Jon Lovitz And Jessica Lowndes
[ranking: 1]
When she was 27, 90210 actress Jessica Lowndes revealed that she was dating 58-year-old comedian and actor Jon Lovitz in the spring of 2016. Days later, however, she revealed it was all a hoax.
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Courtney Stodden And Doug Hutchison
[ranking: 2]
Doug Hutchison wasn??t much of a celebrity until he married a 16-year-old virgin. The character actor met the highly ambitious Courtney Stodden, 35 years his junior, online. After a bit of a courtship, her parents gave the actor consent to marry their daughter. Stodden and Hutchison wed in 2011. They split up in 2013 due to their age gap, but it didn??t last long. They got engaged in 2014, with Stodden saying that she had given other men a try and missed her husband.
Besides the age thing, it was Stodden??s hilarious behavior during an ABC interview that went viral. Stodden??s dad is four years younger than Hutchison.
Mary-Kate Olsen And Olivier Sarkozy
[ranking: 3]
When former Full House darling Mary-Kate Olsen was seen cozying up to the brother of the former president of France, people balked. The two seemingly come from different worlds and the 17-year age difference made this odd celebrity couple even stranger.
The French banker and the actress-turned-fashion designer married in 2015.
Jennifer Aniston And Adam Duritz
[ranking: 4]
This odd couple is even odder now. Jennifer Aniston was a hot star in 1995, thanks to Friends, and Counting Crows was a big-time band. Adam Duritz dated Aniston??s Friends costar and bestie Courteney Cox right after.
Duritz defended this move by saying, ??[Aniston and I] never even slept together.??
Courteney Cox And Adam Duritz
[ranking: 5]
The news of their relationship was met with a lot of head scratching back in 1997. The Friends star appeared in the Counting Crows video for ??A Long December,?? causing music fans and TV fans to consider a whole new dating pool.
Considering Adam Duritz also dated Jennifer Aniston and Emmy Rossum, it??s strange to know that he would end up on Tinder in 2014, having not yet found "the one."
Bill Murray And Jenny Lewis
[ranking: 6]
A Page Six report in 2015 seemed to indicate actor Bill Murray was dating indie rocker Jenny Lewis. The two were reportedly seen together at the after party for Murray's 2015 film Rock the Kasbah.
Other sources said that the two were just friends, but it would be awesome if the rumors were true!
Evan Rachel Wood And Marilyn Manson
[ranking: 7]
She was 19. He was 36. ??People were pretty mean," Wood told The Daily Beast. "At the time I hadn??t yet been exposed to that kind of cruelty from strangers." The actress later married Jamie Bell and started a family.
??If people were wondering why I was acting so-called crazy or like a teenager, it??s because I was,?? she said. ??People go through phases. People make mistakes. People go through life and don??t get it right every time.??
Jerry Hall And Rupert Murdoch
[ranking: 8]
Jerry Hall and Rupert Murdoch got married in 2016. They were 59 and 84, respectively. It's Murdoch's fourth marriage, but it's technically Hall's first, as her marriage to Mick Jagger from 1990 to 1999 was declared void by the British government.
Hall and Murdoch were first seen together at the 2015 Rugby World Cup Final between Australia and New Zealand.
Roger Ebert And Oprah Winfrey
[ranking: 9]
Their two dates didn??t turn into a long-term relationship but they did make Oprah the reigning queen of daytime TV and a living legend. Ebert recounted how he advised her on taking a deal with either ABC or King World. On their date at Hamburger Hamlet, Ebert did some simple math and showed Winfrey just how much a syndication deal with King World would make her.
She made up her mind in 10 seconds: ??I??m going with King World.?? They may not have waltzed down the aisle, but we do have Ebert to thank, in part, for Oprah.
Billy Corgan And Jessica Simpson
[ranking: 10]
Jessica Simpson asked Smashing Pumpkins frontman Billy Corgan to help her with the theme song for The Price of Beauty because... who knows? Then E! News suggested they were an official couple. Corgan, however, told the Chicago Tribune: "The stuff that I've seen doesn't have any bearing to the reality that I'm in. It's like being in a cartoon. It has nothing to do with what's really going on or how I feel."
While she was said to be dating Corgan, Simpson told Allure: "I definitely will marry an artistic man. I don't have a physical type. I have an emotional type. When you have yourself together, I don't care what you look like at all." Was that a backhanded compliment to Corgan?
Chelsea Handler And 50 Cent
[ranking: 11]
This strange celebrity couple dated in 2010. Handler met the Queens native on her show Chelsea Lately. They immediately connected and flirted, even with her love for vodka and his famed sobriety.
They continue to flirt on social media, so there seems to be a lot of healthy feelings still lingering.
Aaron Taylor-Johnson And Sam Taylor-Johnson
[ranking: 12]
Aaron Taylor-Johnson and Sam Taylor-Johnson got engaged when the Kick-Ass star was 19 and the director was 43 and pregnant with Johnson??s child. The 24-year gap didn??t seem to register with the couple, who met on Taylor-Wood's directorial debut Nowhere Boy.
"The amount of men I know with the same age gap [with younger women] that we have - how come no one says anything about that?" she said in 2010. "It's totally sexist. I try to ignore it."
Courtney Love And Edward Norton
[ranking: 13]
In a ??Huh??? heard round the world, the stars of The People vs. Larry Flynt dated from 1996 to 1999 and even got engaged. Courtney Love gave up smoking for Edward Norton as part of an attempt to live a healthier lifestyle.
Love called Norton a "force of good" in her relationship with her daughter.
Billy Corgan And Tila Tequila
[ranking: 14]
Dubbed ??random?? by Digital Spy, Billy Corgan and Tila Tequila dated briefly in 2009, attending Bravo's A-List Awards together.
Seth MacFarlane And Amanda Bynes
[ranking: 15]
In 2008, Family Guy creator Seth MacFarlane and actress Amanda Bynes allegedly dated. Their 12-year age difference is the least strange thing about this odd duo.
Rosario Dawson And Danny Boyle
[ranking: 16]
Both delightful and odd, this famous couple was completely unexpected due to a 23-year age difference and Rosario Dawson??s penchant for dating hunky types. So the pair caused quite a stir when they made their relationship public.
In 2013, she confirmed that the pair had split: "It's not like we announced our relationship, so it's not like we're going to announce our breakup. I love Danny. He's wonderful and we dated longer than people think we did."
Mila Kunis And Macaulay Culkin
[ranking: 17]
When Mila Kunis and Macaulay Culkin first emerged as a couple in the aughts, they raised more than a few eyebrows. Culkin??s career seemed to be over and Kunis??s star was about to rise. Kunis was a breath of fresh air in Culkin??s life and they spent eight years together.
While they dated in 2009, Kunis revealed that marriage wasn??t for her: ??Not to say that I don't believe in it, but it's just not something that's important to me. But I will have children. I'm too selfish to have them now, but when I do, I don't feel like I need to be married.??
The couple split in 2013, and she married Ashton Kutcher in 2015.
Kate Beckinsale and Pete Davidson
[ranking: 18]
Kate Beckinsale, 45, and Saturday Night Live star Pete Davidson, 25, were first spotted at Netflix's Golden Globes after party in January 2019. The following few months they were spotted hand-in-hand at Pete Davidson's comedy shows as well as a hockey game at Madison Square Garden in New York City.
Underworld star Kate Beckinsale and Pete Davidson gained attention for their age difference and their inability to resist packing on the PDA. Pete Davidson finally addressed the new relationship on "Weekend Update" on Saturday Night Live.
However, the relationship has reportedly fizzled out due to the distance, with People reporting that Kate Beckinsale and Pete Davidson have since split, ending nearly four months of dating.
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Ashley Olsen And Lance Armstrong
[ranking: 19]
Before Lance Armstrong??s doping scandal, he had an image to maintain. Armstrong??s friend and the head of the Livestrong Foundation, John Korioth, strongly encouraged the cyclist, 36 at the time, to drop his relationship with then-21-year-old Ashley Olsen to protect his image.
In her book Cycle of Lies, Juliet Macur recounted Korioth's telling Armstrong: ??Whoa, dude, bad idea. You??ve got to put a stop to this right now.??
Armstrong reportedly responded, ??She??s 21... f*ck you.?? The relationship ended pretty quickly after it started.
Drew Barrymore And Tom Green
[ranking: 20]
Tom Green was the awkward Canadian comedian with a prank show. She was a young actress who seemed to be trying on different lives. Barrymore would marry others for briefer periods but the choice of Green was out of left field, even for her.
They married in 2001 and lasted nine months. Green called that moment in his life ??a crazy, whirlwind of a time.??
Renee Zellweger And Jack White
[ranking: 21]
This duo rates as one of those odd celebrity couples because it??s hard to imagine either of them moving in the other??s circle. They reportedly dated for a year and a half before splitting in 2004.
Moby And Natalie Portman
[ranking: 22]
This pair briefly dated in 2001, and Natalie Portman??s fandom was not happy about it. This was not the droid they were looking for. In a Spin interview, Moby shed some light on how people reacted to the relationship.
??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 - but as far as the very brief affair I had with Natalie, it??s made me the target of a lot of nerd wrath," he said. "You can??t date Luke Skywalker??s mom and not have them hate your guts.??
Ryan Reynolds And Kristen Johnston
[ranking: 23]
Ryan Reynolds dated Kristen Johnston in 1999. The 3rd Rock from the Sun actress had more street cred than him at the time.
Nick Jonas And Priyanka Chopra
[ranking: 24]
In May 2018, rumors circulated that Nick Jonas and Priyanka Chopra - who is 10 years Jonas's senior - were dating. Fans found photos of the two relaxing together with friends during Memorial Day weekend and even attending a Dodgers game.
The two got engaged in July 2018. They wed later that year.
Nicki Minaj And Eminem
[ranking: 25]
In May 2018, Nicki Minaj suggested she was dating Eminem, 10 years her senior, in an Instagram post. Both rappers fueled rumors they were dating throughout the year, sometimes confirming them and sometimes denying them.
Sandra Bullock And Jesse James
[ranking: 26]
The motorcycle builder met America??s sweetheart in 2005 when she took her godson to visit Monster Garage. The highly unlikely couple immediately began dating and then married. Jesse James infamously cheated on Sandra Bullock, which ended their five-year marriage, made a lot of fans say ??I told you so, Sandy!?? and made James the ultimate villain.
He apologized to Bullock but later blamed the downfall of his career on their marriage.
Adrienne Maloof And Sean Stewart
[ranking: 27]
Reality star Adrienne Maloof divorced Paul Nassif in 2012. She then dated Sean Stewart, Rod Stewart??s son, who is 19 years younger than she is. But after a while, the shine wore off. An insider told Radar, ??She basically said, ??I already have kids, I don??t need another one.????
She moved on to Anheuser-Busch heir Jacob Busch in 2013, when she was 52 and he was 24.
Ashton Kutcher And Demi Moore
[ranking: 28]
Demi Moore was 16 years Ashton Kutchar's senior when they got together in 2003. The unusual pairing worked quite well for eight years. Kutcher and his That ??70s Show costar Mila Kunis later made Jackie and Kelso a thing in real life.
Michelle Rodriguez And Zac Efron
[ranking: 29]
Michelle Rodriguez hooked up with Zac Efron in 2014 soon after she split with model Cara Delevingne. When Efron and Rodriguez appeared to be an item, the world had a meltdown with every major media outlet doing a collective double take.
Then, there was a huge wave of support, when media and fans alike were rooting for the couple. But it didn??t last.
Ryan Reynolds And Alanis Morissette
[ranking: 30]
Isn??t it ironic? Doncha think? Ryan Reynolds seems to have a type and Alanis Morissette refreshingly didn??t fit his later Scarlett Johansson/Blake Lively profile. Fans and media outlets couldn??t quite wrap their heads around the A-list actor and the more-popular-in-the-'90s singer getting engaged in 2004.
This was no fly-by-night celebrity couple, though. They stayed together for five years. Morissette said her 2008 album Flavors of Entanglement was inspired by the break-up.
Katie Holmes And Jamie Foxx
[ranking: 31]
Dawson's Creek star Katie Holmes and Django Unchained star Jamie Foxx began dating under the radar in 2013. In 2015, Holmes was caught wearing a disguise to meet Foxx at a hotel. They had been caught by paparazzi holding hands years earlier, and sources said their friends and family knew about the relationship.
But the two had yet to go public when Holmes was spotted in a wig in September 2015.
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Lisa Kudrow And Conan O??Brien
[ranking: 32]
Conan O'Brien was a writer for Saturday Night Live and Lisa Kudrow was a comedian in Los Angeles. Their larger-than-life kooky personalities seem like an odd match now, but at the time, they had a lot in common.
??He was really smart, really funny and he thought I was funny," Kudrow said, adding the two "found we were better as friends."
Kim Kardashian And Nick Cannon
[ranking: 33]
From 2006 to 2007, before Kim Kardashian nailed her look and before Nick Cannon was Mr. Mariah Carey, these two were one of the stranger celebrity couples. Cannon said he dumped Kardashian because she denied the existence of that tape. You know, the one that made her famous.
"She??s actually one of the nicest people you??ll ever meet," he said in 2012. "But the fact that she lied and told me that there was no tape?"
Katy Perry And Russell Brand
[ranking: 34]
People are still wondering how this strange celebrity pairing even happened. Katy Perry??s career was founded on 100% sugary girl power. Russell Brand is hellbent on shaking everyone up. She was a Christian singer. He??s a former addict.
Somehow they clicked. But after 14 months of marriage, he sent her a text saying that he was filing for divorce. The perpetually touring Perry received the text during rehearsals, out on the road.
David Spade And Julie Bowen
[ranking: 35]
Apparently, David Spade has serious game. He??s dated Heather Locklear, Nicolette Sheridan, Lara Flynn Boyle, and Pamela Anderson, and he has a child with former Playboy playmate Jillian Grace. He dated Julie Bowen in 2002.
Jennifer Lawrence And Chris Martin
[ranking: 36]
People didn??t like the age difference - 13 years - and they didn??t like their favorite opinionated actress dating mellow Chris Martin. Also... Coldplay. Still, every major Hollywood outlet lost their minds when these two began dating after the conscious uncoupling of Martin and Gwyneth Paltrow.
The couple broke up in 2015. Jennifer Lawrence's friend reportedly told People the actress got ??tired of Chris being so noncommittal.??
Hayden Panettiere And Wladimir Klitschko
[ranking: 37]
This odd celebrity couple was met with a lot of noise about their height difference - she??s 5?? 2?? and he??s 6?? 6?? - as well as why the actress would choose heavyweight boxing champion Wladimir Klitschko as her boo. For Hayden Panettiere, it was a no-brainer.
"I know that I'm small, but he's large," she said in 2013, the year they got engaged. "That's how we met. I said, 'You're huge.' He said, 'You're tiny.'" The pair broke off their engagement in 2018.
Benji Madden And Cameron Diaz
[ranking: 38]
Many media outlets thought this was an odd pairing. Cameron Diaz is only six years older, but most bookies wouldn??t have put these two together. Guess who did? Nicole Richie.
Richie is married to Benji Madden??s twin brother Joel, and she set Diaz and Madden up.
Courteney Cox And Michael Keaton
[ranking: 39]
Remember that time Michael Keaton dated Courteney Cox for six years until they broke up in 1995? No one else does either. The two were close but didn??t seem like an obvious choice to their respective fan bases. Something clicked because six years is a long time and they only ever said good things about each other.
"It's the most important relationship I've ever had, and I think he's the most wonderful person I've ever met,?? Cox said after they split up.
Owen Wilson And Sheryl Crow
[ranking: 40]
Once upon a time, Hollywood made a movie called The Minus Man. This is where Owen Wilson met Sheryl Crow. Their relationship was met with a ??What?!?? from the media at large, but the two Texans dated from 1999 to 2001.
Crow went on to date Lance Armstrong, who would later date Wilson??s ex, Kate Hudson.
Avril Lavigne And Brody Jenner
[ranking: 41]
She??s the rebellious singer. He??s the boy next door. Avril Lavigne??s other partners, husbands Deryck Whibley from Sum 41 and Nickelback's Chad Kroeger, seem far afield from Brody Jenner. If this were a John Hughes movie, they??d be natural enemies, but the odd celebrity couple had a two-year run before calling it quits.
Ashton Kutcher And January Jones
[ranking: 42]
Before January Jones was Betty Draper on Mad Men, and while Ashton Kutcher was Michael Kelso on That '70s Show, the pair dated in 2000.
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