off until 2003. Carter was accused of also dating Lindsay Lohan, and thus, the relationship between him and Duff fizzled. But that’s not the dramatic part. Over the years, Carter would continue to mention Duff in interviews, claiming she was “the love of his life” and that he regrets how he treated her. In 2014, Duff finally addressed Carter’s comments over the years and basically told a reporter that the relationship was so long ago that she almost forgot it existed at all. Ouch!

YOU MAY ALSO LIKE: The worst celebrity couples in pop culture history.