POKER LIFESTYLE

The Most Epic Celebrity Poker Moments of All Time

By Connor Whiteley
April 04, 2023

Poker is an attractive game for the rich and famous. Over the years, there have been plenty of celebrity appearances at large tournament series and televised cash games. Lucky for us, there are a ton of televised celebrity poker moments. Here are our top five epic celebrity poker moments of all time.

Celebrity poker

Celebrities Playing Poker: On the Small Screen

The early 2000s were the beginning stages of the Moneymaker poker boom. Players everywhere were learning how to play poker and entering the player pool, including many celebrities. The growing interest in the game led to multiple poker TV shows.

Most poker players have seen clips of High Stakes Poker, but around the same time, there was another poker show: Celebrity Poker Showdown. In this show, some of our favorite celebrities were pitted against each other in a Sit-and-Go No-Limit Texas Hold’em tournament for charity. The show featured some massive names like Don Cheadle, Bryan Cranston, Tony Hawk, Dennis Rodman, and many others. Today, you can catch Jennifer Tilly on shows like High Stakes Poker playing massive pots against top professionals.

Some celebrities are staples of poker tournament series as well. Each year at the World Series of Poker, celebrities come in droves. Brad Garrett is always in a few tournaments each summer, and you can catch his old co-star Ray Romano as well. Ben Affleck and Matt Damon have both played the WSOP Main Event a few times, too.

Athletes also find themselves in televised poker games. Paul Pierce had a PLO game on the popular Hustler Casino Live Stream. Retired New England Patriot Richard Seymour plays many WSOP tournaments, making it to Day 5 of the 2019 Main Event. Overseas, PokerStars has seen some soccer royalty play in Neymar and Cristiano Ronaldo. Other athletes associated with poker include Usain Bolt and Rafael Nadal.

Celebrities Playing Poker: Behind-The-Scenes

While plenty of artists and athletes have played in televised poker games, the Hollywood Hills and bustling streets of Manhattan are filled with high-stakes celebrity home games. Molly’s Game, the famed tale of Molly Bloom’s ventures as a home game runner in Los Angeles and New York, tells the story of some nosebleed home games among the country’s rich and famous. In LA, celebrities like Tobey Maguire, Ben Affleck, Leonardo DiCaprio, and others were said to have played. Over three years, Maguire’s poker earnings were an estimated $40 million. When the game moved to New York, rumors have it that Yankee All-Star Alex Rodriguez was the featured player at many games.

WATCH: Exclusive interview with Molly Bloom

Jennifer Tilly has mentioned in interviews that she has played in many L.A. home games where five and six-figure checks are passed around come settle-up day. With so much poker being played by celebrities, both on and off-screen, we have been lucky to witness some truly epic celebrity poker moments.

Top 5 Epic Celebrity Poker Moments

5. Kevin Hart Bluffs Daniel Negreanu

In the PokerStars Championship Cash Challenge, celebrities and poker pros faced off playing 150 hands of £25/£50 No-Limit Hold’em. Many big names were there, including poker legend Daniel Negreanu and comedy superstar Kevin Hart. Negreanu has always been known for his table talk, and Hart likes to make his tablemates laugh. While this was a relatively small pot, the talkative nature of Kevin Hart makes this hand amazing to watch.

In a three-way port, Hart let out an exclamation of joy on the 972 flop despite having JT off-suit. After the action checked through, Negreanu led small on the K turn and Kevin Hart quickly called. The ace of spades hit the river (completing the flopped flush draw). Daniel checks and Hart fires another very small bet. After Negreanu folded, Kevin slammed his hand face up and exclaimed “I bluffed Daniel” which led to a small round of applause from the tournament players in the event center.

You can see the hand below:

4. Matt Damon’s Oscar-Worthy Performance

Matt Damon is a great actor. He gave us the iconic Mike McDermott and many other wonderful on-screen characters. Despite his big screen accolades, Damon’s performance during a WSOP Main Event hand tipped the pros off.

After flopping a full house from the small blind in a four-way limped pot, Damon checked as did the other three players. On the turn, Matt Damon secured the winning hand as no other player could improve on the river. He checked again along with the first two players to act, then the final player bet just over half the pot. Damon, next to act, put on a charade, pretending as though he didn’t like the bet and doesn’t want to call. After a few seconds of this, he called, setting off alarm bells for the pros.

Damon fell into a recreational trap, overacting like he was weak which signified extreme strength to his seasoned opponents. Legendary WSOP commentator Lon McEachern even calls out Damon on his lackluster performance. The other two players folded and when Damon checked the river, his opponent quickly checked behind. Damon reveals the full house (to nobody’s surprise) and scoops the pot, remarking that he is surprised his opponent didn’t bet the river. While the play wasn’t spectacular, it is hilarious seeing the gifted actor perform himself out of some much-needed chips. At least Damon crushed his role in Rounders!

3. Brad Garrett has to Get Dinner

At the feature table during one of the many successful Ante Up for Africa charity poker tournaments, Brad Garrett makes an interesting decision for his entire stack. Alex Bolotin open-jammed his short stack with K-9 and got called by Mecs, holding T-T. Garrett next to act announced he has a very bad hand and tablemate Matt Damon offered some “coaching” by jokingly telling Brad to jam any hand, including 3-5 offsuit. Garrett then announced all in for not much more than the initial bet, said he has to go to dinner, then asked if he can take it back. Of course, he couldn’t and he showed 8-2 suited before launching into a comedy routine. His antics while sweating the runout and entertaining the crowd show just how epic having a comedian at the table can be.

2. Jennifer Tilly Plays Blind and SMASHES the Flop

In 2019, PokerGO held a televised cash game called Holidays with Hellmuth where Phil Hellmuth and other poker players faced off in a $100/$200 + $200 ante NL Holdem cash game. Jennifer Tilly, Hollywood star and longtime girlfriend of poker pro Phil Laak, was one of the participants in the cash game. While she was away from the table getting $20,000 in chips to add on, she was dealt KK and called the $400 straddle blind! Something I have seen (and regrettably done) in home games with my friends, but never expected to see happen in such a large game. Hellmuth called from the big blind with Q-5 and the straddler, James Bord checked his option holding T-8.

Amazingly, the flop is KT5, so everyone gets a piece but Tilly has a virtual lock on the hand. Hellmuth led for $900 and both players called. The turn 8 gave Bord two pairs, the last thing he wanted in this hand. Hellmuth checked, Bord overbet, sending $10,000 into a pot of only $4,200. Tilly then raised to $25,000 leaving herself only a few thousand behind and understandably Bord went all in drawing dead. Tilly of course called and won the pot.

While the postflop action itself isn’t super crazy (other than Bord’s huge overbet) watching a celebrity play her hand blind and walk into the flopped nuts is a great watch.

1. Miss Finland (Sara Chafak) Bluffs Ronnie Bardah

By far, this is the greatest celebrity vs. professional poker hand ever, and we are all lucky it was televised. On PokerStars’ Shark Cage, professionals and celebrities alike compete in a Sit-and-Go tournament with an interesting twist. On the river, when a player bets they also play a face-down card that reads “Bluff” or “Value”. If the bettor is bluffing and their opponent folds, that opponent is sent into a shark cage where they have to wait for a full rotation.

Sara Chafak, Miss Finland, limped from middle position with A-2 off-suit, and poker pro Ronnie Bardah checked his option with 8-4 off-suit from the big blind. The flop was Q54 with two spades, Ronnie bet 15k and Sara raised to 30k. After a call, the turn was another 4 giving Ronnie three of a kind. Ronnie checked and Sara fired for 55k, Ronnie check-raised to 155k, and miraculously Sara 3-bet to 255k (she loves the min-clicks). Ronnie called relatively quickly. When an off-suit 6 hit the river, Ronnie checked and Sara jammed over 700k and activated her “bluff” card. This sent Ronnie deep into the tank and he even exposed his cards trying to get a reaction out of the recreational Sara. To everyone’s disbelief, Ronnie folded and was sent into the shark tank after getting the bad news. The table erupted when they saw what Sara had just pulled off and to this day Ronnie still gets people bringing up the hand.

Check out the action here:

Best Celebrity Poker Players

We’ve discussed a lot of celebrities who play poker. From athletes to actors, there are plenty of stars who’ve been bitten by the poker bug. Some have developed into incredible poker players. Others may not have the skills to go up against the best, but they are incredible ambassadors of the game.

Best Celebrity Poker Players: Ambassadors

A great poker ambassador is someone who uses their personality and playing to strengthen the game and increase the player pool. These players can be world-renowned for their playing, like Daniel Negreanu, or passionate stars like my top three celebrity poker ambassadors below.

3. Kevin Hart

Kevin Hart brings his larger-than-life personality to the poker table whenever he plays. A constant source of entertainment, he attracts players to the table like moths to the flame. He has made some huge appearances, having worked in the past with PokerStars and partypoker on promotions, and even firing the 2017 $300k Super High Roller Bowl where he coolered Phil Hellmuth and Fedor Holz for their entire stacks. Hart is a wonderful ambassador for the game who truly enjoys playing poker and sticking all his chips in the middle even when he doesn’t have the correct pot odds to call.

2. Brad Garrett

Brad Garrett, as previously discussed, is great for poker. Whenever he shows up at the table he is gracious, funny, and inviting to all those around. He doesn’t shy away from attention and is constantly playing. Check out his HendonMob and you’ll see he doesn’t just show up for the big fields at the WSOP, but he grinds other tournaments around Vegas.

1. Norm Macdonald

Norm Macdonald was the epitome of a celebrity poker ambassador. He made an annual pilgrimage to Vegas during the WSOP, hosted a season of High Stakes Poker, and continuously promoted the game by doing poker interviews and making appearances at big tournaments. Unfortunately, Macdonald passed away in 2021 but he made a lasting impression on the poker world.

Best Celebrity Poker Players: The Sharks

Some celebrities have turned their love of poker into a lucrative hobby. These celebrities put their skills to the test and have come out on top, crushing private and public games.

3. Tobey Maguire

The only reason Tobey Maguire is not higher on the list is that his poker playing is almost exclusively behind the scenes. However, if the reports are true of his Hollywood home game escapades, he is dangerous at the poker table. Between Molly’s Game and some public court cases, Tobey Maguire’s poker earnings are astronomical, making him a celebrity poker shark.

2. Richard Seymour

The former Pro Bowl defensive end had an amazing career with the Patriots and Raiders, retiring after the 2012 season with three Super Bowl rings. Seymour has a different piece of jewelry on his radar now. He is a tournament grinder who has had some great success. With over $700k in earnings including a deep run in the 2019 WSOP Main Event and a third place finish at the 2018 PCA $25k high roller, it is clear Seymour’s tournament game is on point.

1. Jennifer Tilly

The clear number one, Tilly plays so many high-stakes poker games that it’s hard to consider her a celebrity who plays poker; she feels more like a poker player who is also an actor. Tilly has made appearances on countless shows like Poker Night in America, High Stakes Poker, The Big Game, and Poker After Dark and has been successful in all of them. Streamed games aside, Tilly also has WSOP success. She won the 2005 $1,000 NL Holdem Ladies event for a WSOP bracelet. That is a feat few poker players earn, even professionals. As a celebrity player and ambassador, it doesn’t get better than Jennifer Tilly.

Poker is an incredible game, so it is no wonder celebrities are attracted to the tough decisions, big bluffs, and mega coolers. As poker content continues to grow, we will continue to get epic celebrity poker moments. Although I doubt we’ll ever see a bigger bluff than Sara Chafak’s, I would love to see Tilly or Hart give it a shot.

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Connor Whiteley poker author
Written By.

Connor Whiteley

Connor Whiteley is a financial services professional and freelance writer who spends as much time as possible on the felt. Previously, Connor was a dealer in various underground Los Angeles poker games, but left the city and those games to raise his daughter with his loving wife Jennifer. Connor is constantly staying up to date […]

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