15 Lucky Men Who Have Dated The Hottest Women Alive

Some men just seem to have all of the luck. They drive fast cars and live in mansions. Their bank balance ensures that they can have whatever they want, whenever they want it. On top of all of this, they also get to spend time with some of the hottest women in the universe.

Victoria’s Secret models, A-list actresses, fiery singers – the men in this list are lucky enough to have done it all. Some of them are talented and handsome in their own right, able to attract beautiful women thanks to their own star status. For the others, it’s simply the ring of cash in their pockets that brings them the kind of dates most guys can only dream of.

It’s hard to like a man who has been in a relationship with one of the most gorgeous models of all time – and then ditched her for another. How do they do it? We’d pay to know!

Take a look at our list of 15 men who can truly boast of having dated the hottest women alive. A few of them even bagged one or two for the long term, getting hitched for good measure. If you wouldn’t kill to be one of these men, then you’re lying to yourself. Prepare to be green with envy!

15 Johnny Depp

By this time, we’ve all heard the gory details of Depp’s recently failed marriage to beautiful Amber Heard. Before that, he was in a long-term relationship with Vanessa Paradis, the father of his children. But before that? Go back further and you find that Depp was a bit of a lady’s man, with plenty of notches on his belt. He was a fixture in Kate Moss’s life when she reached her heyday, and he had to have a tattoo altered after splitting up from then it-girl Winona Ryder. He also has rumoured links with Christina Ricci, Naomi Campbell, and a few other stars.

14 Tom Brady

There’s nothing like an upgrade every now and then. That must have been what was going through Tom Brady’s mind when he got divorced from model Bridget Moynahan. He didn’t waste much time at all before he moved on to his next flame, who just happened to be a supermodel. That was Gisele Bundchen, and she is now his wife, too. Whatever his technique may be, it’s clear that it works for the long-term – or at least, longer than a few of the guys on this list! If he happens to split up with Gisele in the future it’s hard to image where he could go to aim even higher than her.

13 Matthew McConaughey

He might be married to Camila Alves right now, but McConaughey was one of those bachelors who strung together a long list of lady loves in front of the paparazzi cameras. Take a look at his dating history before meeting Alves in 2007, and prepare to get jealous. His ex-flings include the incredibly gorgeous Penelope Cruz, A-listers like Sandra Bullock, and even names you wouldn’t expect at all, like Janet Jackson. Yes, that Janet Jackson. It seems bizarre to think of it now, but clearly he was able to bat above his weight before he really got on our radars as a fantastic actor.

12 Mark Wahlberg

He may now be settled with his wife Rhea Durham, a model who is now also the mother to his children, but that wasn’t always the way. Between his fledgling music career and his rather more successful time as an A-list actor, Marky Mark has spent a lot of time with beautiful women on his arm. These have included models like Rachel Hunger and Frida Andersson. Given his dark past, it almost doesn’t seem fair – but with leading man charm, clearly he’s able to win over women that would be beyond most men. That’s the way it goes when you’re rich and famous!

11 Bruce Willis

For a balding, scary-looking guy, Bruce Willis has done pretty well for himself – and not just in the world of cinema. He’s definitely got a thing for models, as you can tell fairly easily from his dating history. Brooke Burke, Maria Bravo Rosado, and Emily Sandberg are all on his list of ex-flames, but he has now finally settled down with model and actress Emma Heming. It’s fairly clear that he’s pleased as punch to have bagged this younger lady as his wife! We don’t blame him – how many men his age could attract a young and gorgeous model like her?

10 Adrian Grenier

You may recognize Adrian Grenier from his turn in Entourage, and although the show achieved an almost cult status even while airing, he hasn’t really done much since to put his name on the A-list. But somehow he manages to bag some seriously hot ladies – it must be his natural charm! He obviously has a bit of a thing for models, judging by his list of exes. These include swimsuit model Melissa Keller as well as Emily Caldwell, known for her work both in front of and behind the lens. There’s also Courtney Robinson, Isabel Lucas, and allegedly Courtney Bingham.

9 Alex Rodriguez

For a baseball player, Rodriguez has some serious pulling power. And we mean serious. There’s no other man on this list who can boast of dating quite so many A-listers whilst being a “mere” sports star themselves. Want to know who is on his list? Well, it’s a lot of golden haired beauties. Cameron Diaz, Kate Hudson, and Madonna are all names that he has been linked with. Perhaps he just really loves getting invites to the biggest award shows in the entertainment industry. Then again, he’s also dated Torrie Wilson, former Miss Universe and Playboy model-turned WWE wrestler.

8 Ryan Phillipe

For a guy whose biggest claim to fame is mostly being married to Reese Witherspoon, Ryan sure has dated a hell of a lot of beautiful women. Reese herself helped him to become half of a very hot power couple in early days, when both of them were launching huge acting careers. Nowadays his star may have faded, particularly compared to his ex-wife’s, but he might not be complaining too much. His dates since then have included blonde bombshells Abbie Cornish and Amanda Seyfried. It seems like being a divorcee suits this guy right down to the ground if his post-split stats are anything to go by.

7 Adam Levine

Whatever your opinion on Adam Levine’s music may be, you have to admit that the guy has style. He has made it a policy to only date Victoria’s Secret models, and since those are generally the hottest girls you will ever see, it’s a pretty good policy. He was linked with Nina Agdal, Anne Vyalitsyna, and Angela Bellotte in the past. Of course, that was before he settled down and married Behati Prinsloo, who is, of course, a Victoria’s Secret Angel. There’s nothing like making a decision and then sticking to it. Way to go, Adam! Tell us your technique?

6 Orlando Bloom

Given his pretty boy looks, it’s probably no surprise that Orlando Bloom has managed to net some seriously gorgeous women. He has a lot of rumoured hook-ups to his name, like Nina Dobrev, Carolina Guerra, Liv Tyler, Selena Gomez, and Naomie Harris. The ones we know are true? A marriage to Miranda Kerr, as well as dates with Sienna Miller, Kate Bosworth, Vanessa Lachey, Luisa Moraes, and – most recently – Katy Perry. While he may not act as much as he did in his brief heyday of roles, he certainly keeps his name in the papers with these regular rotations of gorgeous dates.

5 George Clooney

George has always been a little bit of an odd one. Unlike most A-list actors, he doesn’t bother to date other actresses – and in fact, doesn’t usually go for celebrities at all. Somehow that almost adds to his charm, as if any woman could imagine herself bumping into him one day and catching his eye. Well, any ridiculously talented and smart woman, that is. The unknown but super hot women he has dated include Stacy Keibler, Elisabetta Canalis, and Celine Balitran. He shocked the world of entertainment by actually getting married to Amal Clooney, who just happens to be a stunning lawyer.

4 Jason Statham

3 Derek Jeter

Derek Jeter has dated so many of the hottest women around that we could spend this whole article just talking about him - Jessica Biel, Vanessa Lachey, formerly Minnillo, Jordana Brewster, Gabrielle Union, Mariah Carey, Vida Guerra, swimsuit model Bridget Hall, and Adriana Lima, for god’s sake. It only gets worse – Scarlet Johansson, Lara Dutta right after she was crowned Miss Universe, Jessica Alba, and finally, Victoria’s Secret model Hannah Davis. Basically, if you can think of an actress or model who you consider to be hot, then Jeter’s probably already been there.

2 Leonardo DiCaprio

Oh, Leo. What a man. Most of us would only ever be able to dream of leaving a legacy like his. Where most famous men aim for models, that’s not enough for Leo. No, he’s only content with going right the way to the top, subsisting on a diet of supermodel. Gisele Bundchen, Bar Rafaeli, and Victoria's Secret Angel Erin Heatherton have all been pictured on his arm, though he tends to show up at awards ceremonies and events alone. It seems that there’s still no taming this bachelor, who might possibly be the most eligible in the world – particularly after his Oscar win.

1 Hugh Hefner

You probably knew this one was coming, but if anyone can lay claim to dating the most hot models of all time, it has to be good old Hugh. From his position in the Playboy mansion, he has dated huge amounts of women, often multiple of them at once. He has a veritable harem living with him, and most of them also tend to grace the pages of his magazine empire. We would try listing them all, but with over 68 names on his list – most of them between the ages of 18 and 30 at the time of their relationship – there’s just not enough space on the page. Notable recent highlights include twins Karissa and Kristina Shannon.

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15 Lucky Men Who Have Dated The Hottest Women Alive