Celebrities Playing Chess — Checkmate!

Checkmate Awaits!
Famous Faces at the Chessboard
Celebrating National Chess Day!

Published October 11, 2025 7:00 AM PDT

Attention all kings and queens! It’s National Chess Day, and we’re celebrating with a special showcase of celebrities caught in action playing chess!

Chess is the perfect game for all occasions, whether you’re chilling with Jake Paul or Kelly Bensimon!

Chess is also an ideal choice for those cozy days indoors with delightful company, such as Amy Schumer!

And if boredom hits while vacationing, don’t forget the chessboard! Sparring with someone like Winnie Harlow can turn the game into an unforgettable time!

Amy Schumer


Jake Paul


Kelly Bensimon


Winnie Harlow

wbq.push(function gdprConnatix() {
var response = ‘unknown’;
function accept() {
if (response === ‘accepted’) {
return;
}
(function () {
if (typeof window.cnxps !== ‘undefined’) {
return;
}
window.cnxps = {};
window.cnxps.cmd = [];
!function (n) {
var t = n.createElement(‘iframe’);
t.src = “https://www.tmz.com/2025/10/11/celebrities-playing-chess-checkmate/javascript:false”;
t.display = ‘none’;
t.onload = function () {
var n = t.contentWindow.document;
var c = n.createElement(‘script’);
c.src = ‘//cd.connatix.com/connatix.playspace.js’;
c.setAttribute(‘async’, ‘1’);
c.setAttribute(‘type’, ‘text/javascript’);
n.body.appendChild(c);
};
n.head.appendChild(t);
}(document);
})();
response = ‘accepted’;
}
function reject() {
if (response === ‘rejected’) {
return;
}
response = ‘rejected’;
}
watchConsent(function(canUse) {
canUse(‘connatix’) ? accept() : reject();
});
});

window.wbq = window.wbq || [];
window.wbq.push(function loadOutbrainSmartfeed(app = window.TMZ) {
const outbrainDiv = document.getElementById(‘outbrain-permalink’);
const page = app.select(app.selectors.getPage);
if (!page?.url) {
outbrainDiv.parentNode.removeChild(outbrainDiv);
return;
}
if (window.DEVICE_VIEW === ‘smartphone’) {
outbrainDiv.style.backgroundColor = ‘white’;
outbrainDiv.style.display = ‘flex’;
}
const smartfeedDiv = document.createElement(‘div’);
smartfeedDiv.setAttribute(‘data-widget-id’, ‘AR_1’);
smartfeedDiv.setAttribute(‘data-src’, page.url);
smartfeedDiv.className = ‘OUTBRAIN’;
const script = document.createElement(‘script’);
script.type = ‘text/javascript’;
script.setAttribute(‘async’, ‘async’);
script.src = ‘https://widgets.outbrain.com/outbrain.js’;
outbrainDiv.appendChild(smartfeedDiv);
outbrainDiv.appendChild(script);
});