By Marisa Laudadio
6:36am PDT, Mar 17, 2015
Opposites attract — until they don't. With huge differences in age, looks, careers or social circles, all of these couples made headlines when they hooked up because they just seemed so oddly matched — so it was no surprise when their relationships eventually imploded. Join us as we revisit these unusual couples, starting with Cher and Tom Cruise. That's right — they actually dated. Cher was 16 years older than Tom when they got together in the mid-'80s. "He was so wonderful. And I was so crazy about him," Cher told Oprah Winfrey in 2008. "He was a shy boy. He didn't have any money." During a 2013 appearance on "Watch What Happens Live," Cher opened up even more. "He wasn't a Scientologist then," she added. But how did he rank on her all-time lovers list? Said Cher: "He was in the top five!" Weird, right?! Keep clicking for more …
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Whoopi Goldberg and Ted Danson
Whoopi Goldberg and Ted Danson fell for one another while co-starring in "Made in America" in 1992. Their affair led him to divorce his wife, producer Casey Coates, the following year, but he and Whoopi didn't last. In 1995, Ted married actress Mary Steenburgen.
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Julia Roberts and Lyle Lovett
Beautiful acting ingenue Julia Roberts and offbeat country singer Lyle Lovett, who was a decade older, tied the knot in 1993 just three weeks after they met. But they were often separated by their work and just 21 months later, they announced their marriage was over.
David Gallagher and Megan Fox
So maybe this pairing wasn't weird at the time, but it sure seems surprising now: Megan Fox was just 17 and starring in her very first movie, "Confessions of a Teenage Drama Queen," when she stepped out at the film's 2004 premiere with boyfriend David Gallagher, then 19 and the star of the hit show "7th Heaven." The young lovers split later that year.
Andre Agassi and Barbra Streisand
It was classic cougar: When world-famous movie star and award-winning singer Barbra Streisand started showing up courtside to support red-hot tennis champ Andre Agassi at his matches in the early '90s, the world learned they were dating, 28-year age difference be damned. But their romance ended in 1993, the same year he started seeing now ex-wife Brooke Shields.
Michelle Rodriguez and Zac Efron
When Zac Efron and Michelle Rodriguez were photographed all over Europe in the summer of 2014 engaging in serious PDA, their pairing raised eyebrows — in part because Michelle was nearly a decade older than the former Disney star, but mostly because her last relationship was with a woman (that would be supermodel Cara Delevingne). But after just two months, Zac and Michelle's summer fling flamed out.
Cameron Diaz and Diddy
If Cameron Diaz's marriage to tattooed Good Charlotte rocker Benji Madden in January 2015 wasn't surprising enough, there's this: She and rap mogul Sean "Diddy" Combs used to hook up from 2008 to 2012. According to Us Weekly, Diddy — who was spotted making out with the blonde beauty multiple times in 2011 — lamented to friends during a 2014 dinner that fun-loving Cameron is the one that got away. "He said, 'If I could turn back time, things would be different,'" a source told the magazine.
Adrienne Maloof and Sean Stewart
Two months after divorcing plastic surgeon Paul Nassif, reality star Adrienne Maloof got herself a younger man — 19 years younger, to be exact. The former "The Real Housewives of Beverly Hills" cast member and Rod Stewart's son Sean Stewart went public with their unconventional romance in January 2013, but two months later, they decided they made better friends than lovers. Still, Adrienne has no regrets. "Age is just a number," she told TMZ. "It's about how good of a person you are."
Evan Rachel Wood and Marilyn Manson
Evan Rachel Wood was just 19 when she started dating shock-rocker Marilyn Manson, who was 17 years her senior and still married to burlesque star Dita Von Teese. After a brief split, Evan and Marilyn reconciled and got engaged — only to break up for good in 2010. "People go through phases. People make mistakes. People go through life and don't get it right every time," she told The Daily Beast of her wild former romance.
Oprah Winfrey and Roger Ebert
Legendary TV and Chicago Sun-Times film critic Roger Ebert and his wife, attorney Chaz Hammelsmith, were happily married for more than two decades until his death from cancer in 2013. Which is one reason the world was so shocked when he and Oprah Winfrey revealed on her 20th anniversary show that they'd dated in the '80s. During one of their two dates, over dinner at Hamburger Hamlet (his treat), Roger encouraged Oprah to take a lucrative syndication deal for her eponymous show — and the rest is history.
Jennifer Love Hewitt and Jamie Kennedy
When Jennifer Love Hewitt and her "Ghost Whisperer" co-star Jamie Kennedy, 11 years her senior, went public with their relationship in 2009, many fans were left scratching their heads. What was a beautiful, voluptuous actress like her doing with a goofy comedian like him? But the actress was undeterred. "There are people in your life who are just supportive and who just look at you and they see who you are," she told Ellen DeGeneres, "and [Jamie] really saw who I was as a person more than anybody had ever done in my whole life. I think that's for me when I sort of went, 'Oh, wow.'" But by 2010, the naysayers won out, and the couple quietly split.
Richie Sambora and Cher
Tom Cruise isn't the only famous younger man who's been romanced by Cher. In the late '80s and early '90s, she dated equally style-challenged star Richie Sambora, who's 13 years her junior. The Bon Jovi guitarist, who has a fashion line called White Trash Beautiful, later credited the icon for influencing his fashion sense. "A turning point for me was when I was about 28 years old and I started dating Cher. Obviously she's a fashionista, she taught me a lot," Richie told Racked in 2011. "How to put things together. You shouldn't wear this with that; what was right for the occasion. Because when you're a kid, you don't know that kind of stuff, especially when you're a man. She's a great lady."
Kenny Chesney and Renee Zellweger
Barely four months after meeting at the Concert of Hope tsunami relief benefit in January 2005, Oscar winner Renee Zellweger and country crooner Kenny Chesney got married on a tropical island before most people realized they'd even been dating. But just a few months later, it was over, with Renee famously citing "fraud" in papers seeking to annul their marriage, which left Kenny fending off rumors that he was gay. "What guy who loves girls wouldn't be angry about that s—?" Kenny told Playboy a few years later. "I think people need to live their lives the way they want to, but I'm pretty confident in the fact that I love girls. I've got a long line of girls who could testify that I am not gay."
Renee Zellweger and Jack White
Before marrying Kenny Chesney, Renee Zellweger enjoyed an on-off and eyebrow-raising romance with quirky indie musician Jack White after they met on the set of "Cold Mountain" in 2002. But by 2004, the petite actress' love affair with the hulking 6'2″ White Stripes frontman was dunzo.
Brooke Shields and Michael Jackson
Brooke Shields and Michael Jackson's relationship was an odd one. Devoid of sexual intimacy, the pair — both former child stars — would hold hands during their unusual courtship in the early '80s, but after the King of Pop's death in 2009, Brooke revealed they were more friends than anything else. But that doesn't mean Michael didn't love her. "There were times when he would ask me to marry him, and I would say, 'You have me for the rest of your life, you don't need to marry me, I'm going to go on and do my own life and have my own marriage and my own kids, and you'll always have me.' I think it made him relax," she told Rolling Stone.
Lisa Marie Michael Jackson
Even weirder than Michael Jackson's marriage proposals to Brooke Shields? His quickie wedding with Lisa Marie Presley. Three months after her split from first husband Danny Keough, Elvis' only child married the King of Pop in 1994 at a judge's home in the Dominican Republic. They kissed on stage at the MTV Video Music Awards later that year then stripped down for his "You Are Not Alone" video in 1995, but by 1996, Lisa Marie had filed for divorce.
Vanilla Ice and Madonna
For eight months, Madonna dated rapper Vanilla Ice — until he dumped her in 1991. "She was [nine years] older than me and a great lover," he told News of the World. "But I broke up with her after she printed that book [Sex] because I was hurt to be an unwitting part of this slutty package." Ouch!
Madonna and Dennis Rodman
After Vanilla Ice but before Carlos Leon — the father of her daughter Lourdes Leon — there was Dennis Rodman. Madonna dated the basketball bad boy for a few months in the early '90s. "I didn't know what the hell this white megastar wanted from me," Dennis wrote in his autobiography — then claimed she'd begged him to get her pregnant.
Kimberly Stewart and Benicio del Toro
By the time the world found out that Oscar winner Benicio del Toro and Rod Stewart's daughter Kimberly Stewart had dated, they'd already broken up. But their hookup news was shocking for another reason — and it wasn't because he's 12 years older than the former model. "Kimberly is pregnant. Benicio is the father and is very supportive," his rep told Life & Style in April 2011. "Although they are not a couple, they are looking forward to the arrival of the baby." Kimberly gave birth to baby Delilah less than four months later.
Simon Cowell and Carmen Electra
A few months after they were photographed together in the fall of 2012, Simon Cowell finally confirmed he was seeing gorgeous Carmen Electra — but admitted they weren't exclusive. "We're people who date. She's adorable, isn't she?" the British music executive told Ryan Seacrest of the star who's 13 years his junior. Carmen, however, played down their romance when Billy Bush asked if they'd "kissed" and "been in a horizontal situation." Her reply: "Maybe!" A few months later, they'd gone their separate ways.
Courtney Love and Steve Coogan
Courtney Love doesn't have fond memories of her brief 2005 romance with British comedy star Steve Coogan. "That was a two-week fling and we didn't even exchange numbers at the end of it," she told the U.K.'s Sunday Times Magazine of her dalliance with the "I'm Alan Partridge" star, who is, like her, a former addict. "That was my last dance with cocaine."
Doug Hutchison and Courtney Stodden
The world was floored when "The Green Mile" actor Doug Hutchison married 16-year-old wannabe singer Courtney Stodden in 2011. Despite their 35-year age difference, they managed to stay together for two and a half years while attempting to forge careers as reality stars. Then Courtney filed for legal separation. But this one does have a happy ending — sort of: In August 2014, Courtney changed her mind and the pair reconciled — at least for the time being.
