Ladies' Men: 'Don Jon' and Other Movie Playboys We Love

By Tyler Doupe

With Don Jon – the story of a perpetual ladies' man who finds more gratification in watching Internet pornography than actually being with a real women - gearing up to hit the big screen on September 27, we’ve opted to revisit some of the most notorious on-screen playboys from the cinematic past and present. Feast your eyes upon 11 of the most prolific ladies' men of our time.
James Bond

James Bond has probably had more women than most men would know what to do with. He seems to manage quite nicely, though. If James Bond existed outside of the silver screen or the pages of Ian Fleming’s novels, the man would most likely have every STD known to man and perhaps even some of unknown origin. But given that he is a fictitious character, he can charm his was into the short-lived loving embrace of just about any woman that crosses his path.
Drayton Jackson from How to be a Player

Though the film was fairly chauvinistic and not terribly well made, it would be an understatement to say that Drayton Jackson (Bill Bellamy) wrote the book on, well, how to be a player. The film found his devious, philandering ways eventually catching up to him, but not before he courted half the female population in his city.
Indiana Jones

Though he was the bookish type, archaeologist Dr. Jones was a major hit with the ladies. In the original trilogy, he was a love ‘em and leave ‘em kind of guy, but eventually Marion Ravenwood (Karen Allen) of Raiders of the Lost Ark made an honest man out of Indy in The Kingdom of the Crystal Skull.
Bruce Wayne

The Caped Crusader’s more sedentary alter ego was and still is not shy around women. He’s had trysts with Rachel Dawes, Vicki Vale, and that’s just to name a few. The billionaire playboy just isn’t quite ready to be a one-woman kind of man. Perhaps the trauma of losing his parents at such a young age has made the man cautious of any type of long-term commitment; or maybe fighting crime occupies so much of his free time that he doesn’t feel ready to settle down.
Leon Phelps: The Ladies Man

As his title tells us, Leon Phelps is a big time ladies' man. He is a radio-program host that offers listeners tips on how to close the deal. Phelps is one of two characters on our list to originate from a Saturday Night Live sketch, Tim Meadows really owned the Leon Phelps persona and exuded vintage sex appeal in a farcical, over-the-top kind of way.
David Wooderson from Dazed and Confused

In the retro stoner comedy Dazed and Confused Matthew McConaughey plays the role of a past-his-prime burnout trying to relive his high school glory days with such precision that much of his dialogue is still regularly quoted to this day. David has a way with women and a thing for young girls and redheads. And he certainly doesn't like to take no for an answer.
Ron Burgundy

A proud chauvinist and major a-hole, Ron Burgundy was quite the ladies' man – at least in his own mind. Burgundy was a confident news anchor that found himself threatened by the arrival of his new coanchor Veronica Corningstone. Look out for the sequel hitting theaters December 20.
Austin Powers

God only knows what women see in this superspy that is cryogenically frozen in the ‘70s and released in the present, but whatever it is, he has them eating out of his hand in no time. Though Vanessa Kensington managed to tame Agent Powers for a moment, we all know how that ended. Naturally, Powers was unfazed and on the prowl in no time after discovering his onetime love was a Fembot.
Roger Thornhill in North by Northwest

In life, Cary Grant may have been one of the last stars to possess that ‘Old Hollywood’ glamour. In Alfred Hitchcock’s tale of an extreme case of mistaken identity, Grant’s character, Roger Thornhill, was a career playboy with charm to spare. However, in the end, even Roger Thornhill wasn’t immune to the charms of the lovely Eve Kendall (Eva Marie Saint) in North by Northwest.
Sebastian from Cruel Intentions

In one of his first breakout roles, Ryan Phillippe portrayed Sebastian Valmont, a ladies' man that took courting women to a sadistic and often evil place. When he makes a bet with his stepsister that he will sleep with a virgin that is saving herself for marriage, their sadistic bet begins to hurt all of the parties involved. And Sebastian finds that he is in too deep when he actually begins to develop feelings for his target. The film is very loosely based on Dangerous Liaisons.
The Butabi Brothers from A Night at the Roxbury

They were ladies' men at heart, although they failed miserably at actually closing the deal. The Butabi Brothers tried to get into the right clubs, thought they employed the right moves, believed they had the wardrobe, and did have the tenacity to try to dance their way into the hearts of ladies everywhere. But unfortunately for them, there weren’t many ladies that were buying their brand of debonair.

Check out Don Jon in theaters Sept. 27.