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15 Losers Who Scored With The Hottest Women In Hollywood

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15 Losers Who Scored With The Hottest Women In Hollywood

An entire branch of science is devoted to the study of how animals, including humans, select mating partners. It’s called evolutionary biology. It deals with the evolutionary process that produced the diversity of life we see on Earth today. Ultimately, the reason you and I exist is because those before us made certain mating choices. Not to be crude, but what if your great-grandparents had chosen to do the nasty with different people? You wouldn’t be here today. The study of evolutionary biology is fascinating when you look at it that way.

Perhaps the most interesting idea put forth by evolutionary biologists is that of assortative mating. According to this theory, individuals with similar phenotypes, or characteristics, mate with each other more often than they would under a randomized mating pattern. In other words, animals mate with other animals that are like them. In the context of humans, assortative mating manifests in hot people scoring with other hot people and ugly people scoring with other ugly people. It’s how Tom Brady ended up with Gisele, while Tom Arnold had to settle for Roseanne.

Imagine how messed up it would be if human mating activity was completely random. Ugly dudes would totally love it. They’d have a much better chance of ending up with a hot chick than they do in an assortative mating dynamic. Jessica Biel, rather than ending up with coolest-man-alive, Justin Timberlake, might be knocking boots with your fat neighbor right now.

But somehow, someway, complete losers exist and they’ve even managed to bend the rules of science. They’ve hooked up with chicks whose phenotypes far surpass their own. No one is quite sure how they did it. But maybe evolutionary biologists can unlock the mystery one day and provide hope to losers and scrubs everywhere. Here are 15 total losers who have scored with the hottest women in Hollywood.

15. Pete Doherty

Take a look at this loser. Just look at his face, his body, and the way he’s dressed. That’s Pete Doherty. His Wikipedia page lists him as a “singer” and “poet.” But I’ve never heard any of his songs nor read his poetry. He also used to be a frontman for the rock groups The Libertines and Babyshambles. I must have missed all their chart-topping hits. I mean, let’s be real. If this dude walked into any college bar in America and tried to score with a solid ‘7’ from the local university, he’d get shot down, right? But check out his track record. He was scoring with Kate Moss, one of the hottest models of the ’90s for several years. Then he knocked up singer Lisa Moorish (she used to get it on with one of those Gallagher dudes from Oasis). He also had a baby with another supermodel, South African beauty Lindi Hingston. Darwin is scratching his head in his grave.

14. Rick Salomon

Rick Salomon is supposedly a film producer. At least that’s what he claims at Hollywood parties. But try to name a movie he’s made. The guy is really just known for scoring with a bunch of hot chicks. No one is quite sure how he does it. He was married to Shannen Doherty, better known as Brenda from 90210. Then, in perhaps his most famous liaison, he and Paris Hilton got down and dirty on tape. He was married to Pamela Anderson not once but twice, from 2007-08 and from 2014-15. All those chicks are clearly way out of his league. So how is he bending the rules of evolutionary biology to his will? The Hilton tape, though hard to discern in that awful green night-vision hue, reveals one potential clue for how he does it.

13. Kevin Federline

Did you really think I’d leave him off the list? Kevin Federline‘s marriage to Britney Spears might be the biggest head-scratcher of the 2000’s. Remember, the marriage happened before Britney’s head-shaving, crotch-flashing, total weirdo stage that caused her stock to plummet. She was still on top of her game. Hell, she wasn’t far removed from her relationship with one of the world’s most desirable men, Justin Timberlake. It was just baffling. Think about what it typically takes for a dude to score with hot chicks. Three traits immediately come to mind—good looks, talent, and money. Now think about how many of those three K-Fed had. To paraphrase Meat Loaf, zero out of three is, well, pretty bad. The guy singlehandedly set the career of the country’s hottest pop star on a precipitous downward trajectory that was nearly irreversible. It took her a full decade to return to some semblance of hotness and respectability.

12. Marilyn Manson

It might be unfair to call Marilyn Manson, real name Brian Warner, a loser. The dude had a bunch of hits in the mid-90’s, before Eminem supplanted him as middle America’s worst nightmare. He even got blamed for the Columbine massacre. I always found that amusing because Blink-182 had far more disturbing songs than Manson (look up the lyrics to “Degenerate” if you don’t believe me). For the record, none of the rumors that circulated about Manson were true. He doesn’t worship Satan, and he didn’t have three ribs removed so he could, well, you know. But you know what he did and still does? Score with hot chicks. He was married to burlesque dancer Dita Von Teese. She’s the hottie in the picture above. He also hooked up with Evan Rachel Wood. And back in the early 2000’s, he and Charmed actress Rose McGowan were engaged. No doubt Manson has talent. Hell, I won’t lie, I still rock out to “The Beautiful People.” But for any hot chick reading, have you ever, even once, looked at this guy and thought, Mmmm, I’d love to score with him?

11. Eric Benet

To be fair, Eric Benet isn’t a bad-looking guy. He probably isn’t poor and he’s achieved a measure of success in his career. He’s even been nominated for a few Grammys, albeit in categories I’ve never even heard of. But we’re talking about Halle Berry here. She could get 99.99 percent of dudes in the world. And back in the early 2000’s, when she was married to Benet, the number was more like 99.99999 percent. So it doesn’t quite make sense how she ended up with a “neo-soul singer/songwriter” on the fringes of stardom. What the hell is neo-soul anyway? Benet was Berry’s second marriage. Her first was to baseball player David Justice. Now that guy was a stud—good-looking and athletic. It’s always puzzling when chicks make a huge step down in their mating succession. We saw it earlier with Britney, and now Halle. Evolutionary biology is an enigma wrapped in a mystery.

10. Jermaine Dupri

Jermaine Dupri has worked with a host of talented musicians on hip hop projects. In his decades-long career, he’s collaborated with Usher, Jay-Z, Nelly, Ludacris, Mariah Carey, and more. But he always seems to be the guy behind the scenes and never the headliner. That’s probably because he’s five-foot-four and not good-looking at all. He’s not exactly an image guy or the dude you want as the face of your brand. But even being tangentially involved in the rap game seems to translate to endless scoring opportunities with hot chicks. Dupri was involved with Janet Jackson for eight years. I’m no scientist, but I think the above picture of Jackson and Dupri side by side might disprove the theory of assortative mating. Apparently, after eight years, she got tired of waiting for him to pop the question and ended the relationship. Dupri now admits that he “messed up” with Janet.

9. Hugh Hefner

Hugh Hefner has a net worth of $43 million. So I guess no one should be too surprised that he still pulls hot chicks at 91 years old. But then again…91 years old?!? Something to aspire for, right? He’s had three marriages; the most recent one in 2012, and none of his wives were older than 26 at the time of the wedding. His current wife, Playboy model Crystal Harris Hefner, is 60 years younger than him. That’s a massive age gap that looks even bigger when you retroactively apply it. When she was in preschool, Hef was eligible for Medicare and Social Security. She looks pretty happy in all their pictures together, though. That’s probably because she’s studied the actuarial tables and knows that $43 million should be hers sooner rather than later. But in the meantime, Hef’s proving that you’re never too old to work it. Viva Viagra!

8. Antwaun Cook

Fantasia has a unique look, and not everyone thinks she’s fine. To be honest, she’s not really my gig, but I can see how dudes with different tastes might go for her. She’s talented to boot, having won American Idol back in 2004. So even if she’s not on the same echelon as Zac Efron or Ryan Gosling in the assortative mating hierarchy, she should have no dearth of high-quality male suitors. So, how did she end up with Antwaun Cook, some scrub known for nothing apart from knocking up a famous singer (that singer being Fantasia, back in 2011)? Moreover, Cook might have still have been married when she pursued him. In a divorce proceeding, his ex-wife claimed Fantasia made a pass at her husband before they were legally separated. Fantasia denied it, and the court ruled in her favor. Three years later, in 2014, Fantasia admitted she was still bitter over Cook leaving her.

7. Marc Anthony

How did a dude who looks like the Latin Skeleton end up with arguably the most bootylicious chick in Hollywood? It couldn’t have been his money. Marc Anthony‘s well-off, but she has oodles more dough than he ever did or will. His talents? I guess he’s a good singer and dancer. But J-Lo‘s been with dudes like Ben Affleck who were talented and actually pleasant to look at. Is he packing? Hmmm…now we might be on to something. Allegedly, an unnamed groupie told a celebrity gossip rag back in 2011 that Anthony is “so well-endowed it’s scary.” So that might explain part of the attraction. But I’m still not convinced. J-Lo is so hot she could find tons of guys who are rich, talented, good-looking, and who have the whole “package.” My theory, based on her voluminous dating history, is that the chick doesn’t know how to be alone. So when one relationship ends, she jumps right into another without assessing quality first.

6. Russell Simmons

Take a long look at the picture above. How in the world does that happen? Pretend you don’t know who the dude is and you happen to see this couple at the beach. The dude is clearly pushing 60. He’s not remotely good-looking, and he’s sporting a physique that could charitably be described as a “dad bod.” The chick, by contrast, appears no older than 30, has a flawless physique, and looks as though she’d turn any male head on the beach. So can you think of any good reason these two are together? I can give you 500 million of them. That’s the net worth of the dude in the picture, Russell Simmons, the guy who founded Def Jam Records. He was married for most of his career but got divorced in the mid-2000’s. Since then, he’s been Donald Trumping it—using his vast riches to score with chicks he otherwise has no business scoring with.

5. Cash Warren

Jessica Alba was the hottest chick on the planet in 2007. Literally every dude wanted to get with her. She was the chick you always used in conversation to provide a frame of reference when talking about hot girls. Like, “How hot was that chick you met last night? Was she Jessica Alba hot?” Then, seemingly out of nowhere, she turned up pregnant, and not a single person had ever heard of the baby daddy. It turned out to be some dude named Cash Warren. He has an IMDb profile. But it’s pretty bereft. He’s been in a few movies, though I can guarantee you’ve never heard any of them. And you can look the above pic and judge for yourself, but I think it’s safe to say his good looks aren’t what attracted Jessica. Yet here it is. A decade later, he’s still married to Jessica Alba, while we’re over here reading/writing snarky articles about how unfair it is. Is he really the loser here?

4. Jesse James

Before his headline-grabbing marriage and divorce to Sandra Bullock, Jesse James was only quasi-famous. He was an outlaw biker dude with a reality show about fixing motorcycles. He wasn’t an A-list celebrity, nor was he particularly good-looking. Then he snagged Sandra, a definite A-lister with a penchant for dating down (right now she’s involved with a freelance photographer from L.A. who smokes indoors and appears to shop only at Walmart). Suddenly, everyone knew who Jesse James was. But once people took a good look at him, no one quite understood why, with Sandra’s seemingly endless options, she’d choose him. It turned out to be an awful choice, to say the least. Jesse was what you might describe as a low-rent Tiger Woods. He chased anything in a skirt, and I guess chicks wanted to be able to say they scored with Sandra Bullock’s man, because the slimeball actually succeeded. Sandra finally came to her senses and divorced him. But given her current relationship, she still hasn’t figured out this whole assortative mating thing.

3. Dax Shepard

A Rubik’s Cube is less confusing than the picture above. I honestly believe Kristen Bell is one of the three or four hottest women in Hollywood right now. She’s got the body, the smile, the personality, and the “it” factor. She just oozes with sexiness. And then there’s her husband, Dax Shepard. The picture above says a thousand words, but I’ll add a few more. First, the obvious—he isn’t good-looking. Second, this isn’t a Jay-Z and Beyonce situation where the ugly dude has once-in-a-generation talent to make up for his lack of looks. Shepard’s creds include a stint on Punk’d and a supporting role on the TV show Parenthood. He was in the movie Idiocracy, which was pretty good but not because of him. In short, it just makes no sense that he’s scoring with (and married to) Kristen Bell. He must’ve won her over with all that social awareness jive. He famously stated he wouldn’t get married until same-s*x marriage was legal everywhere. Minutes after the Supreme Court handed down its decision in Obergefell vs. Hodges, he Tweeted his proposal to Bell. What a romantic move!

2. Dean McDermott

Take a gander at that goofy-looking SOB above. That’s Dean McDermott. He’s been married to Tori Spelling since 2006. Before that, his wife was Mary Jo Eustache, host of the Canadian cooking show What’s for Dinner? Dean’s never had a career, so he doesn’t have talent or money to make up for his homely looks. He scored with Spelling the first night they met, despite still being married to Eustache. In 2013, he went to s*x rehab (code for “I got caught cheating but if I use words like ‘addiction’ and ‘rehab’ people will perceive me as a victim and I’ll get sympathy”) after getting busted having at least five affairs. Poor Tori finally came to her senses and wants to divorce this loser, but can’t because she’ll owe him too much in alimony and will be financially ruined. It’s funny because people always call me sexist when I say alimony is a crock of s***. Yet here’s a woman getting screwed by it and (gasp) I still think it’s unfair.

1. Geoffrey Arend (Stoner From Super Troopers)

Remember the beginning of Super Troopers? Maybe the best opening scene in cinema history. You know, where the troopers pull over those stoners and mess with them? And remember the dork in the back seat who eats all the pot and ‘shrooms and then holds up the two empty bags and says, “Call Guinness!”? Did you ever watch that movie, maybe back in college, possibly while stoned yourself, and when that scene came on, say to your buddies, “I bet that dude scores with some major hot chicks in real life”? Me neither. It looks like we were both wrong, though. The dude’s name is Geoffrey Arend. His acting career pretty much started and ended with Super Troopers, though he’s had parts in a handful of other movies that appear to have either gone straight to DVD or gotten discarded on the cutting room floor. But apparently, Mad Max hottie Christina Hendricks watched his famous scene and liked what she saw. Despite being about a billion times better looking than him, she’s the one who pursued him the night they met, and on their very first date said she wanted to start a family with him! Okay, that’s enough! I might need to have plastic surgery.

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