Celebrities Who Play Chess
From Humphrey Bogart hustling chess in New York parks to RZA on the cover of Chess Life magazine, famous chess lovers prove this game is truly for everyone.
Published 2026-02-01 | Last verified 2026-02-14
Professor Archer says: People are always surprised when they learn how many famous actors, musicians, and athletes play chess. But I am never surprised. When I learned that Humphrey Bogart used to hustle chess in New York parks before he became famous, or that RZA plays three hours of chess every day, it confirmed what I have always known: chess attracts curious, driven people. That describes every successful person I have ever met. And it describes you, too, for being here.
Hip-Hop and Chess: RZA, GZA, and the Wu-Tang Connection
No discussion of celebrity chess can begin without the Wu-Tang Clan. RZA learned chess at age eleven and now plays an average of three hours a day. He was featured on the cover of Chess Life magazine in January 2021, and he won the Hip-Hop Chess Federation's first annual tournament. Chess imagery saturates Wu-Tang's music, from the 1993 track "Da Mystery of Chessboxin'" to GZA's platinum-selling Liquid Swords album artwork.
GZA released a chess-themed album with DJ Muggs called Grandmasters in 2005, where every track has a chess title - Queen's Gambit, Destruction of a Guard, Unprotected Pieces. He learned the game in 1975 and rediscovered it playing with other Wu-Tang members in 1992. RZA has also trained with chess prodigy Josh Waitzkin (the real-life subject of Searching for Bobby Fischer) through the Hip-Hop Chess Federation, an organization that fuses music, chess, and martial arts to promote strategy and non-violence.
Jay-Z learned chess from his father and wrote in his autobiography Decoded that his father taught him life was like a chessboard where you had to think several moves ahead. He has called himself the Bobby Fischer of rap in his lyrics. Beyond hip-hop, Bono from U2 learned chess during the famous 1972 Fischer-Spassky match, became chess champion of his school, and once considered becoming a professional chess player before music took over.
Ray Charles, Sting, and Musicians at the Board
Ray Charles learned chess in 1965 during a rehabilitation program near Los Angeles, where his doctor taught him the game. Blind since age seven, Charles used a specially designed board where black squares are raised, white squares are lowered, and pieces are distinguished by touch - pointed tops for black, flat tops for white. He would run both hands over the board after every opponent move to feel the new position.
Charles played regularly with Willie Nelson, who later joked about their games in the dark. When Charles lost to former US Champion GM Larry Evans in 2002, Evans complimented him for spotting a tactical trap. Charles replied with characteristic humor. His chess set was donated to the Smithsonian Institution after his death.
Sting keeps a giant chessboard on the grounds of his estate in France. In 2000, he played an exhibition game against Garry Kasparov in Times Square alongside four bandmates - Kasparov defeated all five simultaneously. Sting has called Kasparov one of his heroes. Madonna, meanwhile, was tutored by Scottish chess champion Alan Norris and reportedly played approximately 19,000 games on the Internet Chess Club, reaching a personal best rating of around 2003 - strong club player territory.
Humphrey Bogart: Hollywood's Strongest Chess Player
Before he became one of the greatest actors in film history, Humphrey Bogart hustled chess players for dimes and quarters in New York parks and at Coney Island. At one arcade, he sat in a window playing all comers for a dollar a game, typically facing about forty people a day.
Bogart was estimated to play at near-master strength. In 1955, he achieved a draw against GM Samuel Reshevsky in a simultaneous exhibition at Beverly Hills. In 1952, he played GM George Koltanowski, who was playing blindfolded - Koltanowski still won, but the fact that Bogart lasted forty-one moves against a blindfolded grandmaster speaks to his ability. He served as a USCF tournament director, was active in the California State Chess Association, and helped sponsor the 1945 Pan-American Chess Congress in Los Angeles.
Bogart played chess every day between takes while filming. When asked in a 1945 interview what things mattered most to him in life, he listed chess among them. When he passed away, a chessboard sat beside his bed.
Will Smith, Woody Harrelson, and Arnold Schwarzenegger
Will Smith learned chess from his father at age seven. His wife Jada Pinkett-Smith once arranged a Valentine's Day surprise: a three-hour chess session with Grandmaster Maurice Ashley, one of the first Black grandmasters. Smith became so engrossed that Ashley later warned others to be careful playing him. Smith wrote the foreword to Ashley's book Chess for Success and has shared stories about how chess taught him lessons about the arrogance of overconfidence.
Woody Harrelson started playing at age eleven and holds an estimated rating of around 1580. In 1999, he played a consultation game against Garry Kasparov in Prague, aided by GM Yasser Seirawan from the audience - the game ended in a draw. Harrelson made the ceremonial first move at the World Chess Championship in both 2016 and 2018. At the 2018 Carlsen-Caruana match, he fumbled the first move on camera, accidentally knocking over Caruana's king before getting it right on his third attempt. He has also visited the chess club at HMP Wormwood Scrubs prison in England to play matches with inmates.
Arnold Schwarzenegger started playing chess at age eight with his father in Austria. He continued playing at the gym after moving to America and reportedly drew Garry Kasparov in a 2002 exhibition game. His Arnold Classic sports competition series features chess as one of its official events. During COVID-19, he promoted chess in stay-at-home videos alongside his miniature donkey Lulu, posting that she was not the best chess partner but she was getting there.
Athletes on the Chessboard: Lennox Lewis, Jaylen Brown, and the NBA Chess Club
Three-time world heavyweight boxing champion Lennox Lewis plays chess four times a day and has logged over 5,200 games on Chess.com. He has drawn explicit parallels between the ring and the board, noting that both are about advancing while keeping yourself well defended. His former trainer Emanuel Steward once worried that Lewis was overthinking in the ring because he was applying chess-like strategic analysis during bouts. Lewis funded an after-school chess program for disadvantaged youths, and one participant earned a university chess scholarship.
The NBA has developed an informal chess culture. 2024 Finals MVP Jaylen Brown was captain of his middle-school chess team, taught by his grandfather. Two days before the 2016 NBA Draft, Brown faced nine-year-old national champion Nico Chasin at the Marshall Chess Club - and lost. He calls the knight his favorite piece because of its craftiness. Former NFL lineman John Urschel, who retired at twenty-six to pursue a PhD in mathematics at MIT, holds a USCF rating of 1764 and has competed in rated tournaments.
Former NBA MVP Derrick Rose picked up chess for cognitive health benefits and has collaborated with Magnus Carlsen's Freestyle Chess organization. Other NBA players known to play include Giannis Antetokounmpo, Luka Doncic, Victor Wembanyama, and Gordon Hayward.
Tech Leaders: Bill Gates, Peter Thiel, and Richard Branson
The most famous celebrity chess moment in recent memory belongs to Bill Gates. In January 2014, on the Norwegian-Swedish talk show Skavlan, Gates played World Champion Magnus Carlsen with two minutes on his clock versus Carlsen's thirty seconds. Carlsen checkmated Gates in just nine moves, using only twelve seconds of his time. The game was nicknamed "I'm Just a Bill" on chessgames.com.
PayPal co-founder Peter Thiel is the strongest chess player among prominent tech figures, holding the title of USCF National Master with a peak rating of 2342 - stronger than over ninety-nine percent of all rated players. His FIDE rating reached 2199, one point short of the Candidate Master title. He once finished ahead of GM Hikaru Nakamura in a tournament and held a draw against GM Gregory Kaidanov. He integrates chess concepts into his Stanford University lectures.
Richard Branson has called chess the best game in the world and claims to have played thousands of games. He keeps a giant chessboard at his estate and has played against tennis legend Bjorn Borg on Necker Island. Howard Stern studied with National Master Dan Heisman for approximately four years, improving from a 900 online rating to over 1700 - a well-documented case study in adult chess improvement published by US Chess.
What Celebrity Chess Players Teach Us
The range of skill among celebrity chess players is enormous. Peter Thiel plays at National Master level. Humphrey Bogart could hold his own against grandmasters. Woody Harrelson drew Kasparov with help. Bill Gates lasted nine moves against Carlsen. Every one of them found value in the game, regardless of their rating.
These public figures demonstrate that chess appeals to people from every walk of life and every level of ability. Actors, athletes, musicians, entrepreneurs, and scientists all find something worthwhile on the sixty-four squares. Most celebrity chess players are casual to intermediate. They play for the mental challenge, the social connections, and the genuine enjoyment - exactly the same reasons that millions of people play.
If someone managing a film career, a championship boxing schedule, or a billion-dollar tech company can find time for chess, you can find fifteen minutes for a game. The benefits are available to everyone.
Questions About Celebrity Chess
Who is the strongest celebrity chess player?
Peter Thiel, co-founder of PayPal, holds the title of USCF National Master with a peak rating of 2342, making him significantly stronger than any other well-known celebrity player. Among historical celebrities, Humphrey Bogart was estimated to play at near-master strength and once drew GM Samuel Reshevsky.
Are celebrity chess players actually good at chess?
Skill levels vary enormously. Peter Thiel is a National Master. Madonna reportedly reached a 2003 rating on the Internet Chess Club. Woody Harrelson plays at around 1580. Howard Stern trained to reach 1700. Others like Bill Gates play casually. The point is not the rating - it is that they all find value in the game.
Why do so many rappers and hip-hop artists play chess?
Chess resonates with hip-hop culture because both value strategic thinking, competition, and rising through adversity. RZA and the Wu-Tang Clan brought chess into hip-hop consciousness through their lyrics, album art, and the Hip-Hop Chess Federation. Jay-Z described chess as a metaphor taught to him by his father for thinking ahead in life.
Has any celebrity ever beaten a grandmaster?
Woody Harrelson drew Garry Kasparov in a 1999 consultation game in Prague, though he had help from GM Yasser Seirawan. Humphrey Bogart drew GM Samuel Reshevsky in a simultaneous exhibition. Arnold Schwarzenegger reportedly drew Kasparov in 2002. These were informal settings, but they are real achievements.
Can chess actually help with performance in other areas?
Many celebrity players report that chess improved their decision-making and composure. Lennox Lewis credited chess with sharpening his boxing strategy. Will Smith described chess as teaching him about overconfidence. GM Maurice Ashley taught Smith visualization techniques that Smith later applied to setting life goals.
Professor Archer says: The celebrities who play chess are not special because they are famous. They are special because they chose to keep learning, to stay curious, and to embrace a challenge that has no finish line. Woody Harrelson drew Kasparov. Ray Charles played chess in the dark. Bill Gates sat across from Carlsen and lasted nine moves. You can make the same choice they did. You do not need fame - you just need a board and the willingness to begin.
Quick Quiz
Which celebrity is a USCF National Master with a peak rating of 2342?
- Bill Gates - Bill Gates is an enthusiastic casual player but was famously checkmated by Magnus Carlsen in just nine moves on the TV show Skavlan.
- Peter Thiel (Correct) - Correct! PayPal co-founder Peter Thiel holds the title of USCF National Master with a peak rating of 2342, making him stronger than over 99% of rated chess players.
- Woody Harrelson - Woody Harrelson is a dedicated chess player at around 1580 rating. He drew Kasparov in a consultation game with help from GM Yasser Seirawan, but he is not a National Master.
- Humphrey Bogart - Humphrey Bogart was an excellent player estimated at near-master strength who drew GM Reshevsky, but the National Master title with a 2342 peak rating belongs to Peter Thiel.