Show Me the Money! 9 Famous High Rollers

Getting your Trinity Audio player ready...

Since the height of the rat pack days in the 1950s, gambling has had a certain allure around it. And even though Frank Sinatra, Dean Martin and Sammy Davis Jr. are long gone, there are many famous high rollers and casino whales out there who are keeping that allure alive.

If you’re not much of a gambler, you might not know what those terms mean.

In casino culture, high rollers and whales are people who play with huge sums of money and sometimes even need to have up to five figures in their wallets just to be seated at certain tables.

It shouldn’t be any surprise then that many high rollers today are celebrities, some of whom use gambling as a second career. Especially if their former careers seem to be in the downturn.

Interested in learning more? Continue reading and we’ll walk you through some of the most famous high rollers playing today. If you are a high roller as well you can also check our page with the best high roller live casinos.

Famous High Rollers Today

Here is our list of some of the most famous high rollers around the globe. Most of them are poker high rollers.

Tobey Maguire

Spiderman is all grown up and he’s now one avid gambler. Among the Hollywood elites, Maguire is recognised as one of the biggest high rollers around.

Phil Hellmuth, a professional poker player who has played alongside Maguire, has said the actor has the talent to go pro if he wanted to. 

In fact, Hellmuth has claimed that the big screen’s first web-slinger may have won millions playing at poker games in private Hollywood residences. 

Ben Affleck

Ben Affleck is one of the hottest names in Hollywood right now. The Oscar winner has shown his talents in acting, screenwriting, and directing.

However, he’s also been recognised for his talents at the poker table. 

In 2004, Affleck played in the Commerce Casino’s California State Poker Championship.

He outlasted 90 other players, including professional poker players, and walked away with hundreds of thousands of dollars in winnings. 

James Woods

James Woods knows a thing or two when it comes to gambling. This is likely in part thanks to roles in films like Casino and The Gambler.

In 2006, he told ESPN’s Bluff Magazine that poker is where the real action in Hollywood is. 

He’s made tens of thousands in poker winnings. 

Norm MacDonald

The comedian, Saturday Night Live alum, and star of his own Netflix show called Norm MacDonald has a Show is one of the biggest A-list gamblers around.

He’s in fact most well known in the gambling world for his rather unlucky losses. 

He famously told Conan O’Brien about one fateful day at the horse tracks. Norm claimed he suddenly woke at 7 am one morning.

He then got in a taxi cab that was labelled taxi #7.

Feeling lucky, he went to the horse tracks and went up to window #7.

He bet $777 on the seventh horse whose name was Lucky Number Seven. “And wouldn’t you know it, the horse came in seventh.”

Shannon Elizabeth

Shannon Elizabeth first hit it big in 1999 when she starred in the wildly successful film American Pie. She then aimed to hit it big again when she became an avid poker player.

In fact, she won tens of thousands of dollars at the 41st Annual World Series of Poker “Ante Up For Africa” event.

She’s said that she’s grateful for doing so well in that event because now everyone thinks “that I’m much better than I am.”

Jennifer Tilly

You may know Jennifer Tilly as the ditsy girl from such films as Liar Liar and Bullets Over Broadway. However, at the poker table, you’ll see that she’s anything but ditsy.

Believe it or not, Ms. Tilly is one of the most successful poker players of all time in the World Series of Poker Ladies No-Limit Hold ’Em.

Satisfied with her winnings, Tilly told papers that she’s planning on playing poker more casually now instead of trying to make a career out of it. 

Gabe Kaplan

Depending on how old you are, you might remember Gabe Kaplan as the star of the hit TV show Welcome Back, Kotter.

After the show ended, Kaplan left the acting world and became a professional poker player.

He’s since won over a million dollars from playing at casinos all over the world as well as in the World Series of Poker. 

Dana White

Dana White is someone who you certainly don’t want to mess around with.

As the president of the mixed martial arts organisation, the Ultimate Fighting Championship, he’s an intimidating figure, to say the least. And the same can be said about this high roller’s poker skills. 

With that said, he’s one of the most well-liked casino customers around. It’s even been reported that he leaves four-figure tips to waiters and six-figure tips to dealers.

If you’re interested in learning how he’s currently doing at gambling, just check out his Twitter feed where he loves to boast about his winnings. 

Charles Barkley

Charles Barkley is one of the most famous athletes-turned-high rollers in the world. He not only aimed to dominate every day on the court but every day at the table as well.

In fact, when Barkley was at the height of his gambling career, he had one goal in mind- win $1m every time he went to the casino. 

He became notorious in Las Vegas as someone who refused to leave the blackjack tables until he either lost or won that coveted million.

One of the admirable things about Charles is that he famously doesn’t play in roped-off areas. He’s satisfied with just playing the small tables and chatting it up with professionals and amateurs alike. 

Learning About These Famous High Rollers

For many people, gambling and poker games can provide a fun escape from the pressures of everyday life.

Learning about the famous high rollers of today and how they play may only add to the glamour and excitement that these games provide. And if you’re lucky, you might one day find yourself playing alongside one of these celebrity gamblers. 

Are you interested in playing live casino games? Check out all the best live dealer casinos.

Related Live Casino Articles