Mismatched Celebrity Couples That Still Have People Scratching Their Heads

Hollywood relationships may seem like revolving doors, but every so often, a really unlikely pair comes along that leaves us scratching our heads. We’re talking about the stars you’d never put together in a million years! And, yes, while some of these relationships did fizzle out as quickly as they began, others defied all of our expectations.

1. Angelina Jolie and Billy Bob Thornton

Jolie and Thornton’s intense PDA and choice to wear vials of each other's blood around their necks meant that their three-year marriage was like candy to the media. The pair were even set to adopt a child before their relationship ended abruptly in 2003.

2. Pete Davidson and Kate Beckinsale

Fresh off the back of his breakup with pop star Ariana Grande, SNL funnyman Davidson cozied up with the then-45-year-old Beckinsalde in early 2019. The match certainly turned heads — despite lasting four months in total. Even to this day, some fans can’t believe it happened.

3. Hugh Hefner and Crystal Harris

The Playboy Mansion was no stranger to beautiful women roaming its halls. But in 2012, Hef decided to turn his love palace into a love nest when he wed the 23-year-old Harris. The couple remained married until his death in 2017.

4. Mary-Kate Olsen and Olivier Sarkozy

Even with their 17-year age gap, Olsen fell head-over-heels for the French banker way back in 2012. The couple wed in 2015 after a three-year courtship, but they’re now divorced.

5. Michael Jackson and Brooke Shields

Despite the platonic nature of their relationship, Jackson called Shields "one of the loves of [his] life" and even discussed marriage with her. But the pair gradually grew apart and hadn't seen each other in 16 years upon Jackson's death in 2009.

6. Sandra Bullock and Jesse James

What was "America's sweetheart" doing with a motorcycle bad boy? That was everyone's thought when Bullock and James wed in 2005. Unfortunately, a series of infidelities on James' part led to a messy divorce for the couple in 2010.

7. Chelsea Handler and 50 Cent

What started as a bit of harmless flirting on Handler’s talk show became a hot and heavy fling in 2010. Though the host and the rapper split after just a few months, they still remain friendly.

8. Carmen Electra and Dennis Rodman

In 1998 Rodman filed for an annulment from Electra after just nine days of marriage — claiming he was of "unsound mind" at the time. Though the pair eventually reconciled, they wound up divorcing four months later.

9. Katy Perry and Russell Brand

What seemed like a marriage built to last ended after just 14 months, as conflicting schedules and Perry's desire to not rush into having children drove them apart. Brand apparently never spoke to Perry again after texting to say that he was divorcing her.

10. Sacha Baron Cohen and Isla Fisher

A couple since 2002, Baron Cohen and Fisher didn't marry until she converted to Judaism in 2010. The couple has three children together, and Fisher says they sometimes get confused when their dad slips into one of his characters.

11. Kat Dennings and Josh Groban

While you might think it was Groban’s charming sultry vocals that drew her in, Dennings admitted that it was actually his witty tweets that made her fall for him in 2014. They dated for almost two years before mutually parting ways in 2016.

12. Avril Lavigne and Chad Kroeger

When two Canadian music stars get together to collaborate, love is bound to blossom. Lavigne and Kroeger married in 2013 — just a year after the two began writing music together. But in 2015 they announced their split.

13. Pamela Anderson and Kid Rock

After calling off their two-year relationship in 2003, Anderson and Rock reunited in 2006 and were married for just under a year. Many believe Anderson's infamous appearance in Borat was the final blow to their marriage.

14. Cory Booker and Rosario Dawson

Booker’s political campaign wasn’t the only reason he made headlines. When word got around that he was dating Hollywood actress Rosario Dawson, reporters lapped it up. Alas, it wasn't to last. Their split was confirmed in February 2022.

15. Renée Zellweger and Kenny Chesney

Despite all signs pointing to a great marriage, Zellweger filed to have her union with Chesney annulled just four months after their May 2005 wedding. Citing "fraud" as the reason, the couple later clarified that their respective marriage goals hadn't been clear when they wed.

16. Ashton Kutcher and Demi Moore

Even with 16 years separating them, Moore had "never been so happy" when she and Kutcher wed in 2005. But Kutcher's infidelities became too much to overlook, and Moore filed for divorce in 2011.

17. Tom Cruise and Cher

Evidently, Cher did believe in life after love. The iconic singer dated a laundry list of famous men following her split with Sonny Bono — including Cruise, whom she called one of her "best lovers."

18. Sean Penn and Madonna

Penn and Madonna married on her birthday in 1985 and then starred in 1986's Shanghai Surprise together. And the singer's third album, True Blue (1986), was dedicated to Penn. The good feelings wouldn't last, however, and the couple divorced in 1989.

19. Julie Bowen and David Spade

Modern Family’s Bowen and career comedian Spade seemed quite the mismatched pair when they were a couple in 2002. They dated for just a year before deciding to call it quits.

20. Madonna and Michael Jackson

The King of Pop and The Material Girl attended the 1991 Oscars together as a couple. They did kiss that evening, but their fling ended not long after.

21. Christian Bale and Drew Barrymore

We wouldn’t be surprised if you had never heard about this A-list couple. Bale and Barrymore were both teenagers at the time, you see. And it wasn’t like they were in it for the long haul, either. Barrymore chose not to call him back after their first date. Ouch.

22. Will Smith and Tyra Banks

Back in his The Fresh Prince of Bel-Air days, Smith became involved with Banks, who guest-starred on a few episodes of the show.

23. Justin Timberlake and Fergie

As a teen idol and NSYNC star, Timberlake had a casual fling with the then 23-year-old Fergie. But after a bit of fun, the singers decided to say bye bye bye.

24. Matthew McConaughey and Janet Jackson

Sparks flew when these two met at the 2002 Grammys — although McConaughey initially denied it, claiming they were "just friends." But in 2006 Jackson admitted that they were something of an item — albeit very briefly. “I guess we did [date]... It was just for a minute, that's why I'm so hesitant to mention it,” Jackson told Upscale magazine.

25. Madonna and Vanilla Ice

Madge briefly dated rapper Vanilla Ice. They parted ways after eight months, but not before Ice appeared in Madonna's raunchy photo book, Sex. Ice reportedly didn’t realize he’d be featured in the book and, feeling “embarrassed and ashamed,” he ended their relationship. That’s what he told News of the World in 2011, anyway!

26. Rihanna and Shia LeBeouf

We give full credit to both stars for going outside their comfort zones, but this relationship lasted for exactly one date in 2007. “The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends,” LaBeouf told Playboy magazine in 2009.

27. Simon Cowell and Carmen Electra

Cowell has high standards, but apparently, Electra met them — for the time being, anyway! Their short-lived romance ended after Carmen allegedly caught him with another woman. Though she still doesn't say they dated.

28. Keanu Reeves and Diane Keaton

Reeves apparently fell for Keaton during the production of Something's Gotta Give. If there was anything between them, though, it was kept under wraps. Keaton still refuses to acknowledge the rumored romance.

29. Enrique Iglesias and Sofia Vergara

Prior to Modern Family launching her to stardom, Vergara dated the "Bailamos" singer in the late 1990s. Details are few and far between, but it can’t have lasted long as Vergara moved onto Craig David in 2003.

30. Taylor Swift and Taylor Lautner

You can go ahead and add Twilight's Lautner to Swift's list of ex-boyfriends. Apparently, the shared first name wasn't enough of a connection to keep their romance going.

31. Jennifer Aniston and Paul Rudd

Aniston is best known for her relationship with Brad Pitt, but that came after a short romance with Paul Rudd. He later appeared in Friends, but as Phoebe's boyfriend, not Rachel's. Though the pair did team up as a married couple in the 2012 movie Wanderlust.

32. Natalie Portman and Moby

When musician Moby started seeing Portman in the early 2000s, it apparently drew a fair amount of backlash from the nerd community. Moby told Page Six in 2006, “You don't date Luke Skywalker's mom and not have them hate your guts.”

33. Madonna and Tupac

Madonna got cozy with Tupac in the early '90s, telling David Letterman that dating the rapper had her “feeling very gangsta.” Sadly, he dumped her in the form of a handwritten letter. The document later went up for auction.

34. Sandra Bullock and Ryan Gosling

It turns out that Miss Congeniality is just like the rest of us in that she had a soft spot for Ryan Gosling. The pair dated for a year, despite a 16-year age gap.

35.  Lance Armstrong and Ashley Olsen

Reporters spotted these two getting hot and heavy in public, but the cyclist and actress parted ways after that. Armstrong’s handlers were apparently concerned that dating a much-younger woman would damage his image...

36. George Clooney and Lucy Liu

Before his marriage to Amal, Clooney was notorious for his inability to commit. That may be why he and Liu never got serious, despite going out on several dates over the years.

37. Sylvester Stallone and Brigitte Nielsen

Stallone and Nielsen started off as a scandal. She was 17 years younger than him, and Stallone had left his wife Sasha Czack for her. They married in December 1985, having known each other for only a few months. They divorced two years later.

38. Bruce Springsteen and Julianne Phillips

Bruce Springsteen and Julianne Phillips met in 1984 and got hitched only months later. Alas… marry in haste, repent at leisure. Springsteen then had an affair with musician Patti Scialfa, and in 1988 he and Phillips divorced. “I placed [Phillips] in a terribly difficult position for a young girl, and I failed her as a husband and partner,” Springsteen wrote in his 2016 memoir, Born to Run.

39. Kim Basinger and Prince

Apparently, Basinger became so besotted with Prince back in 1989 that she took herself off to his house and stayed there until her worried family brought her back. Prince reportedly kept some evidence of her presence, though. His track “Scandalous Sex Suite” allegedly contains sounds of him and her… well, you can guess.

40. Brooke Shields and Nicolas Cage

In 1987 Shields and Cage were each other’s date to the premiere of the film Moonstruck, in which Cage starred alongside Cher. However, it turned out to be only a short-lived fling. By the next year, it was all over.

41. Geena Davis and Jeff Goldblum

Frequent co-stars Davis and Goldblum were husband and wife for the last part of the 1980s — they wed in Las Vegas in 1987. However, by 1990 it was all over. The couple remain friends, and in 1992 Goldblum told People magazine, “I think we were lucky to get together, and we both had a great time.”

42. Christie Brinkley and Billy Joel

Christie Brinkley was Billy Joel’s original “Uptown Girl.” They married in 1985, on a yacht no less, and quickly became even more world-famous as a couple. Although they broke up in 1994, they remained friends as well as co-parents to their daughter, Alexa.

43. Lea Thompson and Dennis Quaid

Back to the Future actress Lea Thompson met Dennis Quaid on the set of Jaws 3-D, and the pair were very much taken with each other. In 1986, on Valentine’s Day, Quaid asked Thompson to be his wife. However, the marriage never went ahead. The couple split up the following year and went on to marry other people.

44. Helen Mirren and Liam Neeson

Neeson was head over heels for Mirren in 1980, and they made a home for themselves in London. Unfortunately, the relationship only lasted five years. In 1994, Mirren told The New York Times of the breakup, “He handled it with great elegance and grace.”

45. Brad Pitt and Christina Applegate

In 1989 Christina Applegate went out on a date with heartthrob Brad Pitt. Unfortunately, before it ended, she apparently ran off with another man. Sebastian Bach of heavy metal band Skid Row claimed that he was the other party.

46. Tommy Lee and Heather Locklear

Heather Locklear was famous in the 1980s, but Tommy Lee was infamous as the frontman for heavy metal band Mötley Crüe. When they married in 1986, it raised many eyebrows — how could such a sweet actress choose a wild hellraiser for a husband? Yet they did actually last until 1994 in the end, longer than Lee’s first marriage.

47. Cindy Crawford and Richard Gere

The supermodel and the A-list actor made for one of the most attractive power couples ever. They met in a refreshingly normal way — at a BBQ in 1988 — but their relationship was anything but normal. In 1991 they married in Las Vegas, in a rushed last-minute ceremony. Even so, they stayed together for four more years before splitting in 1995.