What does it take to be a big time player? If you’ve ever been in a bar or club then you’ve seen the confident men who try to show off their money class. There are the guys you laugh at, metrosexuals with finely pressed suits and collared shirts, flashing money all around. But as much as you and your friends may laugh at the players at the club, they always seem to bring home the most beautiful women. There are players and then there are BIG TIME players with big time game.
In order to nab a celebrity or a beautiful supermodel you can’t just flash some smiles and a few c-notes. No, to be the best of the best you have got to have major game and major cash. There is a select group of older men who pretty much define the term “player.” They strut around with smiles and confidence. They aren’t cocky 25-year-olds who spend large amounts of money to look cool. No, these are defined men who simply sit, smile and speak with the confidence of a king. They are a select group of men and the hippest and hottest of models and celebrity women are there for the taking despite these men getting up there in age.
Some of the men enjoy marrying their new younger prize positions (notable mention to Larry King here). Many of the celebrities on the list are of A-List caliber, the best of the best, and all of them are notorious for being “ladies men.” These men don’t just date beautiful women, they date women who are sometimes decades younger than them. These are 10 Senior Celebs Who’ve Got More Game Than You.
10. Kelsey Grammer – 60 Years Old
Kelsey Grammer got his career kicked into overdrive with his role as Doctor Frasier Crane when he appeared on the hit show Cheers. From there, he thrived on a spin-off of his own, entitled Frasier. The television star and producer has had a tremendous run in Hollywood. Equally impressive is the list of beautiful women he has been seen with over the years. Although he is now married to the beautiful Kayte Walsh (she 25 years his junior), he always seemed to have an appetite for much younger attractive women. In fact, Kelsey Grammer was married to an attractive woman in Camille Grammer (15 years younger) before he cheated on her and impregnated Walsh.
9. David Letterman – 68 Years Old
Funny man David Letterman is best known for driving fast cars and comedy. He has racked up nearly as many speeding tickets as beautiful women he has bedded. In 2009, six months after marrying longtime girlfriend Regina Lasko, Letterman had to fess up to much a much bigger issue than a few afternoon joy rides. The Late Show icon became embroiled in a sex scandal. He was forced to admit on the air, “I have had sex with women who work for me on this show” when news of his affairs and extortion attempts circulated all through the media. Letterman went on Oprah Winfrey’s show to reveal he was still dealing with the fallout from cheating on his wife. Although the actual number of women Letterman had affairs with was never confirmed, it is rumored that Letterman was poaching dozens of beautiful women who worked under and around Letterman on set over the years. The funny man proves he has quite the game (and potential sexual harassment lawsuits brewing too).
8. Patrick Stewart – 75 Years Old
Patrick Stewart took the helm of the Enterprise as Captain Jean-Luc Picard and never looked back. The leader of the Star Trek: The Next Generation was catapulted into stardom. He had a tremendous run in television before starring in the same character on the big screen. Then Picard landed the role of Professor Charles Xavier in the X-Men series and hasn’t looked back since. In addition to his fortune in Hollywood, Picard has done quite well for himself as a ladies man off camera. He has dated numerous beauties, many of them MUCH younger than himself. Jazz singer Sunny Ozell was 37 years younger than Stewart when they dated and actress Lisa Dillon was 39 years younger. Looks like the captain still has got it.
7. Michael Douglas – 71 Years Old
Michael Douglas is Hollywood royalty. His father, Kirk, is well known and successful. His suave son, Michael, has done the family name justice. Michael Douglas was the cool rich Gordon Gekko in Wall Street. In 2000, Douglas’s marriage to Diandra Luker officially ended (separated in 1995). Once “officially” separated, he wasted no time hitting the town. He started dating beauty Martine McCutcheon back in 1998. The author, actress and singer was decades younger and very beautiful. Also in the late 90s, Douglas dated journalist and screenwriter Elizabeth Vargas. Pretty concrete rumors have Douglas and costar Sharon Stone having an affair when they filmed Basic Instinct (I mean, they do basically have actual sex on camera). Other rumors have Douglas having numerous affairs during the course of his failed marriage. Then, in 2000, Douglas married the beautiful Catherine Zeta-Jones despite being 25 years her senior. They have 2 children together.
6. Bruce Willis – 60 Years Old
Bruce Willis’s fame began with the hit television show, Moonlighting. After that, he landed Die Hard and created the legendary John McClane. From there, it’s been a blur of massive A-list success for the actor. Combined with his onscreen success, Willis has enjoyed beautiful women during his run. He married A-list actress Demi Moore in November 1987. After their marriage ended in 2000, Willis enjoyed hitting the town. He is a talented singer and loves to perform in small clubs. The low-key Willis always seems to be safely under the radar when it comes to his love life. Along the way, he dated beautiful actress Brooke Burns (23 years younger) and then married stunning model Emma Heming (also 23 years younger) in 2009. Also on his dating list prior to his second marriage were Aida Yespica and Kim Cattrall.
5. Rod Stewart – 71 Years Old
Rod Stewart and his tight black leather pants. Stewart invented the term “skinny jeans” long before there was such a thing and women loved it. It’s no wonder the British rock legend would easily slide on the list as a ladies’ man. Stewart is known as a procurer of beautiful women. He married model Rachel Hunter in 1990 when he was 45 and she was only 20. The move seemed to ground Stewart for a while but then they divorced in 2006 (although Hunter and Stewart were separated long before). In fact, Stewart was reportedly dating Hugh Hefner’s ex, Kimberley Conrad in 1999. Penny Lancaster then came into the picture. And soon after he was “officially” divorced, Stewart made an honest woman of Lancaster and married her in 2007. She was 27 years younger than him. Regardless, Stewart has admitted he has lost count of the many women he has slept with over his career (what rocker hasn’t).
4. Billy Joel – 66 Years Old
The Piano Man! Billy Joel has been married more than his fair share. It all started with the perfect Christie Brinkley. They were married from 1985-1994. He was in his late 50s when he settled down once again with the beautiful Katie Lee. But after five years (and Katie’s career taking off) the two split. Just this past year, Joel impregnated his girlfriend Alexis Roderick, half his age, and married her. Joel plays a mean piano and he still can nab a beauty half his age. We’re hoping Joel and his new wife have a happy ending. Certainly wedding photos look more like a father giving away his daughter at a ceremony, but to each their own. Joel has always “had a way” with the ladies and it has paid off to the tune of 4 marriages to four beautiful women and counting…
3. Jack Nicholson – 78 Years Old
Jack Nicholson is an amazing actor who has been killing it for decades. In addition to Nicholson’s amazing acting chops he also has been well known to land many beautiful women. The list includes Playboy models, fashion models, singers, actresses and nearly any and all beautiful women that have walked the face of the earth. Here are some highlights: Amber Smith, Angie Everhart (both 3 decades younger than Jack), Amanda De Cadenet, Tracy Richman, Lara Flynn Boyle, Kate Moss, Kelly LeBrock, Heidi Fleiss, and hundreds more. We love you, Jack.
2. Donald Trump – 69 Years Old
Donald Trump proposed to Melania Knauss in 2004, when he was 58 years old and she was 34. The couple married on January 22, 2005 – and they are still married today. This is Melania’s first and only marriage, and Trump has been married twice before. The Donald has managed to nab many beautiful women along the way. His bank account clearly is a big aid, but make no mistake about it, The Donald has some skills. The New York icon has been successful in business and migrated out to television. Now, he is running for President. Trump has become a name brand, a man whose status in the world has far exceeded any normal celebrity. He has great influence in various industries and it’s no wonder he is constantly able to date and marry beautiful models. Here is a highlight list: Ingrid Seynhaeve, Rowanne Brewer, Gabriella Sabatini, Allison Giannini, Kara Young, and Melania Trump (married).
1. Hugh Hefner – 89 Years Old
Nobody can argue that Hugh Hefner is the ultimate Playboy. Hefner started his successful magazine back in the 1960s and hasn’t quit since. He has been surrounded by some of the most beautiful women in the world each and every day of his long and illustrious life. Although these days Hefner has slowed down with aging time, he still strolls around with beautiful women on each arm. Sure it’s easy to label Hefner a sugar daddy who has oodles of money and it’s obviously one incentive for these women to be on his side, but the reality is, Hefner is consistently the ultimate Playboy. There seems to be no end for all the women he is able to bring home to bed. Instead of listing the women he has slept with, we’re just going to assume the number of Playboy bunnies he has bagged is higher than any of us can count. Good for you, Hef. Good for you.
- Ad Free Browsing
- Over 10,000 Videos!
- All in 1 Access
- Join For Free!