Unlikely Valentine: Hollywood's most bizarre celebrity couples

By Adam White

Singer Britney Spears and actor Colin Farrell in 2003. Photo / Getty
Singer Britney Spears and actor Colin Farrell in 2003. Photo / Getty

There's such a rapid turnover of celebrity gossip in modern tabloid media that sometimes A-list couples can slip between the cracks.

But without unearthing the chequered romantic histories of Hollywood's finest every once in a while, you'll never hear the hilarious stories of Colin Farrell mailing Britney Spears offensive T-shirts, or the time Charlie Sheen allegedly shot Kelly Preston.

So spend this Valentine's Day taking a trip down memory lane, one filled with a few likeable if unexpected entanglements, along with those that prove Cupid sometimes just doesn't know what the hell he's thinking.

Victoria Beckham and Corey Haim

Arguably one of the oddest celebrity couples in celebrity coupledom, Victoria Beckham, pop icon turned fashion powerhouse, was once so in love with Corey Haim that she invited him round to meet her parents.

An Eighties teen icon, star of films like The Lost Boys and Licence to Drive, and frequent on-screen partner of Corey Feldman, whose early death signalled yet another forgotten child star meeting a tragic end, Haim spoke about his relationship with the artist formerly known as Posh Spice in 2008.

Actor Corey Haim, 1988. Photo / Getty
Actor Corey Haim, 1988. Photo / Getty

"A car pulls up, this tiny little car, and five girls in these crazy outfits pile out of a car and are like these punk rock chicks, Sid Vicious chicks," he told Access Hollywood. "[They] walk into the studio and me and Vic lock on. Sniper eyes. So I had to hang out with her. It's my obligation as a man to do that."

Beckham revealed, also in 2008, that the pair never consummated their relationship.
"The most we did was kiss," she said. "Looking back, it's hard to work out whether I really fancied him or if I was just a bit of a sad fan."

And just to make this fan-fiction-esque story even weirder, Beckham wrote in her 2001 autobiography Learning to Fly that she was forced to dump Haim after he became jealous of her adoration for Take That. The Nineties, everyone.

Britney Spears and Colin Farrell

No one knows exactly how these two hooked up, Farrell then the newly-minted, drunken bad boy of Hollywood, and Spears in her wild, post-Timberlake, pre-'this is actually really sad' days.

But when they showed up on each other's arms at the premiere of Farrell's action thriller The Recruit, they knew it would create maximum tabloid attention. On the red carpet, Farrell insisted they were "just mates", but were later spotted partying together at the fancy Chateau Marmont.

Singer Britney Spears and actor Colin Farrell in 2003. Photo / Getty
Singer Britney Spears and actor Colin Farrell in 2003. Photo / Getty

Later that same year, tabloids reported that the pair fell out when Farrell mailed Spears a T-shirt saying: "I slept with Colin Farrell and all I got was this lousy T-shirt", and a bumper sticker that read: "Honk if you've slept with Colin Farrell."

It might not be true, but is so oddly specific that you can't help but believe it.

Liam Neeson and Janice Dickinson

Liam Neeson has dated an incredibly versatile array of famous women including Helen Mirren, Julia Roberts, Barbra Streisand and his late wife Natasha Richardson.

But it was his fling with former supermodel and professional reality TV eccentric Janice Dickinson that remains his oddest encounter. While Neeson has never commented on their relationship, Dickinson has been vocal, particularly about one of Neeson's significant attributes. Prepare yourself, readers.

"It was like an Evian bottle fell out of his pants," she told Star Magazine (via Digital Spy) in 2011. "The earth shook. OMG, you don't understand - I swallowed my tongue I was so shocked. This was way before he was famous, too."

Madonna and Vanilla Ice

Madonna has never been shy when it comes to unusual love interests. Or ones that are, in hindsight, incredibly embarrassing. Like the short-lived fling she had with hip hop punchline Vanilla Ice. She even convinced him to pose alongside her in her infamous photo book, Sex. But the book proved to be the couple's undoing.

"I was hurt to be an unwitting part of this slutty package," Ice told the News of the World (via NY Daily News). "We were in a relationship, yet it looked like she was screwing all these other people.

"I thought she was taking pictures and running round naked because she was like that. Then when the book came out I was so embarrassed and ashamed. It was a porno."


Madonna has been less dismissive of their fling, but did reveal in 2015 that she'd rather be stuck on a desert island with her cross-dressing ex Dennis Rodman than Ice.

"He could always wear my clothes," she joked.

Madonna and Tupac Shakur

A less embarrassing past fling for the queen of pop came in the form of iconic rapper Tupac Shakur. Introduced by actress Rosie Perez at the 1993 Soul Train Awards, the pair had a brief relationship, Madonna revealing that the late rapper got her "riled up about life in general."

Shakur's brother Mopreme has also confirmed the relationship. He told Vlad TV (via Vibe): "I don't think it was super serious, gonna get married or some s---. You know how those entertainment relationships go.

"But they both respected each other, so it ended cool. He never talked s--- about her, not to me. And she never talked s--- about him."

Jessica Alba and 50 Cent

This was a strange one, as it's never been explicitly confirmed. But shortly before her engagement to current husband Cash Warren, the actress-turned-entrepreneur Jessica Alba was rumoured to have been in a relationship with famous-rapper-turned-famously-bankrupt 50 Cent.

Jessica Alba and 50 Cent. Photo / Getty
Jessica Alba and 50 Cent. Photo / Getty

Alba was reported to have joined the Get Rich or Die Tryin' star throughout his European tour in 2007, 50 at one point inviting her out on stage during a gig in Amsterdam, where he introduced her as "the most beautiful woman in the world".


Ryan Reynolds and Alanis Morissette

Little symbolises the rapid turnaround of modern celebrity gossip more than the way it's been so easy to forget that Ryan Reynolds wasn't just briefly married to Scarlett Johansson, but was also engaged to Alanis Morissette.

Alanis Morissette and Ryan Reynolds in 2003. Photo / Getty
Alanis Morissette and Ryan Reynolds in 2003. Photo / Getty

The mutual Canadians were a couple for five years as Reynolds began his career ascendance, before they announced their split in 2007.

It is believed Morisette's 2008 track Torch was written about the actor: "I miss your smell and your style and your pure abiding way / Miss your approach to life and your body in my bed" she sings.

Sandra Bullock and Ryan Gosling

After meeting on the set of the psychological thriller Murder by Numbers, Bullock and Gosling started dating, raising eyebrows due to the 16-year age gap between them.

Unusually for both parties (who have largely had incredibly private relationships subsequently), the couple were photographed often: at premieres, events and parties. But they eventually split in 2002.

Sandra Bullock & Ryan Gosling. Photo / Getty
Sandra Bullock & Ryan Gosling. Photo / Getty

Speaking in 2011, Gosling was complimentary to both Bullock and his ex Rachel McAdams: "I had two of the greatest girlfriend of all time. I haven't met anybody who could top them." He would meet wife Eva Mendes that same year, and have two children with her.

Matthew McConaughey and Janet Jackson

Matthew McConaughey has been linked with a litany of major names, including Sandra Bullock, Ashley Judd and Penelope Cruz, but one of his most under-the-radar flings was with pop superstar Janet Jackson.

Janet Jackson and Matthew McConaughey. Photo / Getty
Janet Jackson and Matthew McConaughey. Photo / Getty

After being photographed at the 2002 Grammys, McConaughey denied they were an item ("We swapped some good music and she's a dear lady. She's a sweetheart but we're not dating, we're just friends"), but Jackson later revealed to Upscale Magazine that they were indeed a short-lived couple.

"I guess we did [date]," she said in 2006. "He is a great guy and such a sweetheart. It was just for a minute, that's why I am so hesitant to mention it."

Rosario Dawson and Danny Boyle

While it might seem, on the surface, an unlikely pairing, actress Rosario Dawson and director Danny Boyle were together for a year in the run-up and shoot for the James McAvoy hypnotism thriller Trance.

Rosario Dawson and Danny Boyle. Photo / Getty
Rosario Dawson and Danny Boyle. Photo / Getty

Despite rumours that the two ended up despising each other so much that they refused to interact while promoting the film, Dawson was complimentary of him in a 2013 interview conducted after their breakup.

"I love Danny. He's wonderful and we dated longer than people think we did," she told Net-a-Porter (via Daily Mail). "I respect Danny's privacy, so it's not something we really talk about."

Robert Downey Jr. and Sarah Jessica Parker

Both Robert Downey Jr. and Sarah Jessica Parker broke out in Eighties teen movies, and quickly fell for one another in real life. But, as anyone aware of Downey Jr.'s somewhat volatile history could tell you, their seven-year relationship became messy.

Actress Sarah Jessica Parker and actor Robert Downey, Jr. in 1988. Photo / Getty
Actress Sarah Jessica Parker and actor Robert Downey, Jr. in 1988. Photo / Getty

"[Sarah and I] actually had a very conservative relationship," Downey Jr. told Howard Stern (via Vanity Fair) in 2016. "Considering the fact that she was normal, and I was out of my mind. I did the best I could."

As much as she tried to keep their relationship intact, Parker has revealed in recent years that Downey Jr.'s well-documented addiction to alcohol and drugs pushed her away.

"It felt like I had entered an alternate universe of really scary associations and a habit that had become genuinely scary," she recalled on Marc Maron's WTF Podcast in 2016.
"I'm thrilled for his health and well-being now," she added.

Carey Mulligan and Shia LaBeouf

After meeting on the set of Wall Street: Money Never Sleeps, Shia LaBeouf and Carey Mulligan started dating. But as Mulligan sought marriage and children (she went on to marry Mumford & Sons frontman Marcus Mumford) and LaBeouf seemingly lost his mind for a brief period, they were forced to go their separate ways.

"Carey is not just an actress, she is a great human being, a sweet girl and super intelligent. Our thing came down to not having compatible work/lifestyles," he told the Sunday Times (via Daily Mail)

"We were always travelling, and had sensibility differences that weren't conducive to living with one another. I'm harder on myself and my surroundings than she is, and we had a culture shock in terms of meeting her parents and vice versa.

"She's happy as hell right now, and we wouldn't have been able to make it like that. She was chasing marriage, family, kids more than I was."

Nicole Kidman and Q-Tip

Following her divorce from Tom Cruise, Nicole Kidmanseemed to set her sights on musicians: along with a brief fling with Lenny Kravitz and marriage to country star Keith Urban, she also briefly dated the legendary hip hop artist and A Tribe Called Quest bandmember Q-Tip.

"He's very a talented musician, isn't he?" Kidman was quoted by Fox News in 2003. "But I don't know much about that whole world."

Tip dated Kidman throughout the awards season for The Hours, accompanying her to events and to Oscar parties, before they parted ways.

Charlie Sheen and Kelly Preston

Actor Charlie Sheen and actress Kelly Preston in 1989. Photo / Getty
Actor Charlie Sheen and actress Kelly Preston in 1989. Photo / Getty

Charlie Sheen and Kelly Preston were an item for three years at the tail end of the Eighties. Sheen has also spent many of the succeeding years denying that he once shot her.

In an infamous tabloid tale that wasn't properly explained for nearly 25 years, Preston was shot in the arm in 1990, apparently by Sheen, and subsequently broke off their engagement.

But Sheen contradicted the story in 2011 (via TMZ), saying that Preston accidentally shot herself after dropping Sheen's revolver on the floor while emptying his trousers, Sheen naturally having a loaded gun absent-mindedly stuffed in his pocket.

The revolver discharged and hit a toilet, which then shattered and injured Preston.
It's... a little far-fetched, but Preston, now married to John Travolta and entrenched in Scientology, backed the story up soon after.

Seth MacFarlane and Emilia Clarke

The Family Guy creator and the Game of Thrones star dated for six months in 2013, with Clarke finally opening up about their relationship to Glamour Magazine in 2016.

Seth MacFarlane and actress Emilia Clarke in 2012. Photo / Getty
Seth MacFarlane and actress Emilia Clarke in 2012. Photo / Getty

When asked about the differences between dating someone in the public eye and dating someone unknown, she spoke of an unusual fan encounter:

"A con is you have strangers giving you love-life advice like, 'I'm a big fan of the show, and I'm not sure what you're doing with that guy,' which I didn't react well to.

"That happened in New York when Seth and I were together. This guy started to give me advice: "Can I get a selfie? And by the way..." Unh-unh, bro."

Ashton Kutcher and January Jones

It might sound a bit cheeky for Ashton Kutcher to impart acting advice on anyone, but he apparently tried to turn his one-time girlfriend and future Golden Globe nominee January Jones off acting.

Ashton Kutcher and January Jones in 1999. Photo / Getty
Ashton Kutcher and January Jones in 1999. Photo / Getty

"[He] was not supportive of my acting," she told GQ magazine. "He was like, 'I don't think you're going to be good at this.'

"He only has nice things to say now - if anything, I should thank him. Because the minute you tell me I can't do something, that's when I'm most motivated."

Jones later revealed on Andy Cohen's Watch What Happens Live that she didn't actually name Kutcher when recalling the story, but that the interviewer made an assumption of her ex-boyfriend's identity. However, when pressed by Cohen over whether it indeed was Kutcher, Jones remained mum.

Courtney Love and Edward Norton

Always a master of transformation, Courtney Love's post-Cobain metamorphosis into 'serious movie star' came complete with a respectable, educated and classy new boyfriend: Edward Norton.

Ed Norton & Courtney Love in 1998. Photo / Getty
Ed Norton & Courtney Love in 1998. Photo / Getty

"I had my movie-star moment," she told Bust. "I watched the VH1 special about me, Behind the Music, but the last half hour was an absolute wash. It was just like, 'Why didn't she marry Edward Norton and become a movie star?'

"I wasn't ready to, I didn't want to, I didn't know how to."

But while they were together for four years, and even got engaged, they seemed to have a somewhat volatile relationship. He read her private journals, infuriating her, and she also ditched him half-way up Ben Nevis to attend an Oasis concert after they had a fight.

Ten years after they split, she also embarked on a lengthy Twitter tirade against the actor, claiming he owed her $300,000.

Regardless, she still claims to owe him a debt of gratitude. She told Billboard in 2015: "I've got to give it up to Edward Norton for teaching me about acting and about philanthropy."

Steve Martin and Anne Heche

Before she embarked on an attention-grabbing relationship with Ellen DeGeneres, actress Anne Heche dated Steve Martin, who was 24 years her senior.

Steve Martin and Anne Heche. Photo / Getty
Steve Martin and Anne Heche. Photo / Getty

"I wanted the love of an older man," she told ABC News in 2000, following a very public breakdown in which she came to believe she was an alien named Celestia. "I wanted comfort. I wanted humor. I wanted all of the things that he offered. Why did we break up? There wasn't anything wrong with Steve. It was just that it was not what I wanted to commit my life to."

While it's not too wacky on paper, Martin later used Heche as his inspiration for one of his most memorable characters: the unbalanced, sexually manipulative and relentlessly ambitious young actress portrayed by Heather Graham in Martin's filmmaking satire Bowfinger, which he scripted.

Billy Corgan and Jessica Simpson

Billy Corgan sure knows how to pick 'em. The Smashing Pumpkins frontman not only briefly dated reality star turned celebrity Nazi Tila Tequila, but also had a brief fling with Jessica Simpson, notorious chicken-of-the-sea aficionado and office farter.

"If I go, 'Oh, we're just friends,' then it's like, 'Did they go out, did he dump her or she dump him, what happened?' It has nothing to do with any of that," he told Rolling Stone in 2010.

"Sometimes people just like being around each other, and good things come out of that. My goal in life is to love whoever I think is worth loving, and I think if people knew her like I knew her, they would love her like I do. It's really simple."

- Daily Telegraph UK

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