We are taking a cheeky in-depth look back at some of the bizarre, unlikely and outrageous celebrity couples that you may have forgotten once graced the covers of your favorite celeb gossip magazines.
Madonna and Tupac
In 2015, Madonna shocked the world when she admitted to having had a secret relationship with the late, great rapper Tupac Shakur. In a letter penned by the rap legend from his jail cell in 1995, he explored the difficulty of their inter-racial pairing, apologizing to the Material Girl for the dissolution of the relationship. The letter would later be put up for auction with a starting bid of $100 000.
Michael Jackson and Madonna
This was a match made in pop star heaven; the king and queen of pop dated briefly in the nineties. Madonna revealed that she made the first move courting MJ, saying that he was ‘a little shy.’ The superstar pair first made headlines when they showed up together at the Oscars in 1991. The fling was short lived but will forever live on in the hearts of MJ and Madge fans everywhere.
Zoe Saldana and Marco Perego
The “Guardians of the Galaxy” star welcomed her third child recently — a little boy named Zen, with her actor and artist husband Marco. “Marco and I are elated to share the news of the birth of our son Zen. We couldn’t feel more blessed with the new addition to our family. #threeboys… oh boy!” she wrote.
Robert De Niro and Grace Hightower
De Niro and his wife, split up, only to renew their vows in 2004. She is an actress and singer, and has two children with the famous actor.
Nicole Kidman and Lenny Kravitz
She’s the porcelain-skinned Australian beauty, he’s the wild rock musician with a nipple ring – not exactly what you would call a compatible pair. Despite the oddness of their partnership, Nicole Kidman and Lenny Kravitz reportedly had a private and intense relationship from 2002 to 2003. Kidman even confirmed that the pair were engaged before the relationship unraveled. The stars have remained close friends.
Evan Rachel Wood and Marilyn Manson
This might have been a proven case of ‘opposites attract.’ From 2007 to 2010, Evan Rachel Wood and Marilyn Manson would have a romantic relationship. The rocker met the blue-eyed actress when she was 18 at a Hollywood party, and undeterred by their 18 year age gap, the two became involved. The relationship was controversial which seemed to be exactly what Wood intended. She was quoted saying, “I met somebody that promised freedom and expression and no judgments… I was craving danger and excitement.”
Bradley Cooper and Renee Zellweger
Yes, that’s right. The hangover hottie and Bridget Jones dated for two whole years before parting ways. The couple was reportedly madly in love before the surprise split. Tabloid speculation claimed that there was another woman involved but it was Bradley’s ambition that caused the two to drift apart. Renee’s career has since nosedived while Cooper is now one of Hollywood’s most sought-after actors.
Kim Kardashian and Nick Cannon
Before she hooked up with Rap royalty, Kanye West, Miss K found herself on the arm of Nick Cannon. Kim was best known as Paris Hilton’s stylist and sidekick, while Cannon was an ex-Nickelodeon star with a budding movie career. Oh, how times have changed. Cannon went on to marry (and divorce) Mariah Carey and Kim skyrocketed to superstar status with a sex tape, one divorce, another marriage, a couple of kids and a media empire that keeps on growing.
Sarah Jessica Parker and Robert Downey Jr
These two were the picture of young love in the nineties. Before she was Carrie Bradshaw and he was a Marvel superhero, the two were a cute, gawky couple navigating their early careers together. The pair were together for seven long years before Downey’s personal struggles with drugs and alcohol addiction became a dealbreaker for fresh-faced Sarah. Downey has said, “I liked to drink, and I had a drug problem, and that didn’t jibe with Sarah Jessica because it is the furthest thing from what she is.”
Richard Gere and Cindy Crawford
Cindy Crawford and Richard Gere were once A-list royalty but their high-profile relationship has since been forgotten. The supermodel was only 26 when she tied the knot with the then 42-year-old Gere in 1991. The couple officially divorced four years later, in 1995. When asked in a recent interview if the two were still friendly, Crawford’s response was surprisingly cold; “…He’s gone back to being, like, ‘Richard Gere’ again, like a stranger.”
Kate Hudson and Owen Wilson
The gorgeous Kate Hudson and everyone’s favorite funnyman Owen Wilson have a tumultuous history. Few fans might remember but the pair dated on and off between the years 2006 and 2008. After their initial split, Wilson had some very public personal issues, the star reportedly attempted suicide over the particularly nasty break up. The pair would rekindle their romance a few months later but the reconciliation was fleeting and the pair permanently parted ways in ’08.
Brad Pitt and Christina Applegate
Back in 1989 when Brad Pitt was a relatively unknown newcomer and platinum-haired Christina Applegate was Hollywood teen royalty, the surprising pair hooked up very briefly. Applegate showed up with Brad as her date to that year’s MTV Movie Awards but reportedly fled mid-date and left with another A-list hunk. To this day, the actress won’t confirm who the mystery Casanova was.
Kiera Knightley and Jamie Dornan
It’s hard to believe that the skinny guy in those horrendously baggy jeans would go on to become the sex symbol behind Christian Grey. Jamie Dornan and Kiera Knightley hooked up in the early noughties and dated for a little over two years. Thankfully, the actors are now happily married to other people and have considerably better fashion sense.
Cher and Tom Cruise
In a recent television interview, 67-year-old Cher proclaimed that a young Tom Cruise was ‘in her Top 5’ list of former lovers. The odd pair supposedly had a heated fling in the late eighties before Cruise hit the big time and became a couch-jumping, Scientology-loving action star.
Mila Kunis and Macaulay Culkin
In one of Hollywood’s more bizarre romantic match-ups, Mila Kunis and Macaulay Culkin had an intensely private and serious relationship for eight years. The starlet and previous child star would split up in 2011. Since his days as a child superstar, Culkin has faced some personal battles with drugs and alcohol addiction but he’s recently reemerged looking much healthier. Kunis would go on to marry Ashton Kutcher.
Ryan Reynolds and Alanis Morisette
The nineties gave us a few odd couplings, one of which being Ryan Reynolds and angsty singer Alanis Morisette. The loved-up pair walked many a red carpet together looking particularly smitten. They were engaged in 2004, but the two would never make it down the aisle. They split in 2008 and Morisette penned her subsequent album as an ode to their heartbreaking break-up.
Jennifer Aniston and John Mayer
America’s beloved girl-next-door had a well-publicized fling with the singer, songwriter and serial womanizer John Mayer. The pair split in 2009 amidst rumors of Mayer’s infidelity. Despite his bad boy reputation, Mayer has the highest regard for his former flame, saying “That woman was the most communicative, sweetest, kindest person.”
Leonardo DiCaprio and Naomi Campbell
It’s been well-documented that Leonardo DiCaprio has a special love for leggy supermodels, what few people might not know, that one of his first high-profile romances with a model was with none other than Naomi Campbell. The two reportedly dated in 1994, before the actor made it big with his late nineties roles in Romeo + Juliet and Titanic. The pair, who are both known to enjoy a champagne-fueled yacht party, are still good friends.
Heath Ledger and Heather Graham
Heath and Heather met in Prague while both filming movies in 2000. Bonding over mutual interests and a shared sense of humor, the couple would date for a year before splitting. Ledger would meet his future love, Michelle Williams, on the set of his iconic movie Brokeback Mountain. The actor would meet a shocking and untimely end in 2008 when he was found unresponsive in Manhattan apartment. The coroner’s report classified the star’s tragic death as the result of an accidental overdose.
Ashton Kutcher and Brittany Murphy
Pint-sized Brittany Murphy and the lanky hunk Ashton Kutcher would fall madly in love on the set of their movie Just Married. The heated romance lasted a couple of months, with the two young stars calling it quits in 2002. Kutcher would go on to marry Demi Moore while Murphy’s days would end in unforeseen tragedy. Murphy would die of cardiac arrest at the age of 32. The official report claimed she had died of pneumonia despite strangely elevated levels of numerous legal drugs detected in the actress’s system. Her husband at the time, screenwriter, Simon Monjack, would die five months later with similar symptoms. Both deaths remain mysterious.
Carmen Electra and Dennis Rodman
In 1998, the Baywatch bombshell and the basketball bad boy headed to Vegas for an impromptu wedding. Carmen Electra and Dennis Rodman’s marriage would last less than a year. In a recent interview with Oprah Winfrey, Electra reflected on the short-lived romance, “Our relationship was very passionate. When it was good, it was amazing,” she said. “And when it was bad, it was the worst.”
Jack Nicholson and Lara Flynn Boyle
Jack Nicholson is known as a notorious ladies’ man. The Hollywood legend and Lara Flynn Boyle started dating after Nicholson asked the brunette out while her then-boyfriend, actor Dave Spade, was standing right beside her. Lo and behold, the celebrity pair was a couple mere months later. Spade confirmed the story, saying “Nicholson asked Lara Flynn Boyle out in front of me…” Despite the outrageous 33 year age gap, the pair would date for a year.
Rhys Ifans and Sienna Miller
You will most probably recognize actor Rhys Ifans from his role as Hugh Grant’s grubby roommate Spike in the 1999 film Notting Hill. In a strange stroke of fate, the actor landed himself a date with British beauty Sienna Miller. The odd coupling would stay together for a year before a messy break-up in 2008. Ifans was a self-confessed drug abuser who did not take the split well. He claimed to have ‘learned his lesson’ after parting with Miller, proclaiming he was done with famous girlfriends.
Ashley Olsen and Lance Armstrong
In 2007, former child actress Ashley Olsen and cyclist Lance Armstrong were spotted getting cozy in a New York restaurant. Fearing that the relationship would mar his public image, Lance’s publicist urged him to break off the fling, given that Olsen was 15 years his junior. Sadly, there were bigger mishaps that would destroy the cyclist’s once-thriving career. In 2012, Armstrong was banned from competitive cycling and stripped of his many titles over his admitted use of performance-enhancing drugs.
Scarlett Johansson and Ryan Reynolds
Strangely, this celebrity pairing seems to have been completely forgotten. Scarlett Johansson and Ryan Reynolds were briefly married from 2008 to 2011. Reynolds is now besotted with his second wife, actress Blake Lively. In a 2016 interview, Johansson insinuated that ‘competition’ between the two actors was the reason behind the failed marriage.
Katy Perry and Russel Brand
Singer Katy Perry and bad boy social activist Russel Brand was the couple that nobody saw coming. She was a kitsch pop princess and he was a foul-mouthed Brit with a high IQ and a drug problem. In spite of their blaring incompatibility, the two would wed in 2010 after only having dated for a year. With Katy heading off on her world tour, leaving her new husband back in the UK, the doomed duo eventually divorced in 2011.
Matthew McConaughey and Janet Jackson
Matthew McConaughey and Janet Jackson met backstage at the 2002 Grammy Awards. This was way back when, before Matthew was an Oscar winner and Jackson was still super famous (sorry, Miss Jackson). The pair supposedly instantly hit it off. The brief fling was never confirmed but a source reportedly spotted the barefoot actor leaving the home of the pop star the following morning after the award show.
Julia Roberts and Lyle Lovett
Julia Roberts is widely regarded as one of the world’s most beautiful women. In 1993, after a three-week whirlwind romance, the gorgeous actress eloped and married the funny-looking country crooner Lyle Lovett. Let’s just say, that Lovett has yet to make it on to People Magazine’s ‘Most Beautiful’ list. The bizarre pairing would remain married for two years before Julia’s demanding career became between them.
Britney Spears and Colin Farrell
Back in 2003, Colin Farrel was the up-and-coming, potty-mouthed, cigarette-smoking Irishman that the press simply loved to provoke. To the shock and delight of fans and members of the paparazzi, Farrel showed up to the premiere of his film, The Recruit, with Britney Spears on his arm. For a hot minute, the unlikely pair made worldwide headlines. Unsurprisingly, the fling was brief. The Princess of Pop later said in a magazine interview, “He’s the cutest, hottest thing in the world! …But it was nothing serious.”
Sandra Bulock and Ryan Gosling
Long before Ryan Gosling solidified himself as a leading man, the young star dated everyone’s favorite all-American actress, Sandra Bullock. The pair met on the set of the movie Murder by Numbers and dated for a year before calling it quits in 2002. The unlikely pairing raised a few eyebrows – Sandra was 16 years older than Ryan at the time. Gosling would go on to marry the gorgeous Eva Mendes.
Erik Asla Tyra Banks
In 2013, Tyra Banks started dating Norwegian photographer Erik Asla. Tyra gave birth to a son via surrogacy on January 27, 2016.
Angelina Jolie and Billy Bob Thornton
Angelina Jolie is known today as a passionate philanthropist, committed mother of six and demure United Nations ambassador. Back in 2000, the actress was an unpredictable wild child with a peculiar taste for danger. She married fellow actor Billy Bob Thornton after meeting him on the set of their 1999 film Pushing Tin. The weird couple was seemingly besotted with one another, getting inked with tattoos of each other’s names while Angelina even wore a vial of Thornton’s blood around her neck. The intense relationship would disintegrate and end in divorce in 2003.