Checkmate & Celebrities: A-List Stars Who Are Obsessed with Chess

For International Chess Day (July 20), we’re diving into the fascinating world of celebrities who love chess — because even the biggest stars can’t resist the thrill of a well-played match.

Chess is a secret obsession for some of the most famous names in entertainment. And at Breakthrough Xclusive, we know that when stars love chess, they bring next-level energy to tournaments, charity matches, and exclusive events.

Want to book a chess-loving celebrity for your next event? Here’s why you should — and who’s already playing the game.

Why Chess is a Good Choice

Chess is a stylish and prestige game of mental dominance. A-listers are drawn to it because here brainpower meets glamour and smart celebs can show what they are.
Nothing beats the tension of a live celebrity chess match: every time the game is a high-stakes drama. Another good point is that such occasion can be of a charity appeal – star-studded chess tournaments raise big money for causes.

And the best part? These celebrities don’t just play — they bring the hype.

Celebrities Who Are Serious About Chess

1. Will Smith – the Prince of the Chessboard

Will Smith compares life strategy to chess moves. When he was a child, his father taught him the game. He then continued training with grandmaster Maurice Ashley. He's really good!

Imagine booking him for a charity chess showdown — now that’s star power.

2. Madonna – the Queen of Pop (and Queenside Castling)

Madonna is a chess fanatic — she’s been spotted playing backstage at concerts and even had a custom chess set made for her Confessions Tour. A Madonna vs. Keanu Reeves chess battle? We can make it happen.

3. Arnold Schwarzenegger – from "Checkmate" to "I’ll Be Back"

Before he became Terminator, Schwarzenegger was a chess player in Austria. The actor once said: “There is nothing like chess to keep the brain smart, and give it a workout”. He still loves the game — imagine him hosting a celebrity chess tournament with a Predator-styl\e twist.

4. Bono (U2) – Rockstar by Day, Chess Mastermind by Night

Bono has called chess "the best game in the world" and plays regularly. He was a member of the Phibsboro chess club in his youth and even met with Garry Kasparov. A U2-themed chess event with live music? Now we’re talking.

5. Keanu Reeves – the Humble Grandmaster

Keanu is a low-key chess lover. He's played competitively in high school and has followed major chess events, like the match between Deep Blue and Garry Kasparov. A John Wick-style chess tournament (minus the guns, of course) would be legendary.

6.  Julia Roberts — America's Sweetheart with a Killer Endgame

The Pretty Woman star is a serious chess enthusiast, often playing between takes on set. Her love for the game is so well-known that directors have written chess scenes into her films. Imagine hosting a charity match with Julia — the combination of her charm and competitive spirit would be box office hit.

7. Nicolas Cage — Method Acting Meets Chess Strategy

The Oscar winner approaches chess with the same intensity he brings to his roles. Cage has been spotted playing in New York's chess clubs. His unpredictable personality would make any exhibition match must-see entertainment.

How to Book a Chess-Loving Celebrity for Your Event

Want to add star ambiance to your chess tournament, charity gala, or luxury brand activation? Here’s how we do it:

· Exclusive matches – pair a celeb against a grandmaster (or another star) for must-see drama.

· Charity auctions – guests bid to play against a famous face.

· VIP chess lounge – A-listers mingle with guests over high-stakes games.

Chess is no longer just a quiet café game — it’s a glamorous, high-profile spectacle when stars are involved.

Want to create the most talked-about chess event of the year? Contact us to book a chess-loving celebrity and make your next move.

Checkmate.