25 Most Shameless Womanizers in Movies and TV Shows
25. Jacob Palmer – ‘Crazy, Stupid, Love’
Ryan Gosling plays a modern-day ladies’ man who treats seduction like a refined skill—no cheesy lines, just confidence and style. Bonus points for mentoring Steve Carell’s character in the art of attraction.
24. Joey Tribbiani – ‘Friends’
“How you doin’?” Those three words made Matt LeBlanc’s Joey Tribbiani a sitcom legend. The dimwitted aspiring actor was more puppy dog than predator, making his endless string of dates seem charming rather than sleazy. Though not as calculated as others on this list, Joey’s serial dating made him a quintessential TV womanizer—proof that good looks and confidence can get you far, even if you can’t remember your date’s name.
23. Tony Stark – ‘Iron Man’ / MCU
Before settling down with Pepper Potts, Tony Stark’s black book probably needed its own AI. Billionaire genius + playboy + philanthropist = a lot of press conferences for “unrelated” scandals.
22. Dr. Christian Troy – ‘Nip/Tuck’
A Miami plastic surgeon who uses his skills and the confidence they bring to charm patients and strangers alike. Dr. Christian Troy's womanizing is as much about ego as it is about lust.
21. Schmidt – ‘New Girl’
Before Cece tamed him, Schmidt (Max Greenfield) was a one-man dating app — charming, persistent, and occasionally insufferable. His womanizing came after a dramatic weight loss, giving him newfound confidence and an inflated ego.
20. Sonny Corleone – ‘The Godfather’
James Caan’s Sonny Corleone wasn’t just the hot-headed heir to the Corleone crime family, he was also a man who never let marriage get in the way of his wandering eye. From the very first time we meet him, Sonny is slipping away from the wedding of his own sister to hook up with one of the bridesmaids. His unapologetic philandering is woven into the story, a stark contrast to Michael’s calculated discipline. Sonny’s lust was as uncontrollable as his temper, and just as likely to land him in trouble.
19. Jason Stackhouse – ‘True Blood’
In the supernatural soap opera that was ‘True Blood,’ Jason Stackhouse, played by Ryan Kwanten, was the hot-but-dumb archetype—a small-town himbo with a six-pack and an endless libido. While vampires schemed and shapeshifters brooded, Jason was busy sleeping his way through Bon Temps. His conquests included waitresses, fangbangers, and occasionally women with questionable supernatural ties.
18. Alex ‘Hitch’ Hitchens – ‘Hitch’
Will Smith’s “date doctor” is a professional womanizer, using his powers for… well, money. His job? Helping men woo women, but his real charm is in the execution—smooth, calculated, and dangerously good at reading people.
17. Chuck Bass – ‘Gossip Girl’
Rich, smug, and scandalously dressed, Chuck Bass (Ed Westwick) made seduction his sport. Between breakups with Blair Waldorf, Chuck filled his dance card with anyone who caught his eye, proving that arrogance, when paired with power, can be dangerously attractive.
16. Dan Fielding – ‘Night Court’
A sleazy attorney who hits on anything in heels. His charm is questionable, but somehow, it works often enough to keep his ego inflated.
15. Connor – ‘Ghosts of Girlfriends Past’
Matthew McConaughey plays a modern Scrooge of love, haunted by exes who force him to confront his shallow ways. Rom-com morality at its finest.
14. Nick Marshall – ‘What Women Want’
Mel Gibson plays an ad exec who knows how to sell—both products and himself. After a freak accident lets him hear women’s thoughts, he realizes he’s been a total sleaze and starts to change… kinda.
13. Dr. Mark Sloan – ‘Grey’s Anatomy’
Plastic surgeon with abs and charm to spare, Eric Dane as Seattle Grace Hospital’s doctor “McSteamy” was the resident ladies’ man. Sure, Lexie made him change his ways, but there’s no denying his womanising past.
12. Arthur Fonzarelli – ‘Happy Days’
The Fonz (Henry Winkler) is the epitome of cool—leather jacket, slick hair, and the ability to summon women with a finger snap. He’s TV’s original cool-guy womanizer.
11. Vincent Chase – ‘Entourage’
Vinny Chase, played by the ever-smooth and suave Adrian Grenier, is what happens when a good-looking kid from Queens becomes a Hollywood star overnight. Surrounded by fame, money, and willing women, Vinny indulges without much thought—a glossy depiction of fame’s temptation.
10. Trent Walker – ‘Swingers’
Vince Vaughn’s nightlife-loving character in ‘Swingers’ mentors a heartbroken Jon Favreau in the art of picking up “beautiful babies” during the swing revival of the ‘90s. Could the character sketch be more cliched?
9. Frank T.J. Mackey – ‘Magnolia’
Tom Cruise as a motivational speaker teaching men to “seduce and destroy” is peak toxic masculinity. His seminars are part sales pitch, part therapy session, for him and his followers. An absolute chauvinist!
8. Sam Malone – ‘Cheers’
A bartender. A retired pro baseball player. A head of hair so perfect it deserved its own credit. Sam Malone (Ted Danson) was the ultimate ‘80s ladies’ man. While his one-night stands were plentiful, Sam’s long-running romance with Diane gave him depth beyond the bar’s backroom antics. His womanizing was textbook—charming, cocky, and dangerously addictive.
7. Hank Moody – ‘Californication’
Hank Moody, portrayed by the dangerously charming David Duchovny, is what happens when you mix self-destruction, literary talent, and an LA party scene. A brilliant writer perpetually stuck in a creative rut, Hank loves his ex-wife deeply but can’t resist temptation, especially when women literally throw themselves at him. His bad decisions come as naturally as his wit, and audiences couldn’t stop watching the trainwreck.
6. Giacomo Casanova – ‘Casanova’
The original seducer, immortalized by Heath Ledger in a performance that blends danger and charisma. This Casanova navigates 18th-century Venice’s pleasures and perils with equal skill.
5. Barney Stinson – ‘How I Met Your Mother’
Suit up! Barney Stinson (Neil Patrick Harris) is the lovable sociopath of the dating world. Scarred by heartbreak as a teen, Barney transforms himself into a confident, suit-wearing Casanova with a “Playbook” of absurd seduction tactics. He’s manipulative, shallow, and morally bankrupt, but also cartoonishly over-the-top, which made audiences forgive him. Whether faking injuries for sympathy or staging elaborate ruses, Barney turned womanizing into an art form.
4. Alfie Elkins – ‘Alfie’
Both Michael Caine and Jude Law’s portrayals make Alfie a charming but emotionally hollow playboy who speaks directly to the audience about his conquests. Eventually, even Alfie realizes the emptiness of his lifestyle.
3. James Bond – ‘James Bond’ Franchise
James Bond prefers his martinis shaken, not stirred, and he's never alone. The world’s most famous spy racks up as many lovers as he does kills, often in the same 24 hours. His charm is as deadly as his Walther PPK.
2. Don Draper – 'Mad Men’
If charisma could be bottled, Jon Hamm’s Don Draper would own the patent. The Madison Avenue ad man is as iconic for his affairs as his ad campaigns. Haunted by a traumatic childhood, Don uses women to fill an emotional void he can’t articulate. Secretaries, clients, strangers—all fair game. His liaisons were often as much about escape as pleasure, making him one of TV’s most complicated womanizers.
1. Charlie Harper – ‘Two and a Half Men’
Charlie Harper is the embodiment of the Hollywood bachelor fantasy—oceanfront home, steady income from jingles, and an endless parade of one-night stands. His world flips when his uptight brother Alan and his young son Jake move in, forcing Charlie to balance parenting moments with his…well, extracurricular activities. He’ll hit on anyone: women in bars, his neighbor Rose (borderline stalker), or Jake’s teachers. Armed with terrible pickup lines and zero shame, Charlie became TV’s king of womanizers, and made Charlie Sheen the highest-paid actor on television at the time.
