13 Celebs Who've Dated Hollywood's Sexiest Women

Hollywood celebrities are infamous for jumping into the sack with no preamble and just as quickly, discarding their significant others as easily as a piece of used tissue. And for this reason, broken relationships, separation, and divorce run rampant in the entertainment world. It’s all in the circumstances really, because celebs are surrounded by so much temptation and superficiality. And because birds of a feather flock together, it’s but natural that these beautiful people gravitate towards equally beautiful people from the same industry.

Many male celebrities have been deemed crazy lucky by the public for having landed some of the most desirable women in Hollywood at one point in their lives or another. Some relationships have stood the test of time (at least by Hollywood standards) and others fizzled out as quickly as they started. But the fact of the matter is, these men have had the privilege of putting the names of the sexiest women in Hollywood in their little black books.


13 Jason Sudeikis (engaged to Olivia Wilde)

Many may arguably call the relationship of Jason Sudeikis and Olivia Wilde a case of beauty and the geek. Sudeikis is a known comedian and sketch writer for Saturday Night Live while Wilde is one of the hottest women in Hollywood, with her lustrous brown locks and mesmerizing cat-like eyes, coming into prominence in the TV shows, The OC and House, and movies like Tron: Legacy and Her. Sudekis and Wilde became engaged in 2011 and Wilde was pregnant with their son in 2014, strutting the red carpet during awards shows with her sexy baby bump on display.

12 Jay-Z (married to Beyonce)

There’s no doubt about it, Jay-Z is considered one lucky man for being married to a woman as beautiful, sexy, and talented as Beyonce. For the longest time, the power couple kept their relationship under wraps, neither confirming nor denying if they were really dating. They caught the media and public by surprise when reports leaked that they married in secret in April of 2008 and even then, they were still fiercely private about their personal lives. It’s only in the last couple of years that they’ve become a little more lax, especially after their daughter, Blue Ivy was born.

11 Sean Penn (dating Charlize Theron)

Sean Penn has always courted controversy with his acerbic tongue and his very colorful personal life. But this hasn’t stopped the ladies from flocking to him. His first wife Madonna was head over heels for Penn and his marriage to second wife Robin Wright lasted for a good 14 years, despite its ups and downs. And since early 2014, Penn has been dating one of Hollywood’s sexiest, Charlize Theron. Theron, who made her breakthrough performance in The Devil’s Advocate, has established herself not just as a serious actress, but as a fashion icon, always topping the best dressed list at red carpet events.

10 Brian Austin Green (married to Megan Fox)

Despite the fact that he’s done many other bit roles in the recent past, Brian Austin Green will always be known as geeky David Silver in the original Beverly Hill 90210. When Megan Fox caught every man (and woman’s) attention as hottie Mikaela Banes in the movie Transformers, many wondered if she was seeing anyone. And it came as a surprise when the media reported that Fox had been dating Austin Green for the last three years, simply because it seemed like such an unlikely pairing. But having married in 2010 and produced two sons, it’s apparent that the couple is a happy one.

9 Andrew Garfield (dated Emma Stone)

Fans of Andrew Garfield and Emma Stone wanted to cry buckets when news broke out that the couple had split up. The couple dated for over three years, having met in the set of The Amazing Spider-man. Garfield had not made his mark in the entertainment industry before the Marvel film series, but rose to fame after he effectively portrayed Peter Parker and alter-ego Spiderman. He hit the jackpot when he accepted the role, because not only did he become part of a blockbuster franchise, but he also snagged one of Hollywood’s most sought-after leading ladies.

8 Justin Timberlake (dated Cameron Diaz, married Jessica Biel)

Justin Timberlake is known not to have dated just one, but two of Hollywood’s hottest women. Three if you count Britney Spears, but they were both just kids then, so we’re not too sure if she counts. Apparently not being one to mind big age-gaps, Timberlake went on to date super sexy Cameron Diaz, eight years his senior. The relationship lasted for a good three years before he moved on and began seeing Jessica Biel just a month after his break-up with Diaz. Timberlake and Biel, who’s known for her stint in the TV show, 7th Heaven as much as she’s recognized for having a killer body, are dubbed as one of Hollywood’s most endearing couples. Having married in 2012, they recently welcomed their first child with open arms.

7 Ashton Kutcher (married Demi Moore, engaged to Mila Kunis)

He regaled audiences with his comedic prowess in That 70s Show, which was where he met his current fiancé and baby mama, Mila Kunis. But their relationship didn’t blossom until years after the show ended. Before Kunis, Kutcher gave rise to the term cougar when he married Demi Moore, 15 years his senior. This started a trend in Hollywood of older women hooking up with much younger men. But like most Hollywood marriages, theirs didn’t last. They divorced after eight years of marriage and Kutcher has since moved on with Kunis.


6 Jake Gyllenhaal (dated Reese Witherspoon and Taylor Swift)

He’s not just gorgeous, he’s also lauded as a serious actor and it’s but natural that Jake Gyllenhaal is drawn to women who are just as successful and just as attractive as he is. He was in a relationship with Reese Witherspoon for around two years. When that fizzled out, he famously dated Taylor Swift, albeit briefly. Rumor has it that he basically trampled on her heart, making him just one of the many ex-boyfriends that Swift wrote a song about. It’s said that her hit song, Shake It Off is about her feelings towards Gyllenhaal post break-up.

5 Chris Martin (married Gwyneth Paltrow, rumored to be dating Jennifer Lawrence)

Everyone thought that the marriage of Chris Martin and Gwyneth Paltrow was the stuff dreams were made of. Clearly in love and committed to making the marriage work, it came as a shock when the pair announced their “conscious uncoupling” after more than 10 years of marriage. But it looks like the couple is on very friendly terms, perhaps for the sake of their two children. In fact, Paltrow doesn’t seem to mind that Martin is allegedly dating another Hollywood beauty, Jennifer Lawrence. Despite the age gap, Martin and Lawrence are rumored to be seeing each other, but taking things slow.

4 Ryan Reynolds (married Scarlett Johansson, then Blake Lively)

He’s come a long way from his career beginnings, when he starred in the TV sitcom, Two Guys and a Girl. Today, Ryan Reynolds is one of Hollywood’s most in-demand actors. He started dating sultry actress Scarlett Johansson in 2007, though they kept a very low-profile, rarely being photographed in red carpet events and movie premiers together. They quietly married in 2008, but divorced in 2011. While still married to Johansson, Reynolds met Blake Lively on the set of the film, Green Lantern and the two began a relationship in 2011. It's unclear if Lively was the cause of his divorce from Johansson. Whatever the case, Reynolds and Lively are now blissfully married and parents to a lovely baby girl. Johansson herself is engaged and a new mother as well.

3 Ryan Gosling (dated Sandra Bullock, Rachel McAdams, and Eva Mendes)

He’s considered one of the hottest men in Hollywood and as clichés go, he’s been in relationships with some of Hollywood’s sexiest ladies. Ryan Gosling seems to have a penchant for dating older women, his first publicly known relationship being with Sandra Bullock, 14 years his senior, but still considered one of the most gorgeous women in the entertainment industry. He then famously dated his The Notebook co-star Rachel McAdams, who’s two years older than the Canadian-born hunk. Presently, he’s in a relationship with sultry Eva Mendes, seven years his senior, and by whom he has a daughter.

2 Ben Affleck (dated Gwyneth Paltrow, engaged to Jennifer Lopez, married Jennifer Garner)

Ben Affleck’s love life has always been tabloid fodder, most likely because he’s dated a bevy of beautiful famous women. He was in a relationship with Gwyneth Paltrow for three years, though the two are still friends to this day. Afleck then got involved with Jennifer Lopez in a much-publicized relationship that eventually took its toll on their engagement. They called off the wedding four days prior to the big date, then ended the relationship for good a few months later, blaming the media for the break-up. But today, Afleck happily has himself another Jennifer—his wife of almost 10 years, Jennifer Garner, by whom he has three children.

1 Brad Pitt (dated Gwyneth Paltrow, married Jennifer Aniston, then Angelina Jolie)

He’s been considered one of Hollywood’s sexiest men for nearly three decades and at 51 years old, Brad Pitt still has that appeal that makes women swoon. So is it any surprise that such a specimen has dated women who are equally appealing? Many may have forgotten that he was once engaged to Gwyneth Paltrow, whom he met on the set of the film, Seven. He purportedly broke Paltrow’s heart when the engagement ended, but he didn’t waste time in moving on. He began dating Jennifer Aniston a year later and the two married in 2000. Of course, we all know how and why that marriage eventually ended. Pitt admitted that he fell in love with Angelina Jolie on the set of the film, Mr. and Mrs. Smith, when he was still very much a married man. Needless to say, he ended things with Aniston before he started up with Jolie, who is the mother of his six children.



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