Some celebrity couples have seemed like a match made in heaven, while others have left us scratching our heads in confusion. Wonderwall.com is going back in time to look at some of Hollywood's most unexpected, out-of-left-field romances, starting with Ashton Kutcher and January Jones. The young couple began dating in 1998 when Ashton landed his breakout role on "That '70s Show." They lasted for three years before breaking up in 2001, reportedly because Ashton didn't support the future "Mad Men" star's acting ambitions. "He was like, 'I don't think you're going to be good at this.' So — f— you," January told GQ. "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." Keep reading to see other surprising celebrity hookups…
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That's right, Moby and Natalie Portman were once a thing. The singer shared during an interview in 2008 that he had a brief relationship with the "Black Swan" actress. "I guess in some people's eyes, [nerds] might be mildly sexy — and, as a nerd, I'm certainly happy to enjoy some of the effects of that," Moby said in 2008. "But as far as the very brief affair that I had with Natalie, it's made me a target of a lot of nerd wrath. You don't date Luke Skywalker's mom and not have them hate your guts."
Before Justin Timberlake settled down with Jessica Biel and before Jenna Dewan found love with now-ex-husband Channing Tatum, the two quietly dated. JT began seeing the "Step Up" actress, who was his backup dancer at the time, after splitting from Britney Spears. Jenna confirmed the long-rumored undercover love affair during an appearance on "Watch What Happens Live." "We dated. Not that long. We were like friends, then dated and we're just really good friends now," she told host Andy Cohen.
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Miranda Lambert shocked the world when, in February 2019, she confessed she'd secretly married New York City Department officer Brendan McLoughlin. Reports revealed that the country singer met the hot, younger cop in November 2018 around the time she performed on "Good Morning America," which has its studios in Times Square near Brendan's beat. It also emerged that a few days after Brendan met Miranda, he welcomed a baby with another woman — a lawyer he allegedly got pregnant while he was engaged to a professional soccer star who quickly dumped him when she found out.
A young '80s love! Before they were A-list superstars, Christian Bale and Drew Barrymore briefly went out as teens. The pair went on one date together — and it didn't go well, Christian admitted. "We went to see some bloody awful horror film, and that was the end of it," the "Vice" star told GQ Australia. "She never called again."
Julie Bowen and David Spade were once hot and heavy. The "Modern Family" star and the comedian, who are pictured here at the "Punch-Drunk Love" premiere, had a short-lived relationship back in 2002. The two eventually went their separate ways and found love elsewhere: Julie married now-ex-husband Scott Phillips in 2004 and David went on to date other beautiful blonde actresses like Nicollette Sheridan.
We definitely didn't see this one coming! Heidi Klum's ex, singer Seal, and Tyra Banks were an item back in 1996. The couple made their first and only public appearance together at the Essence Awards in New York City before calling it quits.
Back in the 1980s, Jon Bon Jovi and Diane Lane were one of Hollywood's newest and hottest couples. The twosome only dated for five months, but the relationship was one that had a lasting impact on Diane. "I think every girl should have such a wonderful experience when she's that young," the "Unfaithful" star said on "Watch What Happens Live." She also commented on some old-school pictures she has of Jon, saying "I have some photos of him packing for the tour. Just all the jockstraps were lined up on the floor for the whole band to get through the whole tour. You have to under those leather pants, sweating!"
Fans were shocked when actress Cameron Diaz, the quintessential California beach girl, and tattooed Good Charlotte rocker Benji Madden got together. Sparks flew after the pair were introduced by Benji's sister-in-law, Nicole Richie (who's married to his twin brother, Joel Madden), in 2014. The couple got engaged seven months later and married only 15 days after that! "I think it's a matter of I just hadn't met my husband, you know? I had boyfriends before. And there's a really, really distinct difference between husbands and boyfriends," Cameron said during a Goop panel discussion when asked why she waited until 41 to get married. "And I have a husband who is just my partner in life and in everything. Talk about two very different people! We are so different from one another, but we share the same values — we're totally two peas in a pod. We are both just weird enough for each other."
Long before she was Mrs. Chris Hemsworth, Elsa Pataky was head over heels for Adrien Brody. The Spanish actress and the Oscar winner began dating in 2006 and were so serious that Adrien bought Elsa a 19th-century castle in upstate New York for her 31st birthday! Alas, it wasn't meant to be and the couple broke up in 2009.
Shia LaBeouf and Rihanna might be the most random celeb pairing ever! The "Transformers" actor and the Bajan beauty reportedly went on one date in 2007 but Shia told Playboy that "the spark wasn't there."
When Renee Zellweger and Kenny Chesney appeared on the cover of People magazine to announce their marriage, fans were surprised, to say the least. The unlikely pair wed in May 2005 after about four months of dating. The Oscar winner then filed for an annulment four months after that, citing "fraud." The marriage was so quick that Renee told The Advocate in 2016 that she forgot it ever took place! "I forgot about that," she said. "It's a pretty big thing to forget, isn't it?"
The celebrity romance nobody saw coming (literally, nobody)! Once upon a time, Tom Cruise and Cher were caught up in the throes of love. The pair dated in 1987 when Tom was just getting started in the industry. During an interview with Bravo's Andy Cohen decades later, Cher said she was "crazy" for the "Top Gun" actor, whom she described as "shy." But she also said he was in "the top five" on her list of best lovers.
When country music star Lyle Lovett and "Pretty Woman" actress Julia Roberts eloped in 1993 after just three weeks of dating, Hollywood — and their fans — were shocked! Their busy schedules kept them apart, however, and the couple parted ways less than two years later.
Before Kim Kardashian West was the makeup mogul and reality TV star she is today, she was an up-and-coming socialite who was interested in Nick Lachey. The two dated briefly in the early 2000s but soon called it quits in part because Kim was too interested in becoming famous. "Let's just say this: We went to a movie. No one followed us there. Somehow — mysteriously — when we left, there were 30 photographers waiting outside," Nick told Details in 2013.
Brad Pitt has dated his fair share of lovely ladies over the years (Jennifer Aniston, Gwyneth Paltrow, Robin Givens, Juliette Lewis), but did you know that he once romanced Sinitta? The actor and the singer — who's best known in Britain (she famously also dated Simon Cowell!) — shared a two-year relationship in the late '80s, but eventually ended things due to distance. "I'd go over quite a lot but, at the end of the day, you want someone you can hang out with, not someone you're always waiting for," Sinitta told the Sunday Express of Brad, whom she said was "just a very cute boy" during their love affair.
Kristen Bell is well-known for her loving marriage to Dax Shepard, but she once had a college fling with former "Glee" star Matthew Morrison. "I actually went to college with Matty Morrison. We actually dated very briefly, so I'll have to say maybe Matt Morrison is my favorite part of 'Glee' for various reasons," Kristen revealed to Us Weekly.
A Malibu reality TV star and a Canadian pop-punk singer? What could be better! Avril Lavigne and Brody Jenner somehow found love in 2010 and dated for nearly two years before splitting in 2012. "Avril and I are still friends who talk, and I wish her nothing but the best… she's a great girl," Brody told the Huffington Post after their breakup.
We know, we know — it's unbelievable, right? But it's true! Madonna romanced the late Tupac Shakur during the '90s. Rosie Perez introduced the unlikely pair at the Soul Train Awards in 1993 and sparks flew. "I was dating Tupac Shakur at the time and the thing is, he got me all riled up about life in general," Madonna reflected to Howard Stern about that time. A breakup love letter the rapper wrote Madonna in the '90s surfaced in 2018. "First and foremost, I must apologize to you because like you said, I haven't been the kind of friend I know I am capable of being," the hip-hop star wrote in the first half of the letter.
Today, Ryan Reynolds and Melissa Joan Hart both have adorable families with their respective spouses, Blake Lively and Mark Wilkerson, but once upon a time, they shared a teen romance. Melissa reflected on one particular hot-and-heavy session after Ryan gifted her with a Beluga watch, writing about the date in her memoir "Melissa Explains It All: Tales from My Abnormally Normal Life." "He was 17 and I was, like, 19. I was like, 'You're too young for me.' So I stopped his car … and I wasn't sure; am I gonna get mad at him? I wasn't sure so I just grabbed him and started kissing him. You get a piece of jewelry like that, you gotta make out with the guy," she wrote.
Fans were completely thrown when shock-rocker Marilyn Manson began dating girl-next-door actress Evan Rachel Wood in 2007. Not only did the two have vastly different images, but they were also years apart in age (at the time, Manson was 34 and Evan was 19). Nevertheless, their love persisted for a number of years and the two eventually got engaged before parting ways in 2010.
Drew Barrymore and David Arquette had a love affair in the early '90s — a few years before they played brother and sister in "Never Been Kissed." "[Drew and I] used to date when we were very young kids. Well, not little kids!" David told the Daily Mail. "She's just one of the sweetest, kindest people in Hollywood. She always has been, and she always will be. She's just a lovely, sweet person. We used to run around and just be silly."
Owen Wilson and Sheryl Crow were once one of Hollywood's hottest — and most unexpected — couples. The Texan actor and the Missouri-born musician had a three-year relationship in the early 2000s — Sheryl even dedicated her 2002 song "Safe And Sound" to Owen. They were broken up by 2003 but the singer still referred to Owen as "so talented, and a great, great person" in an interview with The Associated Press.