TheRichest.com

15 Not So Attractive Celebs With The Best Luck With Women

When one half of a celeb couple is significantly more attractive than the other, it's hard not to wonder why.

When we're walking down the street and a stunning woman walks by hand-in-hand with some short, not so attractive bald guy, we immediately wonder, why that man is with that woman? As hard as we try not to be shallow, when one half of a couple is significantly more attractive than the other, our socially-conventional minds instinctually wander. If we're being honest with ourselves, let's admit that we usually assume the unattractive half of said couple is either rich, famous, or powerful.

Well, how do we explain the list of celebs that are consistently less attractive than their significant others if the people they date are also rich and famous? How did Jay Z convince the queen of America (Beyonce) to marry him? What's the voluptuous Christina Hendricks doing with that guy we see in movies but never remember (Geoffrey Arend)? The answer is both complicated and simple... these people have game.

There's something poetic about the fact that some of the same celebrities making a living off their looks, their hotness, and their public image do not look for the same superficial traits in their significant other. There's also something tragic about the fact that some people are just that much better at the game than the rest of us. At the end of the day, it's comforting to know that when it comes to our most beloved celebs, we might have a chance. For full disclosure, the attractiveness discrepancies mentioned in this article will range from moderate, like Clive Owen with Sarah Jane Fenton, to extreme, like Roberto Zincone with Malin Akerman.

15 Mac Miller Slid Into Ariana Grande's DMs

via YouTube

Mac Miller looks like he's Sam Smith's shorter, loser fraternal twin, but looks didn't stop this Pittsburgh rapper from meeting his soulmate. She just happens to be one of the most successful and lusted-after stars on the planet, Ariana Grande. Miller is a reputable hip-hop artist and released one of today's most streamed mix tapes, Best Day Ever, so it's not particularly strange that he could meet Grande on some occasion, but he got the Disney star to fall in love with him?! How?

Miller's dating history is relatively modest for a hip-hop artist, but dating even one worldwide superstar even close to Grande's level means he must know something the rest of us do not. What worked for Miller was sliding into Grande's DM's and proposing that they do a song together. Grande and Miller recorded several songs and still regularly perform together; they look nothing short of genuinely in love. Truth be told, they seem like one of the happiest celeb couples. It goes to show that one should never underestimate their reach on Instagram.

14 Evan Spiegel Turned Tech Into Dates

via Business Insider Nordic

Miranda Kerr grew up in Sydney, Australia, riding horses and racing motorbikes, which seems odd because we all presumed she was raised by mermaids or angels or some other kind of mythological being that births remarkably gorgeous people. Regardless of her upbringing, Kerr's beauty is renowned: Kerr is a Forbes top ten model, became the first Australian model to earn a contract with Victoria's Secret (which is shocking when we consider the seemingly endless pool of hot Aussies), and founded her own skincare company, KORA Organics. Due to her beauty and success, we need more information as to why Kerr married Snapchat CEO and Where's Waldo doppelgänger, Evan Spiegel.

Spiegel is worth a lot of money, but so is Kerr; it only starts to make sense if you look at Spiegel's controversial history with women. Before Kerr, Spiegel had a reputation for getting women to pose in revealing outfits on his app, had to publicly apologize for his behavior during his days at Stanford, and was at one time linked with super-dater, Taylor Swift. It's hard to pinpoint Spiegel's source for his game, but we know he embraces his sensitive side – he's particularly fond of flower arranging.

13 The Many Wives Of Billy Bob Thornton

via Huffington Post

Billy Bob Thornton does well for himself. He won an Academy Award for Sling Blade, currently stars in Amazon's Goliath (secretly the best lawyer show on TV) and he dated a distinguished list of beautiful actresses before he married a successful puppeteer named Connie Angland. When Billy Bob was married to everyone's favorite PTA member, Angelina Jolie, it's hard to forget the weird things they had going on. Instead, we should remember that Billy Bob broke off an engagement with Laura Dern so that he could date Angelina.  Honestly, Jolie's game trumps them all (as we recall, she pulled a similar move on Brad Pitt), but Thornton still had quite the rep. A look at Bad Santa's dating history shows that this soul-patching eccentric has a daughter with model Pietra Cherniak and married nineties babe Cynda Williams. Whether you think Billy Bob is attractive or not, we all agree his game is strong because he's convinced six women to marry him while simultaneously being a real-life crazy person.

12 Jason Statham Is Not Nearly As Good-Looking As Rosie Huntington-Whiteley

via: vogue.com

Jason Statham will never be in the same category of fame as our other elite bald actors (Bruce Willis, The Rock, Samuel L. Jackson, etc), but the transporter undoubtedly succeeds with beautiful women. Statham deserves credit for being in great shape (he was a world championship high diver) and he seems pretty tough (he does most of his own stunts), but this angry-faced hooligan still needed game to convince Rosie Huntington-Whiteley to marry him.

Huntington-Whitely is an English Victoria's Secret Angel and Megan Fox's replacement in the Transformers franchise. Nothing against Statham, but Huntington-Whiteley is a 10, and standing next to Jason bumps her to a 12. Before meeting his wife, Statham dated FHM's 2005 "S*xiest Woman in the World" Kelly Brook, and Australian pop singer, Sophie Monk. I mean, you must have noteworthy game if everyone you date is better looking and more famous than you, right?

11 Michael Sheen Landed Kate Beckinsale On Set

via Vanity Fair

Michael Sheen just concluded his role as Dr. William Masters opposite Lizzy Caplan on Masters of S*x, and he'll be back on the big screen in at least two horror films this year. Sheen began his career on stage before making it to Hollywood and landing roles in Underworld and Laws of Attraction. The ordinary-looking and seemingly plain Sheen must be able to lay on some powerful English charm because he's linked to several beautiful actresses.

Since 2014, Sheen's been dating the ageless comedian, Sarah Silverman. Before Silverman, Sheen dated Notebook star, Rachel McAdams, who is almost ten years younger and significantly more famous. Shockingly, the most attractive of Sheens' exes is his first famous girlfriend and baby mama, Kate Beckinsale. The two met on the set of Underworld and still maintain a very close relationship, which isn't just for the sake of their daughter, Lily. In fact, Sheen, Beckinsale, Silverman, and Lily have an enviable modern family dynamic which includes them online trolling each other. Instead of Sarah being jealous of Kate, it may be the case that Michael is the one jealous of the bond between his current and ex-girlfriend.

10 Miles Teller Claims His Confidence Got Him Keleigh Sperry

via Travel + Leisure

Miles Teller turned a lot of heads at the 2015 Academy Awards when we saw his now fiancée, Keleigh Sperry. Sperry stole the show during Teller's red carpet interviews, which called attention to the War Dogs actor's own lack of handsomeness. Teller's attractiveness was questioned so frequently that he once responded saying, "I probably think I'm better looking than the public thinks I am." During this dinner interview, Teller goes on to say that he's always done well for himself when it comes to the ladies. So how does the actor pull it off? Looking at Teller's history, it comes down to confidence, an important trait for a dramatic actor. In films, Teller doesn't give-up screen dominance to more attractive co-stars like Taylor Kitsch in Only the Brave, he seems to always play a guy with a hot girlfriend like in Divergent, and was the coolest kid in town in Project X. It's easy to appreciate Teller's smooth-talking in his movies, but his game is most solidified by the fact that Keleigh Sperry (a model that uses her body for work) has the initials" M.T." tattooed onto her body.

9 Adrien Brody Charms His Way Into Women's Hearts

via Zimbio

There is an indubitable lovability to Adrien Brody, a kind of aura that follows him on screen and off. Brody has that certain charisma which makes you forget what he looks like. Although he failed to revive the classic film favorites King Kong and Predators, Brody has a successful indie film career working with Wes Anderson and won an Oscar for The Pianist – his Academy Award acceptance became one of the most memorable when he kissed Halle Berry on stage. Remarkably, Brody should be just as proud of his relationships as his films. For brief periods before dating his current model girlfriend, Lara Lieto, Brody dated Monet Mazur, January Jones, and was engaged to Elsa Pataky (the Spanish actress and wife of Chris Hemsworth). We'll accept arguments for Brody being a decent-looking guy, but there is no way he's as attractive as Pataky or Hemsworth – their family looks like the stock photos for picture frames.

8 Jason Sudeikis Scored Olivia Wilde With A Great Pick-Up Line

via Our Campus Market

Jason Sudeikis currently enjoys a steady, bankable career: he co-starred with Jennifer Aniston in We're the Millers, plays a recurring character on The Last Man On Earth, and even flaunted some dramatic acting chops in Race. Sudeikis' career began on Saturday Night Live and, although he wasn't a dominant cast member, the comedian had a certain "every guy" likeness to him. In 2013, Sudeikis proposed to his longtime girlfriend, Olivia Wilde, a woman in decent contention for fairest of them all. It's not that Sudeikis got one of the most beautiful women alive, it's how he got her.

While on The Howard Stern Show, Wilde recounted an SNL after-party where Jason walked up to her at the bar and said, "You know, whatever you're looking for, you don't need it" and then he walked away, just like that. It's great news that the rest of us now know what to say next time we try to pick up an A-list movie actress sitting alone at a bar. Getting Olivia's number was no one-time fluke for Sudeikis; he's also been linked to January Jones. Jones most notably played Mrs. Betty Draper on Mad Men and was previously an Abercrombie & Fitch model. Considering Sudeikis' recent film disasters, (Father FiguresAngry Birds, and Downsizing), it's a good thing he has Olivia Wilde to come home to.

7 Elon Musk's Only Weakness Is Beautiful Women

via People

Elon Musk's name is most synonymous with Tesla and SpaceX, but if you ignored the fact that he's a world-renowned entrepreneur, an environmental hero, and one of the richest people alive, then Musk becomes an ordinary guy that just happens to be very positive about humanity's future. Musk is one of the most important and respected people alive and his fortune doesn't even begin to account for what he's done to change the world for the better. With that said, Musk also dates really pretty women.

Most recently, Musk broke up with Amber Heard, the beautiful Justice League actress who previously dated Johnny Depp. Before that, Elon was married to Westworld actress, Talulah Riley, who somehow looks like a hotter version of Uma Thurman. Musk must have worked on his game from an early age, because his ex-wife and college sweetheart, Justine Wilson, is also a babe. Wilson said Elon swooned her with invites to get ice cream, constantly sent her roses after he transferred schools, and once gave her a credit card to buy whatever books she needed. Elon Musk doesn't just know how to treat our planet, he knows how to treat our planet's women.

6 Ellen DeGeneres Has A Thing For Attractive Blondes

via Pinterest

Ellen DeGeneres is an easy top pick for people we'd like to invite to a dinner party, but the energetic daytime talk show host isn't exactly the modern-day Aphrodite. DeGeneres began her career as a stand-up comedian and eventually landed her own series, Ellen. More than just a hit sitcom, Ellen broke grounds when DeGeneres came-out publicly (both as her character and real-life self) during a fourth season episode. Ellen's coming out served as inspiration for several later series with openly gay characters like Will and Grace and Modern Family, which continue to challenge LGBT stigmas.

DeGeneres married Portia De Rossi, who's best known as Lindsay Bluth Funke on Arrested Development. Portia is gorgeous, but when she met Ellen, she was overweight and still in the closet. Regardless of how Rossi fell in love with DeGeneres, Ellen has some legitimate game. Before she was with Rossi, DeGeneres was famously with Anne Heche for three years – note that this was during the height of Heche's career, a time when Heche could date anybody.

5 There's No Debating Bill Maher's Game

via: thefrisky.com

From the moment we were introduced to comedian Bill Maher, he was surrounded by controversy. Maher became deeply entwined in the media's political world during the early nineties with his ABC series, Politically Correct, which became the prototype for his HBO series, Real Time. Fun fact: Politically Correct was suspended and then cancelled despite earning ratings comparable to Jay Leno's as a result of Maher making politically incorrect comments about George W. Bush and 9/11. Maher's career is contingent upon making enemies out of right-wing conservatives and religious leaders, but the sarcastic host is also known for repeatedly flaunting eye-candy on red carpets. The Cornell grad is smart, successful, and famous; however, that doesn't change the fact that he is not the most attractive man in Hollywood. Maher's never been married and is currently dating famous Canadian singer, Anjulie, who's a whopping twenty-five years younger than he is. For Maher, age and looks never got in his way. He's dated several much younger women including actress, Thora Birch and television host, Cara Santa Maria.

4 Kanye West Joined The Kardashian Family

via: pinterest.com

The world is quickly running out of topics that do not include the Kardashians. We're past the point of disputing the influence and worth of the Kardashians. We have no choice but to love them now. So, since we can't beat 'em, Kanye West joined 'em.

At the top of their family ranking is Kim Kardashian. She's beautiful, controversial, and truly one of history's most successful online marketers. Kim's husband, Kanye, is a self-proclaimed "genius" and has one of the more mysterious public personas. We could pick on Kanye for being arrogant all day, but he's still a rare talent who scores way hotter women than us. Before his breakthrough album, The College Dropout, Kanye was engaged to a good-looking fashion designer named Alex Phifer. More notably, Kanye dated Amber Rose, which caused many squabbles but still earns him credit, since dating him is what jump-started Rose's road to fame.

3 Howard Stern Is Famous For Getting Women Out Of His League

via: dawgshed.com

Howard Stern will be the first to tell you he's unattractive; he'll jokingly say it's why he chose a career in radio. It's hard to quantify Stern's power and influence on modern pop culture, but it's likely limitless. By the mid-nineties, Stern earned the title "King of All Media" for the massive fan base he earned with controversial on-air material (he's been sued by the FCC for over $2.5 million), absurd guest callers known as the Wack Pack, two books, and even a run for Governor of New York.

Despite looking like a thin version of Slash, Stern has rock star status and few celebs could turn heads like him when he walks into the room, even when he wasn't surrounded by a troop of scantily clad women. Although Stern claims that he's ugly, it didn't stop him from marrying model, Beth Ostrosky, who is almost twenty years younger than Stern. Ostrosky isn't the first model Stern dated: the media mogul was also linked to Sports Illustrated model Angie Everhart and Riverdale actress Robin Givens. Aside from his exes, there are dozens of models, adult film stars, and actresses that admit to crushing on Howard. So, whether he knows it or not, there is more to Stern's game than he admits.

2 Mark Webber Married Teresa Palmer

via Daily Mail

Mark Webber has what many believe to be the ideal acting career, one where you're working consistently in small roles so that most people don't recognize you on the street. Worldwide fame isn't everyone's goal; and, if we're judging by looks, Webber won't be replacing Dwayne "The Rock" Johnson in any San Andreas sequels. Webber is undoubtedly talented with great range. He played in everything from the Nickelodeon movie, Snow Day to the ultra-violent Jeremy Saulnier film, Green Room.

Webber's leprechaunish looks and low-tier status means he must have serious game, because the actor dated certified stunners. Webber is married to Teresa Palmer and they just had their second kid together. Teresa Palmer is basically Kristen Stewart with a personality; she's best recognized in Warm Bodies and Lights Out. Before the couple dated, Webber was with Blue Mountain State star, Frankie Shaw (they also have a kid together).

1 Giovanni Ribisi Dates Models And Pop Stars

via 7wallpapers.net

Giovanni Ribisi is an entertainment child: his father is a musician, his mother is a talent manager, and his twin sister, Marissa, is also a working actress (she played the redhead in Dazed and Confused and married the musician, Beck). Ribisi, along with his sister and brother-in-law, is a devout Scientologist. Ribisi's career is nothing short of character-acting perfection.

Ribisi consistently worked in both hit television shows like My Name is Earl and blockbuster movies like Saving Private Ryan. Among his roughly 100 acting roles, Ribisi never played the handsome hero. In fact, he usually plays the exact opposite: a creep weirdo, etc. Despite his eerie persona, Ribisi dated the crazy cute singer, Cat Power, and had the audacity to leave her so he could marry Agyness Deyn, a successful model from England. Karma came for Ribisi in the form of a costly divorce, but both Deyn and Power were reportedly heartbroken.

Give TheRichest a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheRichest?

Get Your Free Access Now!

More in Entertainment

15 Not So Attractive Celebs With The Best Luck With Women