15 Celebs With The Most Impressive Roster Of Girlfriends (2024)

There are just some celebrities out there that have been lucky enough to date some of the hottest women in the industry. It doesn’t matter what movies they are in or what they are like in real life; these guys got something going on because they are able to date women that most men can only dream about.

Some of these men just go from one woman to the next as if they are discarding tissues while some of them have spent a long time with the beautiful women on their list. The problem with Hollywood is that there are beautiful women everywhere. So even when a celebrity is dating a knockout, he just can’t seem to stop looking at all the otherbabes in Hollywood. It’s always something to behold though when we see beautiful women dating beautiful men; we just sit there in awe as we wonder what their children will look like.

These men on our list have been considered very lucky to have dated these women. Throughout their lives, they have dated the most beautiful women in the industry and that’s pretty impressive. Some of these relationships are still going strong while others have crashed and burned. Not that it matters, these guys have some impressive names in their little black books. Check out these 15 celebs with the most impressive roster of girlfriends.

Jared LetoHas A Way With Women

Jared Leto isn’t exactly in the same league as Tom Cruise and Brad Pitt when it comes to his career, but this guy can pull in some pretty gorgeous ladies. He too hooked up with Angelina Jolie when they starred in the movie Alexander together. He had also dated Cameron Diaz for many years, they were even engaged at one point. He’s been linked with so many women that it’s hard to keep track.

When he was a singer, he dated Britney Spears and Jessica Simpson, and when it came to actresses, he dated Scarlett Johansson, Rosario Dawson, Lindsay Lohan, Paris Hilton, and he was even linkedto Sharon Stone.

Allegedly the two met in a bar in 2006 and the rest we will leave to your imagination, but people saw them leaving together.

Jason Sudeikis Is Always With A-List Ladies

We’re not sure how SNL comedian Jason Sudeikis got so lucky, but he has landed himself some beautiful ladies over the years. For one thing, he is currently married to the breathtaking Olivia Wilde.

It’s rumored that he once dated Jennifer Aniston briefly and managed to break her heart.

Don’t get us wrong, he’s not a bad looking guy, but a lot of these women seem to be out of his league. He even tookEva Mendes out for dinner and the two bonded over cigarettes. He’s known as a nice guy, which may be exactly why he’s landing all these beautiful ladies. “He’s a nice, normal guy from Kansas who plays basketball, and his job is to be hilarious and entertaining,” said Rachel Sklar a writer for SNL and who has hung out with SNL cast members. “He doesn’t trash hotel rooms or make sloppy drunk scenes at celebrity hangouts. Sounds like boyfriend material to me.”

Ryan Reynolds Is Living Relationship Goals

Ryan Reynolds has definitely been connected to some beautiful women in the past few years. He is currently married to Blake Lively who is not only one cool chick but who is easily one of the most beautiful women in Hollywood right now. The two play out insane relationship goals on a weekly basis and seem like the perfect couple. Before that, he was married to Scarlett Johansson who is probably every guy’s dream girl. She’s curvy and foxy and can hang out with all the guys. She’s pretty much the perfect woman.

Besides that, he’s been connected to Charlize Theron, and two '90s girls, Rachael Leigh Cook and Melissa Joan Hart. He gave Hart an expensive watch and his heart.

Her response was, "He was 17 and I was, like, 19," she said. "I was like, 'You're too young for me.' So I stopped his car and I wasn't sure; am I going to get mad at him?'" She went on: "I just grabbed him and started kissing him. You get a piece of jewelry like that, you got to make out with the guy!"

Ryan Gosling Dates His Costars

Apparently, Ryan Gosling and Ryan Reynolds get mistaken for each other a lot. They do have one thing in common and that’s the fact that they can snag A-list women all the time. Gosling and Eva Mendes aren’t married, but they might as well be. They have been together for a very long time and they have children together. That’s who he gets to wake up to every morning. Besides that, he’s dated the beautiful Rachel McAdams who he worked with in The Notebook. Those two were such a cute couple.

Gosling also snagged the heart of A-list actress Sandra Bullock even though she was 16 years older than him.

The two were actually together for a while before they broke up. Gosling certainly has had some beautiful women in his life.

Leonardo DiCaprio And All His Models

Every guy in the world probably wishes that he had Leonardo DiCaprio’s life. Not only is he rich and famous but he has dated some of the top models in the industry. The most notable one being with Gisele, the supermodel who retired as almost a billionaire. Many thought he would finally settle down with her but in the end, she moved on because he wouldn’t have babies with her. He was also linked to Blake Lively before she got together with Ryan Reynolds. He doesn’t normally date actresses, but with a girl like Lively, you have to try to make an exception.

Aside from that, it seems he’s been linked to a lot of models including supermodel Naomi Campbell.

DiCaprio’s roster of models is almost limitless.

Sean Penn Dates Leading Ladies

Sean Penn hasn’t been single that much over the years because he spent a great deal of his life married to Robin Wright Penn, a gorgeous actress that has done quite well in the industry. He was also married to Madonna in the early '90s, but they divorced because he was too abusive.

Despitehis rumpled look and his bad reputation, Penn seems to have no trouble drawing in beautiful women.

He’s also been linked to Scarlett Johansson after his marriage with Robin ended. Most recently he was linked to Charlize Theron who is easily one of the most beautiful women in the industry. Some of the women like Theron didn’t stick around for very long and we have to wonder if it had anything to do with the abuse allegations.

Brian Austin GreenDates Foxes

You wouldn’t think that Brian Austin Green could land some of the girls that he has, but he’s been dating pretty much all the girls that other guys crushed on over the years. He stole the heart of Tiffani Amber Thiessen and she’s been in every guys dream since she starred in Saved By The Bell. He also dated the seductive Vanessa Marcil for three years, though aside from beauty, she was probably more in his league career-wise. Austin hasn’t done much outside of Beverly Hills 90210. Seriously, can you even name another movie or show off the top of your head? Yet he managed to date and marry one of thefoxiest girls in the industry, Megan Fox. She may not be the best actress in the industry, but there are thousands of guys out there that would like to take her on a date.

Justin Timberlake Attracts Serious Babes

Justin Timberlake has had some serious women in his life over the years and for the most part, they have been long-term relationships. We all thought he was going to marry pop star Britney Spears because the two just seemed perfect for each other. But instead, he wrote the song Cry Me A River, implying that shebetrayed him.

He was also connected to Fergie for a year. He dated Cameron Diaz for four years and many thought that they would get married.

He went on to hook up with Kate Hudson at a New Year’s Eve party which caused Diaz to be “pissed” at her. He then went on to marry the love of his life, Jessica Biel, another beauty from Hollywood. Judging by the things he has said about his wife, he adores her.

Ashton Kutcher Has A Thing For His Costars

Ashton Kutcher has been linked with some seriously gorgeous women over the years. He’s been linked to some '90s beauties like girl next door Amy Smart and even January Jones for a period of time.

He starred in "Just Married" with Brittany Murphy and the two dated for a year. He said once that he would always consider Murphy to be his first wife.

He met Demi Moore who he was quite a bit younger than but that didn’t stop the two of them from getting married. They were married for almost eight years when Kutcher strayed. Lastly, he’s now married to Mila Kunis, one of the hottest girls in the industry right now. The two have two children together and they are out there making their own relationship goals.

Jake GyllenhaalHas A Thing For Blondes

Jake Gyllenhaal is another guy in Hollywood that can snag a leading lady when he wants to. We’re not sure if this one will ever settle down though, he goes from one relationship to the next and has never been married. He’s dated somegorgeous A-list women that include Reese Witherspoon, Kirsten Dunst, Taylor Swift, and Alyssa Miller.

When asked how many times he’s been in love by Howard Stern, he answered, “three times” before changing his mind to “twice.”

We have to wonder who he changed his mind about. He blames himself though for his relationships not working out and it sounds like maybe he has a fear of commitment. “It was me, man,” he said. “I think I probably just got scared.” He is hoping to find true love one day. “I love love, man,” he said. “Are you kidding me?”

Chris Martin Dates A-Listers

Although Chris Martin is certainly a talented musician, he’s a little quirky. It hasn’t stopped him from pulling in some serious ladies over the years.

He has been connected to other singers like Natalie Imbruglia and Kylie Minogue over the years, but it was his pairing with Gwyneth Paltrow that surprised everyone.

They just seemed like an odd match. Something must have clicked, however because, they were married for a whopping ten years and had two children together. It didn’t work out, however, and when they divorced, Martin went after the girl that is coveted by all men, Jennifer Lawrence. The two weren’t together for very long before Lawrence bailed. Martin is now dating The Tudors actress Annabelle Wallis. Martin has certainly been connected to some gorgeous women over the years.

Ben Affleck Knows How To Steal A Girl’s Heart

Ben Affleck has been stealing A-listers' hearts for years, but he never seems to be able to keep any of them because of his bad behavior. He’s been linked to Gwyneth Paltrow, who seriously has dated a lot of hot guys over the years. He was once engaged toJennifer Lopez, but the two eventually broke up. Many people believed it was because his heart was with Daredevil co-star Jennifer Garner. We all thought that he had finally found his life partner with Jennifer Garner because the two were together for a while and had settled down with children. Affleck’s bad behavior came back to bite him in the behind and he ended upleaving Garner.

John Krasinski Is A Funny Man

John Krasinski is certainly a guy that you wouldn’t expect to be stealing A-lister hearts, but he totally is. He was the dopey nice guy from The Office and that’s kind of how we see him in real life even though he is a really good-looking guy.

“Being funny is one of my greatest strengths. I can make girls smile when they're down, and when they're having a good time, I can carry on the joke.”

He was originally linked to his The Office co-star Rashida Jones. There were also rumors that he romanced Renee Zellweger for a while, but none of that compared to him dating the gorgeous Emily Blunt. She’s not only one of the best actresses in the industry, but she’s stunning and has a pretty cool accent as well. How did he win the heart of this girl?

Tom Cruise Is Charming

We’re not sure if Tom Cruise is ever going to be able to settle down long term. He hasn’t dated anyone significant since his split with Katie Holmes and he may be wondering if there’s anyone that will put up with Scientology. Cruise has been connected with some serious babes over the years. Before Katie Holmes, he was dating the stunning Penelope Cruz for two years.

He’s also romanced Sofia Vergara and Laura Prepon over the years. Then, of course, his marriage to the stunning redhead Nicole Kidman that lasted for quite some time before she bailed.

Cher has even admitted that she had a brief fling with Tom Cruise in the '80s. There’s no doubt about it Cruise can get a leading lady when he wants to.

Brad Pitt Was The Foxiest Man In Hollywood

When you have been dubbed the S*xiest Man Alive twice in your life and you have had four Oscar nominees throughout your career, then you can probably get any girl you want. That’s pretty much been Brad Pitt’s life for many years. Not only was he the golden couple with Jennifer Aniston and then he married one of thesteamiest women alive — Angelina Jolie— but he has some other stunning women on his roster. He’s dated the stunning Claire Forlani as well as longtime love Gwyneth Paltrow.

The two starred in "Seven" Juliette Lewis together and many people believed she was the love of his life. Back in his early days, he was connected with the beautiful Juliette Lewis and every young guy’s crush from Married With Children, Christina Applegate.

It’s safe to say that Pitt has dated some of the best women in the industry.

Sources:www.ranker.com, www.ranker.com