25 WTF Hollywood Couples


Hollywood is a weird place, full of weird things, and weird people; so it shouldn’t be much of a surprise when some of these weirdos pair off with each other.

Here are 25 of the oddest and most random couples in Hollywood:


Pete Doherty and Kate Moss


The first couple on the list is one that was most famous for being such a friggin’ disaster. English singer and perennial bad boy Pete Doherty and Kate Moss were in the British tabloids for years for being a) an unlikely pair and b) trashbags.  

These two dated on and off for a few years before finally breaking up in 2007, mercifully not bringing any children into the world.


Britney Spears and Kevin Federline

Jason Merritt/FilmMagic

You’ll no doubt remember this couple for their Golden Globe winning reality show: Britney & Kevin: Chaotic (ed. Note: THIS SHOW WAS NOT NOMINATED FOR ANYTHING EVER, NO WAY). Britney Spears, pop sensation and proud supporter of rage-based haircuts, married former dancer and professional wrestler (I SWEAR TO RIC FLAIR) Kevin Federline and had what no one called a whirlwind romance for the ages.

The couple split but at least they got two pretty cute sons out of the whole deal.


Russell Simmons and Hana Nitsche


Russell Simmons dated German supermodel Hana Nitsche in ‘12, but the couple broke up less than a year later in ‘13. Most people probably best remember Simmons for his 11 year marriage to Kimora Lee and wearing a fitted Yankees cap with everything because, trademark look.

While Simmons was dating Nitsche in 2012, Lee would often vacation with them because going on vacation with your ex is totally normal and of course won’t place any strain on your relationship at all at all.


Simon Cowell and Carmen Electra


American Idol judge and British-Alan-Thicke-covered-in-sunburnt-calluses, Simon Cowell dated 90s bombshell Carmen Electra when the two met on Britain’s Got Talent.

Their relationship lasted two months and ended when Electra caught Cowell with Lauren Silverman, another woman with bad taste in bed. Silverman would later carry Cowell’s seed and bear for him a son.


Jessica Alba and Cash Warren


When Jessica Alba married some dumbhead named Cash in 2008, folks around the globe were a bit puzzled. No one really knew who Cash Warren was, no one knew why anyone would name their child Cash, and no one knew why a grown man, with autonomy and freedom of choice, would still opt to present himself to the world as “Cash”.

Regardless, they dated, got married, have two daughters named Sixpence and Nickels, and a newborn son.


Michael Jackson and Lisa Marie Presley


Michael Jackson met Lisa Marie Presley (best thing to come out of Elvis in ’68) in 1975 but the two didn’t start “dating” until the early 90s. They married in 1994 but divorced only two years later, probably, well, because, you know. I mean come on, Michael Jackson.


Dennis Rodman and Madonna


Dennis Rodman and Madonna were really hot and heavy for an action-packed two months in 1994 before calling it quits. Rodman, in his autobiography, and clearly without any pretension or ego, stated that “Madonna wanted to have my babies” but left out the part where she dumped him upon realizing he was not, as she once believed, Wesley Snipes in Demolition Man.


Katy Perry and Russell Brand


Katy Perry and Russell Brand married in 2010. They had a traditional Hindu ceremony in Rajasthan, (OF COURSE THEY WOULD – INSERT GROANS AND EYE ROLL, PLEASE) but divorced in 2012. Perry claims that Brand had told her he was filing for divorce via text message, and then straight up ghosted her. This is totally not fitting some of Brand’s views on religion.


Courtney Love and Edward Norton


Courtney Love and Edward Norton met on the set of 1996’s The People vs. Larry Flynt (WOODY HARRELSON, I GOT YOU, BABY!!!!) and began dating shortly thereafter. The couple remained together until 1999 when they broke up because Love decided to leave him for some jabrone who ended up stealing all her money. Edwards is said to have consoled himself by preparing for the new millennium WILLENNIUM, blasting the now-classic Will Smith jams, Wild Wild West and Will 2K.


Colin Farrell and Elizabeth Taylor

The Independent

Colin Farrell, man who inexplicably continues to wear two earrings and a goatee, told Ellen Degeneres (and about a million folks watching at home) that he had a brief affair with Elizabeth Taylor before she passed away, although he admitted it was never consummated.  

If that counts as a relationship, then from 1992-2012 Cindy Crawford and I were married.