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The Worst Celebrity Poker Players In Hollywood

by Houston Curtis |  Published: Oct 07, 2020

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In my last article I gave you a detailed rundown of the top five celebrity poker players I have played with over the years in high-stakes, private poker games. This issue I’m going to flip the script to talk about the top five worst celebrity poker players I’ve ever played with!

As I mentioned in my previous article, a celebrity doesn’t have to be an actor, rock star, or sporting idol, as Tinseltown also celebrates the movie mogul producers, tabloid headline makers, run-amok trust fund types, billionaires, captains of industry, and frankly, anyone who spends time dodging paparazzi, posting viral selfies from their private jet or is escorted straight up the elevator to Soho House shirtless and barefoot.

My primary criteria for this list are that I have had to have played with these players in a private, VIP invite-only, cash game setting. While I’ve played in tournaments with many celebs who have gone broke before Phil Hellmuth even showed up to play his first hand, it would be unfair to make such a judgement call without having spent some serious hours together at the table in an environment where the celebs feel they are amongst their peers.

No. 5 — Kevin Hart

Let me preface this choice by saying that despite being on my list, Kevin Hart already had a couple decent tournament cashes under his belt before he ever began playing in serious high-stakes, LA-based cash games, and even before he became the highest paid stand up comedian in the world. In 2008 he managed a second-place finish at the Bicycle Club during Mo’s Deep Stack no-limit hold’em event with an impressive $16,330 win. And he even came in first at Larry Flynt’s Challenge Cup in 2010 (probably near the time I started playing with him) where he won a respectable $20,265.

So, then why is Kevin on this list? I played with him on more than one occasion in a particularly shady, private LA home game that reminded me of the sketchy games I had rounded back in the late 90’s. He was funny as hell, but at that point was still playing cash game poker like a tournament player. Pushing all in preflop off a three-bet with A-K to of course wake up to pocket aces drawing damn near stone dead. To be fair, I’ve heard Kevin’s game has improved over the years. For me, it was just fun to listen to him crack jokes at the table while donking off 30 or 40 grand. It was a two-for-one special whenever Kevin played… we got paid and entertained in the same night!

No. 4 — Guy Oseary

At the age of 19, Guy Oseary joined Madonna’s record label and immediately became known as her golden boy, rising through the ranks all the way from being an A&R rep to becoming chairman. Oseary became a legend in Hollywood by developing a roster of artists that included The Prodigy, Alanis Morissette, Deftones, The Wreckers, Paul Oakenfold, Michelle Branch, Summercamp, and soundtracks on such film series as Austin Powers, The Matrix, and Kill Bill. Oseary guided Maverick to sell over 100 million albums worldwide and secured its spot as one of the industry’s leading boutique record labels.

I first met Guy back when our game was still happening in Tobey Maguire’s kitchen in the Hollywood Hills. I’ve never felt one way or another about meeting your run of the mill A-list actor, but I have to admit, I was really excited about meeting Guy. By the age of 19 he had a career most people would sell their soul for and by 25 he had more money than he could ever possibly spend. If you would have bet me on whether or not Guy Oseary would know his way around a poker table, I would have bet big money that the kid could play… and I would have lost!

Out of the gate, Guy had a very nervous energy about himself. I figured it was just his personality. I mean, what does this kid have to be nervous about? But it barely took one orbit before I realized that aside from knowing the basic rank of hands, Guy had absolutely no understanding of the game. He had no “card sense,” which really surprised me.

I wrote about a hand I had with him in my book, Billion Dollar Hollywood Heist, where the cards are dealt, a few guys limp in, and then Guy looks at his hand, and literally jumped out of his seat, with his eyes as wide and excited as possible, yelling, “I’m all-in!” I started cracking up as everyone around the table began to fold. Then I looked down at the one hand I did NOT want to see, one of two hands that I refuse to lay down preflop no matter how much money is on the line. Pocket kings! After seeing the kings, I said something to the extent of, “Guy, it’s your lucky day.”

I then called with K-K and of course, Guy turned over A-A. There was a king right in the window, however, and I out-flopped him, busting him for everything he had. I honestly don’t think he realized he had lost the hand until the money was being pushed my way and I was apologizing to him for the bad beat. To this day, I’ve never seen anyone telegraph aces that blatantly! How cool would I have looked if I just laid down the kings?

No. 3 — David Schwimmer

David Schwimmer played the lovable, but always anxiety-ridden Ross from the hit TV show Friends. He had played poker regularly in a game that I went to occasionally held by Oscar-winning producer Jon Landau, who was famous for huge projects like Titanic and Avatar.

It was hard to tell if Schwimmer was just a bad player, or if he was really sweating a thousand-dollar call after making a million dollars per episode and having more money than he’ll ever be able to spend. But sure enough, every time I played with the guy he would agonize over every decision as if he was about to call with his rent money. Annie Duke told me he got so rattled playing one night when she was a guest of the game that he had to leave early because the anxiety was just too much.

You know, good old Ross from Friends is funny to watch on reruns, but he’s just like that in real life! And in real life, it’s not funny, it’s annoying.

No. 2 — Joe Francis

In the early 2000’s, Girls Gone Wild creator Joe Francis was probably more famous among young Hollywood celebrities than anyone else. During his hey-day he ran with the likes of Paris Hilton, Kim Kardashian, Lindsay Lohan, and others in the Hollywood party crowd. Joe would love spinning tales about his private jets, and mansions, and all the money he had made.

I had known Joe long before we ever started playing high-stakes poker together due to the fact that I was the creator of The Best of Backyard Wrestling, which sold via late night infomercial spots at the same time he was selling Girls Gone Wild. Always an over the top character, when I first met Joe, he literally threatened to sue me while simultaneously trying to do a contract with me, all within the same half hour meeting.

Needless to say, Joe’s “luck” in business did not translate at all to poker. You got to love playing for hundreds of thousands of dollars with a guy who doesn’t even know the rank of hands. (Damn that was a good game!)

I remember one night, Joe had flopped a set of aces against Bob Safi. But Joe just kept checking and Bobby would check after him to peel off a free card. By the river the board was showing the nuts with Q-J-10-K-A rainbow (meaning the nuts were on board) and Bobby moved all in. Joe looked at the board confused and went into the tank forever until he finally raised his hand like a schoolboy and said, “I have a question about the rules.”

To which Bobby shouted, “You can’t ask a fucking question about the rules of poker while you’re in the middle of the fucking hand you damn idiot!” To which Joe replied, “Idiot? I bought my first jet when I was 23 and my second jet when I was 24!” which was met with an uproar of laughter and embarrassment all rolled into one. He literally didn’t know that he could play the board and was calling into a chopped pot.

No. 1 — Matt Damon

At this point, many of you are probably heartbroken just reading Matt’s name in the top slot. Well, let me ease the pain at least a little bit. Do I really think Matt is worse than all of the other players mentioned on this list? Nah. In fact, he probably deserves to go in the no. 5 spot instead of no. 1, but who wants a top five countdown that ends on the Girls Gone Wild guy?

I’m afraid we have to hand this honor to Matt Damon simply because he is not only a huge A-list celebrity, but because he’s Mike McDermont! He’s Mikey D from Rounders, arguably the greatest poker movie ever made! Plus, Matt is a highly skilled actor. One of the best in the business today. And aren’t actors supposed to make great poker players? Well… not always!

The night Matt Damon played in our game we had a ton of laughs, shared some fun stories and at the end of the night, Matt’s buddy Ben Affleck was cutting me a check for $45,000 to cover Matt’s loss because Matt didn’t bring his check book. Unfortunately, Matt Damon’s acting skills as a great poker player are just that. Acting! Because Matt doesn’t really have a feel for the game, and certainly doesn’t take it seriously like Ben. My guess is, if Matt really wanted to play, he could learn the game. But until I have the chance to play with him again, I’m guessing that the Mike McDermott character he so brilliantly portrayed in Rounders will never show back again. That is, unless we get lucky enough for him to reprise his role in Rounders 2!

So there you have it. The top five worst celebrity poker players I’ve played with over the years. If you haven’t had the chance to read my book, I actually share stories in more detail about each and every one of these players in Billion Dollar Hollywood Heist. If you would like an autographed copy, I am NOW SHIPPING them! Just go to my website kardsharp.com to purchase the limited-edition copy before they’re all gone.

And remember, Stay Sharp! Stay Kardsharp! ♠

Houston Curtis Houston Curtis, founder of KardSharp.com and author of Billion Dollar Hollywood Heist has lived a successful double life as both a producer and card mechanic for nearly 30 years. His credits include executive producing gambling related TV shows such as The Ultimate Blackjack Tour on CBS, The Aruba Poker Classic on GSN and pioneering the poker instructional DVD genre with titles featuring poker champion Phil Hellmuth.

Barred for life from Las Vegas Golden Nugget for “excessive winning” at blackjack, Houston is one of the world’s most successful card mechanics and sleight-of-hand artists of the modern era. Curtis, who rarely plays in tournaments, won a 2004 Legends of Poker no-limit hold’em championship event besting Scotty Nguyen heads-up at the final table before going on to co-found the elite Hollywood poker ring that inspired Aaron Sorkin’s Academy Award-nominated film Molly’s Game.

Curtis resides in Phoenix, Arizona where in addition to running a production company and independent record label, he is also a private gaming/casino protection consultant to clients across the globe seeking insight into master level card cheating tactics via advanced sleight-of-hand technique. To reach Houston for a speaking engagement, consulting or production services send email to stacked@Kardsharp.com.

All views expressed in this article are those of the author and do not necessarily reflect the views and opinions of Card Player.