Hollywood Actors Who Made Big on Gambling

While they’re best known for acting on the national or global stage, many Hollywood actor hobbies follow the same path as ours do. Gambling is one such pursuit, where a few popular names find their place as either major enthusiasts or big winners. Taking a look at three of the biggest wins and the most dedicated players, we want to explore just who of these famous names stands out above the rest.

Sean Connery

James Bond is no stranger to betting, and neither it seems was Sean Connery. Well known for his love of gambling over the decades, Connery first took on the Bond character in 1962 with Dr. No, according to a major Sean Connery fansite. Apparently having taken the lessons of the spy to heart, the very next year he would put Bond’s famous luck into action.


Custom Personal Gift Bond Collage Test” (CC BY 2.0) by Howdy, I’m HMK

Heading to the Casino de la Vallee in Italy in 1963, Connery placed his bet on 17, the actor’s lucky number. While the first spin ended with a bust, the second spin landed, followed by the lucky hits on the third and fourth spins. Walking away with the equivalent of $27,000, beating the odds of 1:50,653 is a decidedly Bond thing to do.

Jennifer Tilly

Famous for her role in the Chucky movies, Jennifer Tilly has often been typecast as a bit of an airhead, but this couldn’t be further from the truth. In real life, Tilly is an accomplished poker enthusiast who ranks as one of the best female players in the world. As noted by the LA Times, Tilly eventually preferred poker to acting, and with good reason.


Jennifer Tilly” (CC BY-ND 2.0) by World Poker Tour

Over her career, Tilly earned a bracelet from the World Series of Poker and brought home more than $900,000 in winnings. Recently pivoting to online games, Tilly remains successful, though we’ve been unable to pin down where exactly she plays. As a savvy player, odds are she searches for the biggest bonuses like those from the CasinoSmash selection of the best NJ online casinos. After all, deposit matches, free spins, and professional reviews would give her less time wasted and more time at the tables.

Ben Affleck

Because winning a couple of Oscars isn’t enough, Ben Affleck has also long been a fan of poker. Though rumors persist of his work in friendly games with other celebrities, the actor and screenwriter is better known for making the World Poker Tour finals in 2004. Bringing home $350,000 in a single game is a hell of a payday, even for an actor who regularly commands millions from his acting and directing career.


Ben Affleck” (CC BY-SA 2.0) by Gage Skidmore

Making it big in Hollywood is about skill, talent, and hard work. Just as important to many big names, however, is the element of luck. While the above Hollywood actors have proven that they have what it takes to keep the world entertained by their on-screen antics, their luck in the gambling realm is also a thing of legend. Whether releasing hit movies or beating the odds on a table, one thing’s for sure, we wouldn’t bet against them.

Updated: March 8, 2022 — 2:51 pm