Those celebrities do the nuttiest things. Like heroin. Prostitutes. Heroin-addicted prostitutes, and appearances in Adam Sandler movies. But the famous tend to reserve their most puzzling moves for the bedroom, when they inexplicably hook up with other celebrities that are either from a very different social circle, or seemingly from a very different planet.
Here now is a list of lovestruck celebrities and their biggest romantic blunders. And, by the way, if some of these couplings come as a shock to you, it’s for good reason. Whether it’s a stag film from forty years ago or an ill-considered tryst with a meth-addled starlet, most famous folks are quite skilled at burying embarrassing secrets from their past.
10. Jim Brown and Gloria Steinem
Even if you’re no football fan, and thus unfamiliar with Jim Brown’s claim to NFL greatness, a quick glance at his resume tells you everything you need to know about why this man shouldn’t have ever dated ’60s and ’70s feminist icon Gloria Steinem. He was a famously manly star of a brutally violent game. After retiring from the NFL he pursued a career as a actor, appearing in classic works of cinematic art like Slaughter’s Big Ripoff. His personal life has been riddled by numerous accusations of violence against women — with one case resulting in Brown’s blaming his actions on his wife’s menstrual cycle. In other words, he spent much of his adult life making feminism necessary.
But according to Brown’s autobiography, the two somehow became a couple shortly after Steinem interviewed the former NFL star for a magazine in 1968. Even stranger is the post script: Brown’s fling with Steinem stirred up jealousy with his then-girlfriend Eva Marie Bohn-Chin, kick-starting an argument that resulted in Brown being accused of tossing Bohn Chin down a balcony. Must have been that time of the month.
9. Julia Roberts and Lyle Lovett
In the early ’90s, Julia Roberts had reached the height of her Tinseltown powers. She was young, beautiful and as famous as any woman on the planet. So naturally she did what most glamorous starlets would do: She decided to date and briefly marry the strangest looking human ever.
The unlikely couple met on the set of The Player in 1992 and stumbled into elopement a mere three weeks later. By March of 1995, sanity had been sufficiently restored, Julia remembered that she was stupidly gorgeous and sleeping with a guy with the worst melted face since the Nazi who dared open the Ark Of The Covenant, and the couple divorced.
8. Flava Flav and Brigitte Nielsen
It’s hard to imagine ’80s hip-hop icon/all-purpose oddball Flava Flav finding any love interest that couldn’t be described as “mismatched.” But Flav’s connections with the 6’2″ Danish born, four-time divorcee is trippy stuff, even by reality TV standards.
With little in common except for their strangely public battles with substance abuse, the couple split up in short order, sparing Flav the honor of becoming husband number five for Nielsen.
7. Bette Midler and Geraldo Rivera
You’d think an assignation between a young Geraldo Rivera and a vibrant Bette Midler would be fodder for romance novelists everywhere. Well actually, you wouldn’t think that, we hope. But you’d think such an encounter would at least have been memorable. Gay community mascot Bette Midler disagrees though, claiming the experience was “nothing to write home about.” Adding that the seduction was made possible by “poppers” (ask your parents,) Middler claims to have been drugged up and groped by the man she lovingly described as a “slimeball.”
The Fox News personality was kinder in his retelling of the event in his 1992 autobiography Exposing Myself. He praised Midler for her voluptuous figure and sexual appetite. But in the same book, he claims to have bedded over 1000 women. To date, the couple has announced no plans to rekindle their relationship.
6. Liz Taylor and Larry Fortensky
If you’re thinking to yourself that this pair doesn’t strictly qualify as a “celebrity couple,” because the groom, construction worker Fortensky, hardly qualifies as a celebrity, well, that’s kind of the point. Taylor may have married with alarming frequency, but tying the knot with a nobody just wasn’t her style. Husband number one, for example was young hotel heir Conrad “Nicky” Hilton (yes, Paris’s uncle.) From there she went on to esteemed British actor Michael Wilding, then Oscar-winning producer Mike Todd, then… okay, there are too many to list here, but if you’ve got a free weekend, check out Liz’s complete matrimonial history.
How a high school dropout and career construction worker found his way into such company is unclear. But the place of their fateful meeting may provide a clue: the couple first locked eyes during a stay at the Betty Ford Clinic. They married three years later at Michael Jackson’s famed Neverland ranch and divorced in 1996. The reason for their parting? Fortensky no longer wanted to be known as “Mr. Elizabeth Taylor,” apparently preferring to make a name for himself in the glamorous world of construction work. To date, post-marriage fame has eluded him.
5. Gene Simmons and Diana Ross
Simmons took time away from his ongoing relationship with the available female population of the Western hemisphere to devote his attentions to refined diva Diana Ross. Miss Ross’s notoriously ravenous need for singular attention would have made her an unlikely candidate for being with a man not especially familiar with monogamy. And, to no one’s great surprise, the couple split up before Simmons could be frightened into his cave by the sound of wedding bells.
4. Michael Jackson and Lisa Marie Presley
Lisa Marie Presley spent her childhood being doted on by her legendarily rich, eccentric pop star father. With that in mind it kind of makes sense that she’d later fall in love with a legendarily rich, eccentric pop star. Except for the part about that pop star being Michael Jackson.
This odd couple first met in 1975 when the seven-year-old Presley saw the seventeen-year-old Jackson (already an international star) perform in Las Vegas. Decades later, they married and divorced soon after. They had no kids but the proud couple gave birth to a number of pricelessly awkward public moments.
3. Marilyn Manson and Evan Rachel Wood
When this sweet-faced ingenue found herself in the company of demonic rocker Marilyn Manson, their pairing seemed more like the result of a hostage situation than a loving tryst. After a few years of a public ups and downs, it appears that Wood has escaped with no visible damage.
On her relationship with Manson, she claims the eyeliner-clad singer-songwriter “gave me what I felt I’d missed out on, where you get to experiment and cut loose and change and grow. I lived 50 lifetimes in those four years.” But let’s face it, that’s probably code for, “he tried to drink my blood.”
2. Sammy Davis Jr. and Linda Lovelace
Chances are, you’ve never thought you’d see the names Sammy Davis Jr. and Linda Lovelace in the same sentence. Well, just try to imagine the icons themselves sharing a heated embrace (sorry for the image). If the rumor mill is to be believed, the pioneering porn star found herself in the Candy Man’s arms on at least one occasion. Decades later, the rumor mill is still cranking out bizarre speculations about the lives of both participants — bestiality, bisexuality, satanism, orgies — as if the very fact that these two highly different people wound up naked in the same bed isn’t weird enough.
1. Cher and Anybody
With the recent cancellation of her plans to wed a much younger Hell’s Angel, Cher seems to be on something of a hiatus. But all it takes to remind us of what a dizzying ride her dating life has been is a (partial) roll call:
Tom Cruise (16 years younger), Val Kilmer (13 years younger and insane), Richie Sambora (much younger and a musician), Sonny Bono (musician and egotist) Gene Simmons (blood-spurting musician and egotist) Rob Camilletti (bagel maker), Tim Medvetz (biker), Warren Beatty (Hollywood himbo), etc.
Summing everything up, Cher says, “A girl can wait for the right man to come along but in the meantime that doesn’t mean she can’t have a wonderful time with all the wrong ones.” Well said. But still … seriously, why Sonny?