Chess isn’t just for grandmasters, nerds, or your uncle who insists he “let you win.” It’s been turning up in far stranger places - tucked under the arm of a billionaire, spread across a film set, or even between a naked woman and a world-famous artist.

In this article, we’re not talking about tournament players. We’re talking about actors, musicians, athletes, business moguls, and cultural icons who found themselves - sometimes awkwardly, sometimes brilliantly - across a chessboard.

Some played seriously. Some just posed.

But each of these moments says something about chess: its symbolism, its mystery, and its weird habit of showing up wherever humans chase status, beauty, or meaning.

In 1963, 20-year-old artist Eve Babitz played a nude game of chess against Marcel Duchamp — the legendary French conceptual artist and devoted chess player - at the Pasadena Art Museum. The photo became an icon of art, defiance, and the strange allure of the chessboard (source).

What Famous People Actually Play Chess?

When you hear that Albert Einstein, Benjamin Franklin, or even Napoleon Bonaparte played chess, it’s not exactly shocking. These were brilliant, strategic minds – the kind you expect to be drawn to the game.

But what if we told you that Arnold Schwarzenegger brings a board to movie sets, Madonna trained with a chess master, Lewis Hamilton calls it his second favourite sport, and AFL star Jesse Hogan got so hooked he now plays every day?

Arnold Schwarzenegger - The bodybuilder, movie star, and former Governor of California has long been a fan of chess. Arnold learned the game from his father and later made it part of his routine in America, often playing in between sets at the gym. He’s described chess as “the ultimate workout for the mind” and even played a televised match against Mike Tyson. For Arnold, the game isn’t just strategy—it’s discipline, focus, and fun. He has supported chess events, including the Arnold Classic Africa Chess Tournament.

In these incredible photos, we see Arnold Schwarzenegger playing chess with World Champion Garry Kasparov, facing off against Mike Tyson in a heavyweight match, giving a simultaneous exhibition like a true master, and even sharing a game with his pet donkey Lulu

Madonna didn’t just dabble in chess – she went all in. In the early 2000s, she became known for playing thousands of games online under her own name and even hired Scottish chess champion Alan Norris as her private coach. The Guardian called her a “weather vane for modern life,” saying her interest in chess reflected a cultural shift toward valuing mental fitness. She also wove chess into her creative work – most notably in The Power of Good-Bye music video, which features an emotional chess game.

Madonna plays a symbolic chess game in The Power of Good-Bye music video – a visual metaphor for love, loss, and control.

It turns out Madonna wasn’t the only glamorous woman with a serious love for chess. Marilyn Monroe, often underestimated, reportedly found peace of mind in the game and owned multiple expensive chess sets. Lauren Bacall was photographed playing with her husband Humphrey Bogart, a dedicated tournament-level player. And Julia Roberts, not exactly the first name you’d associate with chess tournaments, reportedly played over 10,000 online games, peaking at a rating of 2057 - well above casual level. She’s said that chess helps her keep her mind sharp and teaches patience and strategic thinking. This is a gentle reminder that attractive people are allowed to play this game too! 

Lauren Bacall and Humphrey Bogart shared more than just on-screen chemistry, they were both avid chess players - Bogart, once known to hustle games for cash and they even appeared together on the cover of Chess Review in 1945

And what about the boys? When we hear “chess player,” most of us picture an older guy hunched over a wooden board, deep in thought. But chess isn’t just an old-school pastime anymore. These days, it lives on phones, streams, TikToks which means anyone can play! As it turns out, some of the world’s best athletes are avid chess players. Lewis Hamilton credits chess with helping him stay calm and improve strategic thinking under pressure, he even played regularly with Charles Leclerc during the F1 season. AFL star Jesse Hogan became “stone cold addicted” to chess within a month of learning, describing it as a way to sharpen focus and relieve pressure during matches and saying he genuinely enjoy it. Boxing legend Lennox Lewis spoke on The Joe Rogan Experience about playing chess on daily basis to keep is mind active. Icelandic strongman and Game of Thrones actor Hafþór Björnsson (aka 'The Mountain') has been a fan of chess ever since his dad taught him as a child. He’s played casually for years, and was even spotted getting a lesson on stream from world No. 2 Hikaru Nakamura. Honorable mentions go to Swedish footballer legend Zlatan Ibrahimović, NBA superstar Kobe Bryant and Canadian arm wrestler Devon Larratt.

Lewis Hamilton and Charles Leclerc were spotted enjoying an online chess during a live F1 event and attracted attention of newspapers, social media and show hosts 

And if you're not a sports fan and those names didn’t quite impress you—don’t worry. Let’s step back into the world of pop culture and music, where chess has quietly charmed some of music’s most iconic names.

Bob Dylan was often spotted with a chessboard during his Rolling Thunder Revue era, playing quietly behind the scenes while the world raged around him. There's even a rumour that Dylan’s manager once paid Bobby Fischer for a private match between the two. Chess terms even crept into his lyrics, with pawns, kings, and queens appearing in a few songs.

In the 1960s, Bob Dylan was a member of the chess-playing scene in Greenwich Village. Photo: Premier Chess.

It is said David Bowie played daily, sometimes on the beach, sometimes on film sets. He even taught his wife Iman how to play. He also owned a rare Man Ray-designed chess set from 1945, which later sold at auction for over $1.3 million, which makes us think he really liked chess.

David Bowie and Catherine Deneuve playing chess on the set of The Hunger, 1983

Sting called chess his mental warm-up on tour, something to keep his mind sharp before stepping on stage. a lifelong chess enthusiast who once described Garry Kasparov as “one of my heroes.” In 2000, he and four bandmates (ncluding Chris Botti and Dominic Miller) took on Kasparov in a simultaneous exhibition in Times Square. Sting lasted the longest, holding out for 45 moves before resigning.

 

One of the strongest players of all time posting about his fun with Sting on his X profile

Ray Charles, the legendary blind pianist and soul pioneer, was also a lifelong chess lover. He learned the game in 1965 and played by touch using a special tactile board. Chess gave him a mental challenge beyond music—and he even beat Willie Nelson three times in a row.

On the left: Ray Charles deep in a game of chess. On the right: his iconic sunglasses, chessboard, and other memorabilia on display at the Smithsonian’s National Museum of American History

Ennio Morricone, the Oscar-winning composer behind The Good, the Bad and the Ugly and Cinema Paradiso, was a devoted chess player throughout his life. He played daily and once said, “If I weren’t a composer, I would have been a chess player.” (Author’s note: thank God he didn’t!)

Morricone saw strong parallels between music and chess—structure, silence, and discipline. He even composed music for a 2004 event celebrating the 50th anniversary of the prestigious Linares Chess Tournament in Spain. For him, chess was more than a pastime—it was an art form in its own right.

Strongest woman player in history honoring Ennio Morricone on her X profile

Will Smith learned chess from his father and got so into the game that, after beating him, he trained with American grandmaster Maurice Ashley. Smith has credited chess with helping shape his mindset and approach to challenges. Keanu Reeves, known for his roles in The Matrix and John Wick, brings the same calm intensity to the board. Introduced to chess by a friend, he often plays in parks and cafés, enjoying the meditative focus it brings amidst Hollywood chaos.

Then there’s Woody Harrelson - part actor, part wildcard, full chess enthusiast. He’s played since age 11 and once pulled off a light-hearted draw against Garry Kasparov (with heavy help from GM Yasser Seirawan). At the 2018 World Chess Championship, Harrelson made the ceremonial first move for Caruana, but not before knocking over the King as a joke. “I thought it would be funny if I accidentally knocked over the king,” he later told reporters. “But then it turned out the joke's on me when I played d4”, Caruana had intended him to play e4. Watch the spectacle below!

We could go on and on! Honorable mentions in this category go to: John Wayne, James Dean, Stephen Fry and Stanley Kubrick.

Who knows which of these guys are any good and which just posed with a chessboard? But in the end, does it really matter? If chess offered them a sense of calm, a challenge, or simply a way to pass the time, that’s more than enough. 

We do know who isn’t very good. Bill Gates might be the richest person to ever play chess on camera, but his performance was… less than impressive. To be fair, he was up against the strongest player of our time: Magnus Carlsen. Still, the game lasted just 11 seconds. You can watch it below. And it wasn’t just the final blunder, signs of inexperience were clear by move three with the awkward Bd3.

In contrast checkout this photo of James Dean, the iconic 1950s actor known for Rebel Without a Cause, sitting alone with his little portable chess set, deep in thought, analysing a game. If that’s not the look of a serious chess player, I don’t know what is.

James Dean analysing a game, January 1992

There are surely many more who love chess but have never said so publicly. One of them might be Paul Rudd, who starred in an unforgettable short film about quantum chess alongside the awesome legendary physicist Stephen Hawking, created for Caltech (watch out for the Keanu Reeves cameo). The video is brilliant, hilarious, and surprisingly educational. We can only assume he doesn’t mind chess!

Liv Tyler never claimed to be a chess expert, but she seems ok playing against Magnus Carlsen in the image below! 

The two teamed up for G-Star RAW’s 2010 fashion campaign, which featured a promotional event called “The RAW World Chess Challenge” a match between Carlsen and the world, with Liv Tyler making the ceremonial first move.

G-Star Raw - making chess cool and fashion smart! 

We can sort of assume they became friends, as they reunited for a playful video set in New York’s Washington Square Park, where they posed as casual players hustling unsuspecting locals and passers-by. 

You might not know their name, but... maybe you should

They all played chess seriously when they were young. Not just weekend hobbyists, most were national champions, title-holders, or teen tournament winners.

But they didn’t become professional players. But - Chess, it turns out, gave them the edge they needed—not for checkmate, but for billion-dollar moves.

Strategic Thinking
Chess teaches you how to think ahead, weigh consequences, and manage risk. Peter Thiel, co-founder of PayPal and the first outside investor in Facebook, is a Life Master with a rating over 2200. He credits chess with helping him think several moves ahead, an essential skill in startups and investing.

Peter Thiel's USCF peak rating was 2342, which makes him a proper chess player!

Focus and Discipline
Success requires the ability to go deep and stay there. Demis Hassabis, a chess master at 13, built DeepMind and created AlphaZero, the AI that reshaped how we think about intelligence itself (the AI that stunned the chess world by teaching itself the game in hours and then defeating Stockfish, the world’s strongest engine at the time). That kind of breakthrough takes obsession-level focus—something every strong chess player understands.

Demis Hassabis's current rating is 2220, but here he making ceremonial fist move for the current world Champion Gukesh Dommaraju

Pattern Recognition
Seeing patterns quickly is key in both chess and business. Alan Trefler tied for first in the World Open at age 19, then left chess to start Pegasystems, a software company that now powers Fortune 500 giants. His chess background inspired the rule-based architecture that made it all work.

Logical Thinking
Chess helps train logical decision-making under pressure. Sergey Galitsky rose to Candidate Master level before turning to retail. He built Russia’s largest supermarket chain from scratch, applying the same cool-headed logic that wins on the board.

Creative Problem Solving
Chess isn’t just logic—it’s creativity under constraints. Joop van Oosterom, software Volmac billionaire and correspondence chess world champion, didn’t just play—he helped fund and shape the chess world behind the scenes.

Performance Under Pressure
Chess teaches you to stay calm, adapt fast, and thrive in high-stakes moments. Josh Waitzkin, the real-life prodigy behind Searching for Bobby Fischer, became an International Master before stepping away from the game. He later became a world champion in martial arts and now coaches elite performers. Waitzkin credits chess with training him to stay composed under pressure and pursue mastery in every field he enters. If you are a fan of Joe Rogan or not, checkout this inspirational chat with Josh. 

Josh Waitzkin FIDE rating is 2464 which probably makes him the strongest celebrity this article 

Why This Matters
Chess isn’t just for prodigies and professors. It can be the foundation for high-level decision-making in any field. These people didn’t just play well—they learned well. And when it was time, they moved on from the board to win at life.

Chess in Spotlight 

I bet when you started reading this article, you didn’t expect to hear about Arnold’s donkey or Liv Tyler hustling people in the park with the world No. 1. They say 600 million people worldwide know how to play chess, and around 100 million play regularly. It’s the most popular board game of all time and unlike many perks of modern life, it’s survived centuries and generations for a reason.

Chess is simple in its complexity. It’s an art, a sport, a way to pass time, a means to connect. You could say - pretty much everyone likes it so of course some celebrities do too, and we think that’s kind of awesome.

It’s funny how people might feel a bit embarrassed to binge a show, but proud to say they read books. In the same way, some hide their gaming habits, but feel proud to admit they play chess. Why is that?

Many famous people pose with a chess set, even if they barely know the rules. It shows up in ad campaigns unrelated to the game, in movie scenes to set a mood, even in everyday language - a strategic move, a pawn in the game, checkmate. Chess carries weight, even outside the board. Why is that?

Because chess isn’t just another game. It’s part of culture. It carries symbolism, values, and a kind of timeless cool. And somehow, it keeps bringing together legendary artists, musicians, actors, and billionaires alike.

References:

Celebrities and Chess
If Madonna likes chess, we like chess
Chess.com AS Interview
ChessBase – Schwarzenegger vs Tyson
Cape Town Chess – Arnold Classic Africa
Madonna vs. Julia Roberts and other matches
Why all Formula 1 drivers should play chess
These Famous Women Loved Chess Too
Julia Roberts, movie star and chess player
G-Star Raw makes playing chess cool again
Lewis Hamilton and Charles Leclerc reflect on chess cheating saga
Jack Whitehall reacts to what Lewis Hamilton & Charles Leclerc did
AFL star Jesse Hogan and his love of chess: ‘Within a month, I was stone-cold addicted’
The Five Most Unexpected Chess Players
RAW World Chess Challenge: Kasparov selects the World Team
Watch Stephen Hawking and Paul Rudd Face Off in a Game of Quantum Chess
ay-Z’s Chess Moves in Black Is King Are Actually Pretty Good
Ennio Morricone (1928-2020), Avid Chess Fan
Bob Dylan, The Avid Chess Player, Has Also Made Nobel Prize-Winning Music!
Man Ray Designs a Supremely Elegant, Geometric Chess Set in 1920–and It Now Gets Re-Issued
Interview: THE SYDNEY MORNING HERALD (2000)
Would You Play Chess Against Ray Charles?
Musical giants and chess
Chess NewsWill Smith talks about his young chess years
Top 5 Celebrities Who Play Chess (And Aren't Professional Players)
Is there any good chess player who quit chess and made a lot of wealth?
Chess and Famous Business Personalities