15 Ugly Celebs Who Still Manage To Date Hot Girls

Hollywood is known for encompassing some of the most beautiful people in the world. The women are seen as some of the most stunning females from all around the globe and even the men are groomed and manicured in every possible way. Yet, not every celebrity is known solely for their looks. In fact, there are quite a few celebrities that don’t exactly fit into the category of being described as a “beautiful person.” While beauty is in the eye of the beholder, it’s hard to deny that fame and fortune can be more of a draw than actual looks.

Some of the biggest examples of this have been evident in the marriages of some of the most high-powered executives in the entertainment industry. It’s not a coincidence that some of the richest and most powerful people in Hollywood get some of the hottest women in the industry. From Tommy Mottola marrying both Mariah Carey and Thalia to Salman Rushdie marrying Padma Lakshmi, it’s obvious that looks aren’t the only factor in choosing a mate. Yet, it’s not always money and prestige that can appeal to beautiful starlets since talent, personality and a sense of humor are also hugely important. Although there are a number of celebrity couples that look like the typical Barbie and Ken combination, there are also a few that look like a complete mismatch in regard to looks. Check out our list of the 15 ugly celebrities that still manage to get hot girls and see how not everyone needs to be George Clooney in order to land a beautiful “plus one.”


15 Howard Stern

There aren’t many people that hail from radio that have had the same kind of success like Howard Stern. He made a huge name for himself as a shock jock on the radio waves but many loved to watch his show because of the scantily clad women that were often guests. It seemed like Stern was constantly surrounded by big busted blondes and there was always someone throwing themselves at him. In 2008, Stern married the beautiful blonde, Beth Ostrosky, and he increased his popularity after becoming a judge on America’s Got Talent. Stern is no longer only thought as a radio personality, which is definitely a reason why he seems far more appealing to women. While he seems to have found the last woman in his life, there’s no question that he’d be able to get another beauty if this marriage were to fall apart.

14 Lil Wayne


While there are a number of rappers that have come out with a few hit singles and then never heard from again, Lil Wayne has been able to stay at the top of his game. Although he may have started out as the youngest member of Cash Money Records, he has since been able to move out from under that shadow and start his own enterprises. He has even gone on to help spawn the careers of some of the biggest artists in the music industry, including Nicki Minaj. While no one can deny that he is super talented and insightful as a music mogul, no one can truly think of him as swoon-worthy in regard to his looks. Every time he’s photographed, it looks like he’s just rolled out of bed and the whole teardrop tattoo look isn’t exactly the most appealing style.

13 Kevin James

Kevin James is an actor that has had an equal amount of success on both the small screen and in film. While some know him best for his role as Doug Heffernan in The King of Queens, others know him simply as “Mall Cop.” James has had consistent work over the years and landed a brand new show after The King of Queens ran from 1998 to 2007. Kevin Can Wait is being received extremely well and CBS went ahead and ordered 22 episodes of this new series in October of 2016. Yet, even with him obtaining consistent work, he isn’t exactly thought of as one of Hollywood’s most sought-after leading men. While he may not be thought of in the same light as Brad Pitt, that doesn’t mean he can’t ever get a beautiful woman on his arm. His wife, Steffiana de la Cruz, is a gorgeous addition to any red carpet event and Salma Hayek described her on The Wendy Williams Show as “stunning.”

12 Chris Rock


Chris Rock got his start in the entertainment industry as a stand-up comedian but quickly transitioned to the big screen and has acted in a number of memorable films. From the Beverly Hills Cop film series to New Jack City, Rock can legitimately call himself an actor. Yet, he’s not exactly one of the best looking actors in Hollywood. He is known more for his comedic ability rather than his appearance but that hasn’t hindered him in nabbing some truly beautiful women. Although his marriage to Malaak has come to an end, he seems to be keeping his bed warm without any problems. He has been most recently linked to the beautiful Megalyn Echikunwoke and has mentioned how much women have hit on him since his recent divorce.

11 Seth Green

Seth Green is thought of as a comedic actor and has been featured in a number of roles on both TV and the big screen. One of his most famous roles was in the Austin Powers film series but he’s also starred alongside some of the biggest names in Hollywood. On television, Green was actually part of a major storyline on HBO’s Entourage, playing a fictionalized version of himself. In the storyline, Green always had a large entourage with him and there were mentions of his prowess with women. He insinuated a sexual relationship with Eric’s girlfriend, which seems probable in real life as well. He’s been romantically linked to some of the most beautiful women in Hollywood and married the gorgeous Clare Grant in 2010.

10 Ed Sheeran


The world has always had a bit of leeway regarding the looks of rock stars since talent as a music artist can go a long way. While Mick Jagger may have the moves and the girls, he isn’t exactly thought of as one of the entertainment industry’s hottest men. So, when Ed Sheeran first came onto the music scene, there weren’t many people that were drooling over him in the same way they drool over Harry Styles. Yet, as his music evolved and his star began to rise, it seemed like he started to look more and more appealing. Nowadays, he has one of the hottest songs played on the radio and it isn’t a coincidence that “Shape of You” is about a woman in Sheeran’s bed. He may not be the best looking bloke in the world of music but his talent and rising fame sure do help in raising his hotness factor.

9 Jay Z

No one can deny how talented Jay Z is in the world of Hip Hop. Ever since his first album, Reasonable Doubt, was released in 1996, Jay Z has been thought of as a leader in his field. On top of being considered one of the best rappers of all time, Jay Z has made a name for himself as a businessman and entrepreneur. Yet, it’s not just his business endeavors that make him out to be thought of as super successful. On top of making money hand over fist in his business dealings, he also managed to marry the “hottest chick in the game.” Jay Z and Beyonce were married in 2008 and have built quite a little family together. While there was some speculation regarding the state of their marriage, they must have settled things since the release of her Lemonade album. The very next headline-making news was that Beyonce was pregnant with twins.


8 Johnny Depp


There was definitely a time in Johnny Depp’s life when he was thought of as one of the biggest heartthrobs in Hollywood. Girls taped his Bop posters on their walls and roles from 21 Jump Street and Cry-Baby created a “bad boy” persona that was super appealing. Depp had a tendency to go for the roles that were more eccentric than others but audiences loved that about him. From Edward Scissorhands to Charlie and the Chocolate Factory, it was easy to spot a Johnny Depp performance. While it was once thought of as an amazing acting choice, it’s starting to look like his onscreen characters are affecting his real life persona (and not in a good way). His recent appearances on the red carpet look way too close to his Jack Sparrow character from the Pirates of the Caribbean franchise and his erratic behavior seems to mirror it as well. Yet, that didn’t stop Amber Heard from marrying him in 2015. Although the two have since divorced, that doesn’t mean she will be the last beauty to walk with him on the red carpet. There’s no doubt that Depp will be able to find a new beauty, regardless of the rumors surrounding his personal life and his strange new look.

7 Steven Tyler

As the frontman for Aerosmith, Steven Tyler has made quite a name for himself as a rock star and all around legend in the music industry. During their heyday, they revolutionized the way music videos helped to tell a story and even helped spawn the acting career of Alicia Silverstone. Tyler was able to gain even more fame as a judge on American Idol but it may not have been that good of an idea to put him front and center with those glaring lights on the show. Not only did it highlight his eccentricities in clothing and overall look but it gave fans a super close look at his deep-set wrinkles and over-pronounced features. While he wasn’t looking like Tom Cruise at the Idol desk, he was still getting young girls giving googly eyes at him wherever he went. The most recent headlines involve him dating Aimee Ann Preston, who's 28 years old.

6 Rob Kardashian


When Rob Kardashian was first introduced to audiences through the reality series, Keeping Up with the Kardashians, he seemed like the annoying little brother that would have much rather be an only child. Early seasons of the series showed his sisters showing up on his dates to embarrass him and getting way too involved in his relationship with Adrienne Bailon. Although he was considered to be a good looking young man for awhile, things took a turn for the worse when he began gaining an extreme amount of weight. Nowadays, he seems to have lost all of his self-confidence and doesn’t even bother to dress appropriately when he leaves the house. From sweatpants to joggers to more sweatpants, there’s nothing more unattractive than a man that doesn’t take care of himself. Yet, that doesn’t seem to stop the girls from throwing themselves at him. He was romantically linked to the beautiful British hottie, Rita Ora, and is now with Blac Chyna.

5 Tyga

When Kylie Jenner first became romantically linked to the rapper, Tyga, people were up in arms about their age difference and the strange connection he already had to her family. She was allegedly only 17-years-old when they first started dating and he already had a child with Blac Chyna, who was friends with Kylie’s sisters. To make things even more complicated Blac Chyna began a relationship with Kylie’s half-brother, Rob. While you can argue that he was getting all of these hot women because he must be super talented and charismatic, there have been many that have accused him of being an opportunist. It’s hard to deny that the Kardashian link helped gain more notoriety towards his rapping skills. There’s no telling what these beautiful women saw in him but it definitely wasn’t solely for his looks.

4 Sean Penn


There once was a time when Sean Penn was thought of as one of the hottest actors in Hollywood, even though he was unfortunate enough to be famous during the style choices of the ‘80s. His look during Fast Times at Ridgemont High may not have been his most appealing times but he more than made up for it in his future roles and his rugged offscreen moments. Women absolutely fell in love with his bad boy persona and intense passion in everything he did. However, it’s been quite some time since he was considered a young and hot actor in Hollywood. Nowadays, it looks like age has definitely caught up to him and he is probably wishing he applied a few more layers of sunscreen during his younger years. From the deep set wrinkles to the crazed hairstyle, it’s surprising that he is still able to turn heads in Hollywood from young beauties.

3 John Krasinski

John Krasinski has had some success on the big screen but most people know him for his TV role on The Office. He was seen as a moderate actor until he became romantically linked to the Academy Award winning actress, Emily Blunt. There was a lot of talk while the two were dating because she seemed completely out of his league and not just because of her stellar talent as an actress. Krasinski appeared on several talk shows and referenced how intimidated he was when he first met Blunt and even mentioned the doubt he felt when he asked her to marry him. Yet, personality and a sense of humor definitely worked wonders with him because she said yes and the two have made a lovely little family together.

2 Mickey Rourke


There was a time when Mickey Rourke was thought of as one of Hollywood’s hottest “It” actors on the big screen. He was a huge film star in the ‘80s and starred alongside Kim Basinger in the smash hit, 9 ½ Weeks. Yet, the next few years showed him starting to age in a not so attractive way, which no doubt became a factor in why he started to dabble in plastic surgery. While it’s usually the women in Hollywood that destroy their faces through too much plastic surgery, Rourke proved that men can have the same tendencies if they aren’t being held back. Nowadays, Rourke looks like a photo for “what not to do” when dabbling in a few lunchtime procedures. Yet, that hasn’t hurt his chances with the ladies in the slightest. Since he still seems to get lucrative roles on the big screen, it’s probably the fame and fortune that has women throwing themselves at him.

1 Russell Brand

Russell Brand is a comedian and actor that has had quite a wide range when it comes to how he’s evolved over the years. While he was once only thought of similar to a slapstick comedian, he has since grown to be quite a philosopher in his ideas about the world and politics. When he married Katy Perry, people thought of them as a great couple due to their similar eccentricities. Yet, no one could deny that he seemed a little beneath her in regard to looks. Brand has a reputation of keeping a long and greasy hairstyle and doesn’t often smile due to his oversized gums and irregular facial expressions. The couple wound up divorcing in 2011 after only 14 months of marriage but that doesn’t mean he’s been having problems getting women. Brand’s new passion for trying to change the world for the better is undoubtedly a huge draw in helping to land him a new hot girl since he’s falling a bit short in the looks department.

Sources: E! News, US Magazine, Hello!

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