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Oddest Celebrity Couples in History

Updated on February 12, 2018
Jaynie2000 profile image

With an eye on fashion, art, music and movies, Jaynie keeps her finger on the pulse of pop culture. Why? Because it's fun.

Celebrities are just like anyone else. They eat, sleep, work, laugh, cry and fall in love. The difference is that their relationships are much more high profile than those of the average person, so when they pair up with what may appear on the surface to be an odd choice, the tabloids go crazy. It seems that no one can get enough celebrity gossip. To feed the need for hot Hollywood gossip, this hub is dedicated to the some of the strangest couples in recent memory.

Liza Minnelli and David Gest

When Liza Minnellli married David Guest it left most people scratching their heads. On one hand it seemed only fitting that the stage legend and performer most beloved by legions of gay fans married someone that was widely rumored to be a homosexual. ON the other hand, David’s odd, plastic-like appearance made everyone including plastic queen Joan Rivers wonder what Liza could have been thinking. They married in March of 2002, separated in July of 2003 and finally divorced amidst rumors of spousal abuse from both camps, in April 2007.

Michael Jackson and Lisa Marie Presley

Their union made great fodder for the tabloid press. When they married in 1994, few people actually believed they were in love, but through it all, MJ and Lisa Marie continued to profess their love and insist that they were physically intimate, a mental image no one wanted rattling around their consciousness. Whether they succumbed to the pressures of stardom and public disbelief or the rumors of a loveless marriage were actually true, the couple divorced two years after they wed.

Brigitte Nielsen and Flavor Flav

Brigitte Nielsen was once a statuesque beauty that was romantically involved with such man’s men as Arnold Schwartzenegger, Sylvester Stallone and Mark Gastineau, so when she hooked up on the set of reality-TV show, The Surreal Life, with the show’s star and Public Enemy frontman, Flavor Flav, it seemed, well, strange to say the least. The two were such a curiosity, that VH1 gave them their own show, aptly called, Strange Love. Ultimately the two parted ways but not before becoming a pop culture phenomenon.

Angelina Jolie and Billy Bob Thornton

This couple was nothing if not passionate. Their on-screen canoodling and declarations of love and where they fuc*%& left the general public feeling uneasy yet unable to turn away. They further piqued the public interest by wearing vials of each other’s blood around their necks, and almost no one who knew of them could figure out how such an incredible beauty could find herself in love with a haggard, older man that looked as if he were drunk half the time. Angelina began to mature and shortly after their second wedding anniversary she filed for divorce, clearing the way for her to adopt her son Maddox as a single parent.

Julia Roberts and Lyle Lovett

When the gorgeous, girl-next-door movie star with the oversized grin and infectious laughter married the quirky, country crooner, jaws dropped. Few if any knew they had been dating. Lovett’s curly pompadour, ragged features and crooked grin were in stark contrast to Robert’s flowing red locks, and perfect, toothy smile. The couple were notoriously separated for most of their union because of his tour schedule and her film career and ultimately, the oddest looking couple for whom we all were rooting, divorced.

Anna Nicole Smith and J. Howard Marshall

Anna Nicole Smith had 500 million reasons to love her husband, oil tycoon, J. Howard Marshall, and each one of those reasons had a dollar sign in front of it. She was only 26 years old when she married the 89 year old Marshall. Despite having made a name for herself as a Guess jeans model and Playboy centerfold, Marshall’s bankroll was apparently too good to pass up. The honeymoon didn’t last long, as Anna Nicole left her reception to jet off to Greece alone. The two were married for 14 months, until Marshall’s death in 1995, after which Anna Nicole became embroiled in a protracted legal battle with E. Pearce Marshall, J. Howard’s son, over her husband’s millions. Anna Nicole succumbed to an accidental overdose of prescription medications on February 8, 2007.


Marilyn Manson and Evan Rachel Wood

She was a 19 year old movie star with classic good looks that harkened back to old Hollywood and he was a goth, shock-rocker who wore more make-up than Estee Lauder when the unlikely pair met in 2007. They had an on-again, off-again relationship, including an engagement until they split for good in 2010. Most people might have assumed that the rocker was too dangerous and unattractive for the talented young actress, but in 2011, Wood gave the world another potential reason for the split. She is a bisexual. Perhaps that’s what attracted her to the androgynous performer in the first place.

Woody Allen and Soon-Yi Previn

Of all the unusual celebrity couples out there, no one elicits more “ewws,” than that of Soon Yi Previn and Woody Allen. Soon Yi was adopted by Allen’s long time partner, Mia Farrow and her former husband, Andre Previn and says that she never considered Allen to be any sort of father figure. The union permanently damaged his reputation in Hollywood, where relationship scandals are commonplace, but incest is always frowned upon, though technically, because Allen never adopted her nor married her mother, the relationship was not incestuous. Despite their 35 year age difference and worldwide scrutiny over how they became acquainted, Allen and Previn remained together, married and have two adopted children of their own.

50 Cent and Chelsea Handler

Really? 50 Cent and Chelsea Handler? Is it possible that the snarky blond with the acerbic wit and the hard core rapper that survived so many bullet wounds he was more like a wedge of swiss cheese than an actual person were really an item? Both denied that there were dating, but as celebrities tend to do, they took full advantage of the publicity that their rumored affair garnered. They have been photographed together at several dinner “dates” and other events, including one photo of the two in bed together about which Handler famously and comically tweeted, “I don’t know why anyone would ever think I’d date a rapper!” So, were they are weren’t they? Perhaps no one but the two will ever know, but if the rumors were true, they may have been one of the most unusual couples of 2010.

Katy Perry and Russell Brand

Whether attending music award shows or working on movie sets together, the pair enjoyed a high-profile, whirlwind courtship that culminated with a romantic, extragavant and traditional Hindi wedding celebration. While Perry oozes with charm and popstar appeal and is worshipped by tweens the world over, Brand is an offbeat, gawky looking British comedian that looks more like he’s living with a perpetual hangover and is in desperate need of a shave and a haircut. Oh well, they say that love is blind and if that is true, it might explain how the perky brunette found love with odd-looking Brand.

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5 out of 5 stars from 1 rating of Oddest Celebrity Couples

© 2011 Jaynie2000


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    • Jaynie2000 profile imageAUTHOR


      9 years ago

      Thanks! I had fun writing it. It's amazing how apparent opposites attract, isn't it?

    • cwarden profile image


      9 years ago from USA

      Great hub! These are some very unusual matchings for sure! I don't watch much TV anymore so I wasn't aware of the 50 Cent and Chelsea Handler rumor - crazy! I'm going to go dig up the dirt on that one now - Thanks!

    • Jaynie2000 profile imageAUTHOR


      9 years ago

      The VERY least! Those two were ridiculous, but I have to admit that I had a morbid fascination with them. They were sooo weird I felt compelled to watch!

    • Fossillady profile image


      9 years ago from Saugatuck Michigan

      You really nailed it. I think flavor flave and Bridgette take the cake! To each his own I suppose! Hollywood is interesting to say the least!

    • Jaynie2000 profile imageAUTHOR


      9 years ago

      Thanks so much. I have to admit, for all the intellectual stuff I do all day, my weekend guilty pleasure usually involves an hour or two of alone time with People magazine.

    • dearabbysmom profile image


      9 years ago from Indiana

      Very entertaining! This is just what I needed on a Friday when I'm not really wanting to work :) Up and funny


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