Famous Actors Who Love to Test Their Luck



If you take away their giant piles of cash, collections of cars, private jets, designer suits, and manors that could easily house twenty families, celebrities are, in many ways, just regular people. They are not immune to the thrills of betting on sports, trying their luck on slot machines, or going head-to-head with the dealer at the poker table. While some have managed to find their hidden talents, others have lost huge chunks of their wealth.

Here are some famous actors and their off-screen mishaps.

Pamela Anderson


We’ll start things off with one of the most recognizable film and TV names of the ‘90s, Pamela Anderson. She rose to fame thanks to her role in Baywatch, where she played a beautiful slow-motion lifeguard who saved people from drowning. Over the years, she has starred in some low-budget TV shows and movies (shout out to the beautiful trash that is 1996’s Barb Wire) and appeared as Borat’s love interest in the 2006 mockumentary.

While some might call her general acting skills a bluff, she definitely uses that to her advantage at the poker table. She’s been an avid gambler for years, and this addiction has even affected her romantic life. Apparently, in order to settle a poker debt of $250,000, she agreed to make out with her long-time friend and professional poker player Rick Salomon, which eventually led to the pair getting married in Las Vegas. The marriage fell apart in a matter of weeks, but Pamela’s love for casino games has remained as strong as before.

Charlie Sheen


If you were to bump into Charlie Sheen and confront him about his gambling problem, he would laugh it off with a cigar in his mouth, with two ladies of the night on each arm. Sure, gambling might not be the first on his list of problems, but it’s definitely up there.

Many of his misfortunes with sports betting came to light during his divorce trial with Denise Richards. One of the reasons she filed for divorce in the first place was that he was reportedly betting about $200,000 every week. She mentioned a sad anecdote where, while he was driving her to the hospital to give birth to their second child, he stopped for a moment to place a bet over the phone.

His enthusiasm for betting has died down over the years, perhaps culminating at a Manny Pacquiao boxing match where he bet an entire million. Apparently he had a dream that he would win and, after he did, he felt indifferent. For a man who is all about life’s thrills, this was naturally devastating.

Tobey Maguire


Tobey Maguire is much more than a casual poker player. In 2004, he began playing various tournaments and got poker tips from professional player Daniel Negreanu. He even tried his luck in the World Series of Poker for a couple of years in a row. Although he never discussed amounts, sources say that he was quite successful.

In recent years, Tobey Maguire has been getting some really bad publicity on account of his arrogant behavior connected with his gambling habit. Apparently the ex-webslinger participated in exclusive high-stakes poker games with other celebrities and managed to be the biggest douchebag in the room.

The organizer of these games, Molly Bloom, recounted an instance where Maguire demanded that she barked like a seal to earn her tip of $1,000. The best supporting actor in Wonder Boys was reportedly agitated and wanted to humiliate her before eventually taking over the game. Despite that, according to Molly, he had already won millions of dollars up to that point.

Ben Affleck


Another star who participated in Molly’s Game was Hollywood A-lister Ben Affleck. There have been numerous rumors and speculations about his gambling addiction, but he has denied them every time. Looking at the facts, it’s clear why he would rather see himself as a professional and not an addict. But then again, who wouldn’t?

Besides winning the California State Poker Championship in 2004, he hasn’t had that much luck with poker. He lost around $400,000 to US talent agent Ron Meyer and hasn’t really won anything big since. On the other hand, he was so good at blackjack (winning nearly a million in just two trips) that he was asked to stop playing at the Hard Rock Hotel. They thought he was pulling a Rain Man stunt on them.

His gambling is so well-known that many newspapers thought it led to his divorce with his Daredevil co-star Jennifer Garner. It turns out they were completely wrong. It had nothing to do with his gambling. Heavy drinking and infidelity, sure. But not gambling.

Ashton Kutcher


Charlie Sheen and the actor who replaced him on Two and a Half Men, Ashton Kutcher, have something in common: They both place bets on sports. But while Sheen did it for the sheer thrill of the game, Kutcher saw sports betting as an investment opportunity. He does numerous calculations, pulls out a ton of data, and makes the safest bets possible. While there is some risk involved, it’s far from reckless.

The actor who played Kelso in That ‘70s Show is rumored to have been placing bets from one of the biggest betting syndicates in the United States, headed by Billy Walters. He probably learned a lot from the experience and decided to use his knowledge to his advantage. Recently, he has been investing in Unikrn, a betting company that focuses on esports and video games. He believes betting on video games is the next big thing.

Jennifer Tilly


You probably know Jennifer Tilly as Tiffany Valentine, the murderous doll from the Child’s Play film series. But she’s not just an actress; she also moonlights as a professional poker player. Her live tournament winnings amount to a total of nearly $1 million.

A big part of her motivation was her father, who introduced her to the world of gambling through a World Series of Poker video game. When she moved to Hollywood, she learned the real game from her boyfriend, and the rest is history. In 2015, she won the World Series of Poker with slightly over $150,000.

Other Celebrities

Of course, actors and actresses aren’t the only people who like to gamble. There are plenty of other celebrities who can’t resist the urge to test their luck and try to win big. If you’re curious to see who else has a betting hobby, make sure you check out this list.

Comments are closed.