SJP is a global fashion icon, the woman who made Manolos a household name. Matthew Broderick is Ferris Bueller. While forever beloved for skipping school, he has a much more low-key, dad-next-door vibe compared to his wife’s high-fashion persona.
It's the ultimate 'cool girl meets comfortable guy' pairing, and it works. He's clearly got that quiet confidence that doesn't need to shout.
Selena Gomez is a pop superstar, a business mogul, and a beloved public figure. Benny Blanco is a record producer who looks like he’d be fun to get a pizza with. When their relationship went public, the internet collectively went, "Him?" But look at them. He makes her laugh, he cooks for her, and he publicly adores her.
Benny is living proof that being a genuinely good, fun person who treats a woman like gold is the ultimate trump card.
She’s the stunning Swedish-Canadian actress who has graced countless screens. He’s the charming British actor who, while handsome, seems to have hit the jackpot. What’s his secret?
Perhaps it's that irresistible British accent combined with a personality that keeps a bombshell like Malin laughing. Whatever it is, he's doing it right.
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.
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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, put up with his antics for more than a decade of marriage! The two tied the knot in 2010 and have three children together. But she finally wised up in 2024 and filed for divorce.
She is the embodiment of classic Hollywood glamour, a Welsh beauty with a voice like velvet. He is a Hollywood legend in his own right, but let’s be honest, their 25-year age gap raised a few eyebrows back in the day.
Yet, two kids and more than two decades later, they're still going strong. Michael Douglas must be armed with a legendary sense of humor and a charm so potent it should be classified as a weapon.
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.
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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.
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!
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.
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.
Emily Ratajkowski is, scientifically speaking, one of the most beautiful women on the planet. Her ex-husband, Sebastian Bear-McClard, is a film producer who looks like he could be your friend's slightly chaotic older brother.
Their pairing was a masterclass in not judging a book by its cover. Clearly, he had a charisma and confidence that went far beyond what a camera can capture.
Kirsten Dunst has been America's sweetheart, a teen queen, and an indie darling. Jesse Plemons, affectionately nicknamed "Meth Damon," has a more subtle, everyman appeal.
They fell in love playing a married couple on screen, which proves his charm is a slow burn. He’s the guy who wins you over with his talent and undeniable depth, not flashy looks. It's the kind of love story you root for.
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.
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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 he’ll probably always be best known for his comedies.
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.
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!
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.
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.
The avant-pop princess Charli XCX is all edgy, futuristic cool. Her fiancé, George Daniel of The 1975, has the artsy, slightly disheveled drummer thing down pat.
On paper, it’s an unexpected match. But his quiet, creative energy seems to be the perfect grounding force for her supernova presence. It's a testament to the fact that sometimes, the coolest people are the ones who don't try so hard.
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.
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.
Mark Davis, the owner of the Las Vegas Raiders, is a man who rocks a bowl cut last seen in The Monkees era, drives a ‘97 Dodge Caravan like it's a status symbol, and collects more bewildered stares than fanny packs. Standing next to him is his wife—elegant, poised, seemingly from a different dimension of glam—which creates a visual pairing that could be described as punk rock colliding with a royal wedding.
But here’s the twist: Mark’s appeal isn’t about looks or fashion; it’s his unapologetic authenticity and billionaire quirkiness. Their relationship proves you don’t need a polished exterior to find an extraordinary match—just confidence to own your look, a magnetic personality, and maybe an unshakeable belief that haircuts are optional.
