7 of the Strangest Hollywood Couples of All Time
We have something to admit: Hollywood couples are kind of “our thing.” There’s just nothing more fascinating than watching two famous folks get together! Obviously, the messy breakups are usually just as interesting as the couples themselves, but that’s a different story…
Now, what we love most about Hollywood hookups is the fact that so many of them seem to come out of nowhere. So often we find ourselves thumbing through the gossip rags, saying: How in the heck did these two even meet? Wait, he’s HOW much older than her? Didn’t she just get divorced?? Hey, a hobby’s a hobby, right?
Recently, we decided to take a virtual walk down memory lane to revisit some of the strangest celeb pairings we’ve ever encountered– and boy are they weird. Here 7 examples of famous odd couples that still make us scratch our heads!
Cher and Tom Cruise
We’re not kidding here, folks— once upon a time, Tom Cruise and Cher were actually a couple. In a 2013 interview with Andy Cohen, Cher revealed that she and the heartthrob had a brief fling in the mid-80s.
When asked how the Mission Impossible star was as a lover, she replied that he was “in the Top 5.” Hey— you can’t accuse us of not starting this list off strong!
Natalie Portman and Moby
In 2001, this rising Hollywood starlet briefly dated DJ and musician Moby. They may have looked like an odd pairing, but they had some things in common, namely veganism and their various creative endeavors!
Years after their split, Moby told Spin that his romance with the high-profile actress was doomed from the start— but for quite the unexpected reason. “[Dating Portman] made me the target of a lot of nerd wrath,” Moby explained. “You can’t date Luke Skywalker’s mom and not have [nerds] hate your guts.” Talk about a strange reason to end a relationship!
Sarah Paulson and Holland Taylor
One of the more surprising Hollywood couples of all time surfaced when American Horror Story actress Sarah Paulson went public with Two and a Half Men star Holland Taylor.
In an interview with People, Taylor – who is a whopping 32 years older than Paulson – revealed that she and her partner had been friendly for about 10 years before finally moving their relationship to the next level 2 years ago. These days, the two frequently step out on red carpets together and seem to be going strong. You go, ladies!
Madonna and Tupac Shakur
In 2015, Madonna let quite the secret slip to the world— she and late rapper Tupac Shakur had carried out a secret love affair before his untimely death. It was a revelation that seemed to come out of nowhere, especially since Madonna isn’t usually shy about flaunting her lovers in front of the media.
That said, a prison letter written by the rapper himself and published by TMZ just this past year confirms that the two had quite the deep relationship. In the letter, Shakur writes that he felt that he had no choice but to break up with the pop star because of how their interracial relationship might be perceived in their communities. He punctuated the note by saying “I never meant to hurt you.” Sad stuff.
Mila Kunis and Macaulay Culkin
When it comes to random celebrity couples, it doesn’t get much odder than Mila Kunis and Macaulay Culkin. Long before she married her co-star Ashton Kutcher, the That 70s Show actress dated the former child star Macaulay Culkin but managed to keep the relationship relatively quiet.
Believe it or not, the two stayed strong for a long eight years before calling it quits, and though the duo definitely made for quite the cute couple, Kunis told Howard Stern in 2015 that she never had the urge to tie the knot with him.
Barbra Streisand and Andre Agassi
If you haven’t already figured it out yet, the 90s, in particular, made for some of the strangest celebrity couplings of all time. Case in point: Barabra Streisand and Andre Agassi. The singing legend and tennis champion were together for a short time, but they, unlike some secretive celebs, went public with the relationship, with Streisand even cheering Agassi on from the crowd during his 1993 Wimbledon Match.
Of course, they broke up years ago and went on to marry other people, but that hasn’t stopped the tennis star from speaking out about that time. In his memoir, Agassi says this about his ex-lover: “dating Barbara Streisand is like wearing Hot Lava.”
Whatever that means…
Emmy Rossum and Adam Duritz
Back in 2009, rising star Emmy Rossum shocked Hollywood by going public with Counting Crows singer Adam Duritz, despite there being a big age gap – 22 years for these two! – and plenty of well-known baggage from previous relationships.
When the couple hooked up, Emmy was still recovering from a divorce and Duritz’ name was still attached to a couple of other Hollywood starlets including real-life friends, Courtney Cox and Jennifer Aniston. As it turns out, they did manage to weather the storm for a little over a year, before breaking up in the fall of 2010. Another one bites the dust…
Talk about strange pairs, huh? Which couple is most surprising to you? Do you know of one that you would like to add to the list? Are you part of an odd couple?