17 Male Celebrities Who Married Way Out of Their League

The men on this list are hardly monsters. They wouldn’t have become some of the most successful entertainers, athletes, and and businessmen in the world if they didn’t have the good looks to match their undeniable talent. It’s just that these male celebrities can’t help but pale in comparison to the otherworldly women they managed to marry.

 

 

We present this list not to poke fun at a bunch of famous “schlubs,” but instead, toast these gentlemen for their impressive achievements—and for giving us the hope that we, too, can convince an insanely beautiful babe to walk down the aisle with a modest-looking man.

1. Geoffrey Arend

 

 Christina Hendricks is best known for flaunting her unmatched, out-of-this-world curves as sexy secretary Joan on Mad Men. Her husband, Geoffrey Arend, is best known for swallowing a bag of weed in the cult classic Super Troopers. Dude: Tell us your secret.

 

 

2. Jason Dufner

Golfer Jason Dufner has a PGA championship under his belt, but his biggest trophy may be his beautiful wife, Amanda. The two met while Jason was playing for Auburn and Amanda attended archrival Alabama. She might just be his good luck charm: Shortly after getting hitched in 2012, Jason won his second PGA tournament in 3 weeks.

(If Amanda Dufner stepped on the green, she’d surely be one of The Hottest Women in Golf.)

 

3. Judd Apatow

You could say actress Leslie Mann owes her career to her husband, writer/director/producer Judd Apatow. He has cast her as the female lead in several of his box-office hits, including 1997’s The Cable Guy (where they first met on set) and most recently, 2012’s This Is 40. 

But we’d argue it’s the other way around: Mann often steals the show away from her big-time male costars—like Jim Carrey, Steve Carrell, and Paul Rudd—thanks to her killer comedic timing and serious sex appeal. Either way, props to Apatow for dipping his pen in the company ink, and giving us decades of screen time with our favorite Mann.

4. Howard Stern

The self-proclaimed “King of All Media” nabbed a worthy queen in 2008 when he married sexy actress Beth Ostrosky. The blonde bombshell is probably Stern’s favorite answer to his haters’ most common question: “How do you sleep at night?”

 

 

5. Jay-Z

With a reported net worth of $480 million, Jay-Z is the most powerful rapper in the universe. (He’s Not a Businessman—He’s a Business, Man.) Heck, he could buy a planet and it would barely register as a blip on his bank statement.

But beyond winning Grammys, starting record labels, and acquiring basketball teams, his single greatest feat is putting a ring on Beyonce—herself one of the wealthiest, most jaw-dropping women alive. Hova is a dapper dude, but no one’s in Queen Bey’s league. 

6. Andy Samberg

The Brooklyn Nine-Nine funnyman showed no shame in his days on SNL, donning hideous masks, wigs, and goatees to serve all jokes big and small. Ugly facial hair be damned, Samberg still married the stunning singer/songwriter Joanna Newsom in 2013.

Newsom hasn’t yet collaborated with Samberg’s faux hip-hop group The Lonely Island, but we can’t wait to hear how her delicate harp playing fits in with fare like “Dick in a Box.”

7. David Cross

How did the bald comedian—best known for his portrayal of Tobias Funke on Arrested Development—charm Amber Tamblyn, an actress 19 years his junior? One word: SkyMall. In 2008, the two met on a flight, where Cross cracked jokes about the now-defunct shopping catalogue in their seat-back pockets.

 

 

8. Sean Penn

In addition to an illustrious, varied silver-screen career, Penn boasts an equally impressive romantic record: When he married Madonna in the 1980s, she was the biggest female entertainer in the world, and he was still Spicoli.

Penn then moved on to the lovely Robin Wright, who now blesses our computer screens as First Lady Claire Underwood on Netflix’s House of Cards. Next up for the Oscar-winning actor: a rumored engagement to Charlize Theron. Tip of the cap to you, sir. 

9. Dax Shepard

The star of the recently wrapped Parenthood cut his teeth on the MTV prank show Punk’d—which is what we thought was happening to us when we heard that he tied the knot with Veronica Mars babe Kristen Bell in 2013. Shepard himself would probably agree that the Forgetting Sarah Marshall star is a bit out of his league, but he’s certainly seized his opportunity: Last year, Bell told us that Shepard was the perfect husband.

 

10. Robert Duvall

The 84-year-old legend is on his fourth marriage, but hey, practice makes perfect. His current wife, Luciana Pedraza, is an Argentine actress who also has her MBA. They met in Buenos Aires after she invited Duvall to a party without knowing who he was, started dating, and got hitched in 2005.

Fun fact: The couple share the same birthday—only 41 years apart. Well done, Bobby.

 

 

11. Seth Green

There are many things you might not know about actor Seth Green: He was one of the kids in Stephen King’s It; he’s the voice of Chris on Family Guy; he created the Adult Swim mainstay Robot Chicken; and his wife is ridiculously attractive. Green exchanged vows with actress Clare Grant in 2010. Good on the 5’4’’ Green for, uh, reaching for the stars. 

12. Lyle Lovett

After just a 3-week romance, country singer Lyle Lovett eloped with pretty woman Julia Roberts at the peak of her powers in 1993. The marriage lasted only 2 years, but you know what they say: It’s better to have loved and lost Julia Roberts than to have never loved Julia Roberts at all. 

13. Hugh Hefner

With a name synonymous with soft-core (but tasteful!) porn, we don’t question the 88-year old Playboy founder’s ability to pull in perfect 10s—just how he’s still doing it after all these years. Hef met model Crystal Harris at his mansion in 2008 and made her his wife 4 years later.

Never heard of Harris? Give her a quick Google search. Just not at work.

 

 

14. Russell Brand

Although they split in 2012, British comedian Russell Brand called America’s Sweetheart Katy Perry his wife for 2 remarkable years. Brand has a ton going for him—his sharp wit, his fearless opinions, his funny accent—but we still can’t quite figure out how he managed to nab the sexy pop star. 

 

15. Donald Trump

You can take or leave his politics (ditto his comb-over), but you can’t argue with the real-estate mogul’s impeccable taste in women: First there was Czech model Ivana Zelnickova, then came actress Marla Maples.

The Donald’s been with his third wife, Slovenian model Melania Knauss, for 10 years—but judging by his track record, it may not be long before she hears his famous words: “You’re fired.”

 

16. Gene Simmons

Simmons has aged about as well as you’d expect a 65-year-old rock star to. (It’s hard to tell if the KISS frontman looks better with or without the makeup. Kidding!) But his wife, former Playboy model Shannon Tweed, is still smokin’ at age 58. Luckily for Simmons, we know she’s in it for the long haul. Although the pair only got married in 2011, they were together for 28 years—with two kids, to boot—before tying the knot.

 

 

17. Dennis Kucinich

You might remember former Ohio Congressman Dennis Kucinich from his failed presidential run in 2008. He campaigned for universal health care, clean energy, and the legalization of marijuana. But enough about his policies—remember his insanely hot, way-too-young-for-him wife, Elizabeth? (He’s 68, she’s 37.)