Out of their league: Ugly guys who date bombshells
How do these odd-looking guys attract such lovely ladies?
Ashley Olsen and Richard Sachs
Corey Feldman and Courtney Anne
Corey Feldman proudly walked the red carpet with his fiancee who is 18 years younger than he is. The couple, who dated for four years, said they plan to tie the knot quickly because Feldman has fears his Canadian lady might get deported.
Mel Gibson and Rosalind Ross
Mel Gibson proudly walked the red carpet with his 26-year-old girlfriend Rosalind Ross who will welcome his ninth child in several months. The mismatched duo have been together for two years.
David Hasselhoff and Hayley Roberts
Kirsten Dunst and Jesse Plemons
Rumor has it that stunning actress Kirsten Dunst is dating her “Fargo” co-star Jesse Plemons. Good for him!
Paul McCartney Nancy Shevell
Ronnie Wood and Sally Humphreys
Josh Brolin and Kathryn Boyd
Third time’s the charm? Josh Brolin walked the red carpet at the LA premiere of “Everest” with his fiancée Kathryn Boyd by his side. This will be the third marriage for the actor who was previously married to Alice Adair and Diane Lane. Brolin met the former model when she was his personal assistant. While Brolin’s certainly not a bad catch, Boyd is clearly his better half.
Flavio Briatore and Elisabetta Gregoraci
Christina Milian and Lil Wayne
Christina Milian and rapper Lil Wayne have been linked since the summer after Milian split from fiance Jas Prince. The two connected after working together in the studio. This isn’t the first time Milian has found love through music. Her ex-husband The Dream was her producer before the divorced in 2011.
Gabrielle Anwar and Shareef Malnik
Harvey Weinstein and Georgina Chapman
Harvey Weinstein is married to Marchesa designer Georgina Chapman. The nearly 24-years age difference doesn’t seem to phase this couple; they have two children together.
Mickey Rourke and Anastassija Makarenko
Mickey Rourke and his much younger and better half model Anastassija Makarenko have been dating for four years. Rourke, who has been looking worse for wear these past few years, is one lucky guy to call the Russian beauty his girlfriend.
Marc Anthony and Shannon De Lima
Marc Anthony reportedly popped the question to his model girlfriend Shannon De Lima and she said yes! De Lima adds to the already long list of lovely ladies Anthony has been able to woo including Jennifer Lopez.
Salma Hayek and Francois Pinault
Kristen Bell and Dax Shepard
Seth Green and Clare Grant
Seth Green definitely has a better half. The 40-year-old has been married to actress Clare Grant since 2010. The couple worked together on “Robot Chicken” and “Warren the Ape.”
Robert Duvall and Luciana Pedraza
Actor Robert Duvall and his wife Luciana Pedraza are exactly 41 years apart. Duvall and his Argentine actress wife share the same birthday give or take a few years. Pedraza, the “MASH” actor’s fourth wife, has been married to Duvall since 2005.
Jason Aldean and Brittany Kerr
Mary-Kate Olsen and Olivier Sarkozy
David Cross and Amber Tamblyn
The “Two and a Half Men” actress married funnyman David Cross when she was 29 and he was 48. Years later, the couple are still going strong. Tambyln clearly wanted a guy with a good sense of humor.
Cameron Diaz and Benji Madden
We’re not sure why Cameron is mad about Madden. “The Other Woman” actress and the Good Charlotte rocker married in 2015.
Christina Hendricks and Geoffrey Arend
While most look at this happily-married couple and ask, “How did he land her?” Hendricks has called Arend “the best husband ever.” “He’s just so old-fashioned and kind and dreamy,” the “Mad Men” actress told the Daily Mail. To each their own?
Padma Lakshmi and Salman Rushdie
Lakshmi was introduced to author Salman Rushdie at a 1999 party and the couple were married in 2004. The union didn’t last very long and the two divorced in 2007. She is said to be the muse for many of Rushdie’s writings.
Olivia Wilde and Salman Rushdie
Rushdie has a knack for wooing beautiful women. The author was also linked to actress Olivia Wilde.
Katy Perry and Travis McCoy
Beautiful, bubbly Katy Perry knows how to create catchy pop tunes and wow us with quirky-sexy outfits, but her choice in men is questionable. As if marrying Russell Brand wasn’t bad enough, she also dated “Gym Class Heroes” singer Travis McCoy. Katy likes her men rough around the edges… to put it nicely.
Heidi Klum and Seal
Heidi and Seal were a Hollywood golden couple for seven years before they ended things in 2012. (That’s like 37 years in Hollywood time.) And while Seal does have the voice of an angel, his looks don’t quite stack up to those of his stunning model ex-wife. She did publicly talk about his “package” during their years together, but hey, maybe she also liked his personality.
Malin Akerman and Roberto Zincone
This pair met in 2003 when they were part of the same band, “The Petalstones,” and while they both may have musical talent, Roberto is far below Malin on both the height charts and the hotness scale. They eventually divorced in 2013.
Jessica Simpson and Billy Corgan
Long before her marriage to Eric Johnson, Simpson was linked to Smashing Pumpkins front-man Billy Corgan. Whether Corgan and Simpson were just singing together or something more, you had to hand it to baldy Corgan for spending so much quality time with a gal who does laps around him looks-wise.
Kate Winslet and Sam Mendes
While Sam Mendes and Kate Winslet have matching Oscar statues (he won Best Director for “American Beauty” and she won Best Actress for “The Reader”) they definitely did NOT have matching good looks, with Kate coming in light years ahead of her ex-hubby on the hotness scale. They divorced in 2010.
Kate Moss and Jamie Hince
Kate Moss has a habit of dating not-hot musicians. Case in point: “The Kills” guitarist Jamie Hince.
Jennifer Lopez and Marc Anthony
Marc Anthony gives hope to all those ugly duckings who never quite turned into swans. He struck gold the first time around when he married a former Miss Universe, and then he scored Jennifer Lopez. Neither marriage lasted, but for a guy nicknamed “Skeletor” by the press, he did good.
Christina Aguilera and Jordan Bratman
Music marketing executive Jordan Bratman said he enjoyed “Naked Sundays” with his wife Christina Aguilera. Could their split suggest that she did not?
A-list beauties and Adam Duritz
Despite his very, uh, eccentric, appearance, Adam Duritz has dated an impressive list of celebrity stunners, including BFFs Jennifer Aniston and Courtney Cox, Emmy Rossum, Winona Ryder, Gwen Stefani, and many more! In his defense, he is an incredible musician, and he seems … cool, so maybe that’s all it takes.
Now this one is the biggest mystery of all. Marilyn Manson doesn’t only get hot girls, he gets GORGEOUS ones like Rose McGowan, Dita von Teese, and Evan Rachel Wood. They say some girls love bad boys, so we guess some love reaaally bad boys who wear female breast implants and creepy contact lenses.
Julia Roberts and Lyle Lovett
Lyle Lovett. Definitely talented, and definitely lacking in the looks department. Even still, he not only dated the gorgeous Julia Roberts, he got her to marry him! And with that, a nation had one question: Huh wha?
Kate Hudson and Chris Robinson
Everyone was perplexed when golden girl Kate Hudson married Black Crowes singer Chris Robinson. Once again, the rock star element seems to be strongly in play. Having legions of fans = sexy, no matter what you look like. Robinson went on to land another hot wife, ex-model Allison Bridges.