15 Comedians Who Dated WAY Out Of Their League

For centuries, scientists, experts, and government officials have been conducting research to answer one of the world's most mysterious questions—how did that average-looking guy land that hottie with a body? Some assumed that the average man was rich or possibly an animal in the bedroom. The answer isn’t money, muscles, or performance but actually a sense of humor. Some gorgeous women just can’t resist a funny guy.

Fans, the media, and the general public can’t get enough of celebrity couples. Celebrity couples are often the center of attention and are under the harsh spotlight. Even with celebrity couples, many will point out that one is way out of the other’s league. Several of the funniest and most hilarious comedians date some of the hottest women in the universe. For many of these comedians, these women are out of their league. They might be rich and famous, but it still doesn’t explain how these goofballs landed the most beautiful women alive. There are many famous comedians that are simply hilarious but might be average in the looks department. There is certainly nothing wrong with that but they’re able to use their sense of humor to date women so beautiful even Dwayne Johnson or Jon Hamm would be nervous to talk to. For some women, it’s not just about the superficial or money. They look for something deeper and more meaningful. Plus, they don’t mind being made fun of on a regular basis. Here is a look at 15 Comedians Who Dated Way Out Of Their League.

15 Andy Dick Dated Jennifer Gimenez


Comedian and actor Andy Dick is one of the most controversial and polarizing celebrities. He’s known for his outrageous and outlandish behavior. However, he is also known for dating way out of his league. In fact, he’s dated some of the hottest women alive. He might not be the best-looking dude but he can make up for it in other ways. Andy Dick is best known for his appearances in several popular TV series, such as The Ben Stiller Show, NewsRadio, and Comedy Central Roasts. He was a contestant on the reality series Dancing with the Stars where he finished 7th.

From 1986-1990, Andy was married to the beautiful Ivone Kowalczyk. He has gone on to date some incredibly hot women. He had dated Playboy models Brande Roderick and Trishelle Cannatella. He seems to like models as he’s dated Inger Ebeltoft and Amber Smith as well as Survivor contestant Jessica Kiper. Most recently, he was linked to the utterly beautiful and simply hot Jennifer Gimenez.

14 Jason Sudeikis Engaged To Olivia Wilde


Comedian, actor and writer Jason Sudeikis is certainly a good-looking guy. He probably could date any woman he wants in his league. However, he decided to go way outside of his league to land one of the most desired celebs in Hollywood. Jason Sudeikis is best known for his time on Saturday Night Live. He recently provided the voice of Zorn in the live action/animated sitcom Son of Zorn. Additionally, he’s starred in the films Horrible Bosses, Hall Pass, and We’re The Millers.

In 2011, Jason Sudeikis started to date the ridiculously hot Olivia Wilde. Olivia Wilde has appeared in several memorable films, including Alpha Dog, Tron: Legacy, and Her. She also had appeared in the critically acclaimed series, House. Jason and Olivia met on the set of Saturday Night Live. They had both just went through divorces before meeting each other. They became engaged in 2013 and later had two children together.

13 Bill Maher Dated Karrine Steffans


Bill Maher is sarcastic, controversial, and funny—the quality traits that some women just can’t resist. Bill Maher has never been confused with Ryan Reynolds but that hasn’t stopped him from dating women way out of his league. Comedian Bill Maher is best known for hosting the late night political talk show Real Time With Bill Maher.

In 2005, Bill Maher dated best-selling author Karrine Steffans. She was a former hip hop model and video vixen. He previously dated Playboy Cyber Girl Coco Johnsen. In 2011, he dated neuroscientist and co-host of Skeptics’ Guide to the Universe, Cara Santa Maria. In 2014, he dated singer Anjulie Persaud. Despite dating exclusively hot women, he has no plans to get married. He once said, "I'm the last of my guy friends to have never gotten married, and their wives—they don't want them playing with me. I'm like the escaped slave—I bring news of freedom.”

12 Seth Green Married To Clare Grant


When one thinks of the hottest man on earth, Seth Green usually doesn’t come to mind. However, with his charm, personality, and sense of humor, he's able to date any hottie he desires. Despite having the body of a 12-year-old boy, he is married to one of the hottest women alive. Seth Green is best known for voicing Chris Griffin on the animated sitcom, Family Guy. He also created the popular series Robot Chicken for Adult Swim. Additionally, he has appeared in the films Austin Powers, Stephen King’s It, and the TV series Buffy The Vampire Slayer.

Seth Green is married to the utterly beautiful Clare Grant who has also appeared in a number of films herself, including Walk The Line, Black Snake Moan, and The Insomniac. She co-founded Team Unicorn, which specializes in music video parodies and web series. In 2009, Seth and Clare started dating and got married after just a year.

11 Seth Rogen Married To Lauren Miller


Seth Rogen does well for himself in the looks department. However, he’s not the typical hottie. He has the classic dad bod and is a major stoner. However, those minor details would never stop Seth from landing the hottest wife. Lauren Miller co-wrote and starred in the film For A Good Time Call. In 2010, after dating for several years, Seth and Lauren tied the knot. Lauren Miller has appeared in several films along with Seth in minor roles, including Superbad, Zack and Miri Make a Porno, and 50/50. Lauren Miller is clearly out of Seth’s league but she’s pretty lucky too.

10 Jim Carrey Dated Jenny McCarthy


It appears that some beautiful blondes find hilarious men to be simply irresistible. It helps that the funny man is world famous Jim Carrey. Jim Carrey has starred in several universally praised comedies, such as Ace Ventura: Pet Detective, The Mask, and Dumb and Dumber. Later, he moved into dramatic films and starred in Man on the Moon and Eternal Sunshine of the Spotless Mind.

In the '90s, it was probably difficult to find anyone funnier than Carrey. However, he has never been confused with a Calvin Klein model. That has never stopped him from dating the most gorgeous women in the world. In 2005, Jim Carrey dated the sizzling hot Jenny McCarthy, a former Playboy Playmate of the Year. They dated for 5 years before breaking up in 2010. Some might feel that Jenny McCarthy was way out of Jim Carrey’s league. However, there are many that feel Carrey was out of McCarthy’s league. Jim Carrey has also been linked to Lauren Holly and Renee Zellweger.

9 David Cross Married To Amber Tamblyn


David Cross and David Beckham have very little in common. One is a hilarious comedian and actor and the other looks incredible in his underwear. Spoiler alert! David Cross is the comedian and actor. However, David Cross and David Beckham have one thing in common besides their name, they attract incredibly gorgeous women. David Cross is a stand-up comedian but has also appeared in several TV shows and movies. From 1995 to 1998, he co-hosted and starred in the sketch series, Mr. Show, with Bob Odenkirk. David Cross is best known for his role as Tobias Funke in the Fox sitcom Arrested Development.

David Cross is married to the gorgeous Amber Tamblyn. She first rose to fame with her role on General Hospital. She has also appeared in The Sisterhood of the Travelling Pants, The Ring, and 127 Hours. David and Amber dated for several years before marrying in 2012.

8 Kevin Hart Married To Eniko Parrish


There is just something about a short and hilarious man that some women just can’t resist. Kevin Hart might be considered average-looking but his wife certainly is not. Kevin Hart is a stand-up comedian and actor. He has released several popular comedy specials, including I’m A Grown Little Man, Let Me Explain, and What Now? He has also starred in several films like Ride Along, Get Hard, and Central Intelligence. He currently stars in Real Husbands of Hollywood.

Kevin Hart is married to the stunning Eniko Parrish. She is a model and is popular on social media platforms such as Instagram. Kevin Hart was previously married to comic Torrei Hart. She claims that their marriage ended because of Parrish. However, Hart denies this. Clearly, Eniko Parrish is far out of Kevin’s league. However, he’s not going to let his height stand in the way of reaching what he wants. Kevin and Eniko made it official when they married in August 2016.

7 Adam Sandler Married To Jacqueline Titone


Adam Sandler might not be the best-looking. He might not also have a muscular body that women can’t stop staring at. However, despite being merely an average in the looks department, with his sense of humor, charm, and personality, he can date any women he’d like. However, it’s not like thousands of beautiful women are trying to knock his door down. All he needed was one beautiful woman to knock his door down. After a successful run on Saturday Night Live, Adam Sandler turned his attention to films and has starred in several memorable movies, including Billy Madison, Happy Gilmore, The Waterboy, and The Wedding Singer.

Adam Sandler is married to the utterly gorgeous Jacqueline Titone. She’s obviously out of his league but he seems not to care. She first appeared in Deuce Bigalow: Male Gigolo starring Rob Schneider. He then introduced her to Adam Sandler who offered her a role in Big Daddy. A year after making the film Little Nicky, they started dating. They married in 2003 and have two daughters together.

6 Howard Stern Married To Beth Ostrosky


“King of All Media” Howard Stern has never been mistaken for a model. In fact, some would say he has the perfect face for radio. However, that hasn’t prevented Stern from dating women hotter that the sun. Howard Stern is a radio host best known for hosting The Howard Stern Show. His show later moved to Sirius XM Radio where it continues to be a big success. He also wrote two books—Private Parts and Miss America. In 1997, Private Parts was turned into a film starring Stern himself.

Howard Stern is one of the most controversial figures in radio and his sense of humor isn’t necessarily for everyone. However, he still manages to date beautiful women. Howard Stern is married to model and host Beth Ostrosky. She is clearly way out of his league but he still managed to end up with her. This gives hope to every funny man in the world. Prior to Beth, he also dated the gorgeous Angie Everhart and beautiful Robin Givens.

5 Judd Apatow Married To Leslie Mann


Leslie Mann is utterly gorgeous and also happens to be hilarious. She’s a perfect 10 that could be with any man she wants. However, she’s not interested in guys with big muscles, a beautiful face, and gorgeous hair. She prefers the classic dad bod, average looks, and hair that takes 5 minutes to comb. Judd Apatow is a director, writer, producer, and comedian. He’s directed several popular films, including The 40-Year-Old Virgin, Knocked Up, and Trainwreck. Leslie Mann has appeared in several memorable films, such as The Cable Guy, Knocked Up, and This is 40.

Judd and Leslie met in 1996 on the set of The Cable Guy. In fact, Judd, a producer on the film, read lines with Leslie during her audition. They married in 1997 and have two daughters together. Leslie has appeared in several films and TV series directed or produced by Judd, including The 40 Year Old Virgin, Funny People, and the TV series Freaks and Geeks.

4 David Spade Dated Heather Locklear


David Spade has never been mistaken for a dreamy Rockstar or beautiful underwear model. Spade is known for his self-deprecating and sarcastic sense of humor. He appears to be average but despite that, he dates women way out of his league. David Spade had his first success on Saturday Night Live. He went on to appear in several popular films, such as Tommy Boy, Black Sheep, and Joe Dirt. He also appeared in the TV series Just Shoot Me and Rules of Engagement.

David Spade dated the smoking hot Playboy Playmate Jillian Grace, and they have a child together. Spade’s list of ex-girlfriends is like a Hottie Hall of Fame. He previously dated Heather Locklear, Brittany Daniel, and Julie Bowen. He was also rumored to have dated Pamela Anderson, Carmen Electra, and Teri Hatcher. In April 2017, Spade was spotted with Glee star Naya Rivera. Rumors quickly started to spread that they’re now dating.

3 Andy Samberg Married To Joanna Newsom


Andy is married to musician Joanna Newsom. Joanna is a singer-songwriter who plays the harp and piano. She has released several albums, including The Milk-Eyed Mender, Have One on Me, and Drivers. Andy is a huge fan of her music and met her at one of her concerts. They soon started dating and got married in 2013. Joanna is slightly out of Andy’s league but he didn’t let something silly like that stand in his way.

2 Russell Brand Formerly Married To Katy Perry


Katy Perry is widely regarded as a smoking hot s*x symbol desired by most men’s fantasies. In fact, Elle magazine once described Katy Perry “as though sketched by a teenage boy.” She has ranked number one on Maxim’s Hot 100 and Men’s Health named her “the sexiest woman.” Most people were shocked when they heard that she married comedian and activist Russell Brand. Many fans and critics felt Katy was way out of his league.

Russell Brand is known for his controversial and outlandish behavior. He first rose to fame as an accomplished stand-up comedian. He has since started in several films, such as Forgetting Sarah Marshall, Get Him To The Greek, and voiced Dr. Nefario in Despicable Me. Brand and Perry started dating in 2009 and was married by 2010. They divorced in 2011 partly because of their conflicting schedules. He has also been linked to New Statesman editor Jemima Khan and model Kate Moss. Since 2015, he has been in a relationship with Laura Gallacher and they have one child together.

1 Seth Macfarlane Dated Emilia Clarke


At one time, the evil genius Stewie Griffin dated the breaker of chains and mother of dragons, Daenerys Targaryen. Seth Macfarlane is best known for creating the enormously popular animated sitcom Family Guy. He also voices several characters in the series, including Brian, Peter, and Stewie Griffin. Additionally, he wrote and starred in the films Ted, A Million Ways To Die In The West, and Ted 2.

Just to be clear, Stewie Griffin didn’t actually date Daenerys Targaryen. In 2012, Seth Macfarlane dated the utterly gorgeous Emilia Clarke. Emilia Clarke is best known for her role as Daenerys Targaryen in the critically and commercially acclaimed fantasy series Game of Thrones. Macfarlane is a huge fan of the series so that was just a bonus. Clearly, Emilia Clarke is way out of Seth’s league but she might have a thing for funny guys. They only dated for about 6 months before breaking up. However, they’ve since remained good friends. Emilia isn’t the only hottie he’s dated. Seth Macfarlane has also been linked to Ashley Greene and Eliza Dushku.

Sources: The Frisky , Men's Health

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