Celebrities Whose Wives Are Out of Their League

They might be good at making romance movies, but Hollywood is definitely not the place to find a real-life fairytale romance. It’s sometimes easier to measure celebrity relationships in terms of days and hours instead of weeks and months, much less years! And if a famous couple does happen to make it to the marriage stage of the relationship, no one ever expects “‘Til death do us part” to last all that long. 

However, there are times when love blossoms in Hollywood despite all the odds being stacked against true love. And while that might be rare enough, there are some celebrity marriages that are truly perplexing because one member of the happy couple definitely married out of their league! 

Today, we’re taking a look at some of the stars of Hollywood who managed to find wives that were completely out of their league. Whether it’s because they aren’t particularly famous or aren’t particularly stunning, these folks lucked out in the marriage department. Love isn’t all about looks…but it is a little about looks, and that’s why some of these relationships make no sense! We hope these stars realize just what a catch they’ve managed to score because marriages like these don’t come around very often! 

Let’s get started!

Fellow actors Dax Shepard and Kristen Bell have been married since 2013 and have two children together. At this point, it's clear the two make a very happy couple. But, from the outside looking in, we're not quite sure how Shepard has managed to make things work with Bell for so long.

Between Shepard’s sometimes annoying “goofy” persona and look to his much more serious struggles with addiction, it’s clear that this relationship is probably not a walk in the park for Bell. However, she’s managed to make it work somehow, and Shepard should probably thank his lucky stars for that! 

Throughout her career, Ellen Degeneres has broken barriers and challenged stereotypes. She proved that women can do anything and everything—including marrying out of their league! The talk show host and funny woman tied the knot with the gorgeous actress Portia de Rossi in 2008, four years after the couple started dating in 2004. 

De Rossi has had an impressive career of her own in Hollywood, with some of her biggest appearances including Arrested Development, Nip/Tuck, Scandal, and Ally McBeal. How and why she never tried her hand at modeling is beyond us! De Rossi is younger than DeGeneres by 15 years.

From his rapping days to his Law and Order: SVU days, everyone loves Ice-T for one thing or another, but let’s be honest—it’s not like modeling agencies are beating down his door trying to sign him up. He’s no Phantom of the Opera, but he’s no Fabio either! 

However, his wife, Coco Austin, definitely knows how to turn a few heads with her good looks. She got her start in the world of modeling at age 18, and she’s definitely not afraid to show a little skin in her numerous appearances in ads, on TV, and in movies. 

(Images via Mike Coppola/FilmMagic/Getty Images; Instagram)

On the one hand, it’s really no surprise that two of the most famous and powerful people in the world got together—Jay Z and Beyonce’s marriage was almost inevitable. However, on the other hand, there’s no denying that Beyonce’s looks have the ability to light up the room in a way that Jay-Z can’t. 

At this point, they’ve built a life together, so we can’t imagine Bey ditching her husband just for a new pretty face, but she’s definitely got that option, should the need ever arise! There’s probably a long line of absurdly handsome men who would be more than happy to take Jay-Z’s place! 

Hugh Hefner was truly a one of a kind celebrity. He’s the only person in history who took dating out of his league and turned it into a business model! There was rarely a time in Hefner’s life when he didn’t have a gorgeous young woman or two attached to his arm. 

From 2012 until his death in 2017, the gorgeous young woman attached to his arm was his third wife, Crystal Hefner. She made her debut on the Playboy website in 2008, and a year later, she had begun dating Hefner and appearing on the Playboy-themed reality show, The Girls Next Door. 

Sacha Baron Cohen has made a major name for himself in Hollywood. Unfortunately, he’s proven that he’s not afraid to act a complete fool in order to earn that name—and piss a bunch of people off in the process! From Borat to Bruno, this comedian has ruffled feathers and gotten laughs by any means necessary. 

So we’re not sure why his wife, the gorgeous Isla Fischer, has put up with his antics for more than a decade of marriage! The two tied the knot in 2010, and they currently have three children together. Let’s hope she keeps them from watching Dad’s movies and shows! 

The marriage between Good Charlotte guitarist Benji Madden and actress Cameron Diaz makes absolutely zero sense. Madden is by no means a bad-looking dude, but of all the men in the world, did you really expect Diaz to fall for the guy covered in tattoos and playing in an angsty rock band? 

We don’t have any idea how these two manage to make their relationship work because they are definitely one of the oddest odd couples we’ve ever seen in our lives! However, somehow they’ve managed to make magic, as they’ve been married since 2015, and they’ve even had a child together. 

(Images via Donato Sardella/Getty Images Entertainment/Getty Images; Mikel Roberts/Sygma/Getty Images)

We’re not sure why anyone would want to put up with Howard Stern. Between his crass and opinionated on-air persona and his ridiculous curly hairstyle, it’s a miracle that the man has managed to get a single date, much less get married! But that’s exactly what this radio shock jock has managed to do. 

Since 2008, Stern has been married to Beth Ostrosky, and, let’s just say that she more than makes up for what he lacks in the looks department. This blonde bombshell has appeared in movies and on TV and has even worked as a model for her own line of calendars. 

Geoffrey Arend has had an underwhelming career in Hollywood, to say the least. Aside from voicing a small part in the MTV animated series Daria, Arend’s biggest claim to fame was as a guy who ate an entire bag of psychedelic mushrooms in Super Troopers. Just real riveting stuff! 

However, lack of fame in Hollywood didn’t stop him from tying the knot with gorgeous actress Christina Hendricks in 2009. Hendricks, unlike her (now ex) husband, became massively famous thanks to her role on the TV show Mad Men. Unfortunately, Arend and Hendricks announced their divorce in 2019, but they did not announce a specific reason for the split.

Long marriages are something of a rarity in Hollywood, but Judd Apatow and his wife, actress Leslie Mann, have somehow managed to make their relationship work for more than two decades at this point. Apatow has made numerous acclaimed movies, but unfortunately for him, he’ll probably always be best known for The 40 Year Old Virgin.

Leslie Mann is beautiful and talented enough that she could have her pick of suitors, but she seems to have settled on Apatow. Love is a fickle, funny thing like that sometimes. Currently, the couple have two children together. 

David Cross made a name for himself as an opinionated comic who’s not afraid to say what he’s thinking and go in for the kill. It’s not exactly a personality type that the ladies seem to fawn over, but he’s done just fine in the relationship department, as he’s been married to Amber Tamblyn since 2012. 

Tamblyn, who is roughly two decades younger than Cross, got her big break with the title role on the TV show Joan of Arcadia. Since then, she’s appeared in films like 127 Hours and The Sisterhood of the Traveling Pants. In addition to acting, she’s published multiple books of poetry as well as a novel. 

From a fashion standpoint, Sean Penn has made some questionable decisions over the years. We’re still not entirely sure that he can pull off facial hair! However, any aesthetic deficiencies he may possess haven’t stopped him from having massive luck with the ladies, including his most recent ex-wife, Leila George.

George, who hails from Australia and works as an actress, was in her late 20s when she and Penn (who was in his late 50s at the time) tied the knot in 2020. Unfortunately, it doesn’t seem like things were meant to be with this couple, as they officially split in 2022. 

As great of an actor as he may be, even in his younger years Robert Duvall has never been much of a looker. He may have appeared in massively popular, classic movies like The Godfather and Apocalypse Now, but let’s be honest—there weren’t many teen girls with Robert Duvall posters on their walls. 

However, despite all this, Duvall has still been attached to several beautiful women over the years. He’s been married four times, and his current wife is the gorgeous Argentinian actress Luciana Pedraza. Despite being 51 herself, Pedraza is forty years younger than Duvall, who is currently 92. 

Despite Seth Green’s talent, there aren’t a ton of women in the market for a 5’4” comedian boyfriend. However, he’s still managed to nab himself a beautiful and talented wife who has no issue being the tallest one in the relationship. He’s been married to actress Clare Grant since they tied the knot in 2010. 

Grant is no stranger to show business herself, with appearances in projects like Walk the Line, CSI: Miami, and Star Wars: The Clone Wars. Additionally, she’s founded her own media company, Team Unicorn, that has become famous for the release of several parody songs. 

If you’re not familiar with Lyle Lovett, he’s basically what would happen if the guy from Eraserhead pursued a career in country music. And as strange as it may seem, Lovett had a highly publicized marriage to America’s Sweetheart herself, Julia Roberts, in the early ‘90s after meeting her on the set of The Player. 

Lovett and Roberts eloped less than a month after they began dating each other in May of 1993. However, this whirlwind romance wouldn’t last, as they divorced only a few years afterward in 1995. They said things didn’t work because of their career demands, but that was far from the only thing wrong with this strange relationship. 

(Images via KMazur/WireImage/Getty Images; Hulton Archive/Moviepix/Getty Images)