Matt Damon and his Gambling Passion: Biggest Win and Losses

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 Matt Damon, the award-winning American actor, film producer, and screenwriter, has featured in movies like The Departed, The Martian, Jason Bourne, and Good Will Hunting among others.  He has bagged several awards like the Best Original Screenplay for Good Will Hunting produced in 1998, Best Supporting Actor for his role in Invictus, and Best Actor in The Martian.

Alongside his long acting career, Damon is one of the famous gambling celebrities, adding to the long list of other gambling movie stars like Ben Affleck, Leonardo Di Caprio, and Sean Connery. His passion for gambling is said to have been inspired by his most recent film, Rounders, which is credited for igniting the 1998 poker boom. He is said to have developed a strong interest in poker while doing research for his role in the film – being a sexy thriller that talks about underground high stakes poker.

In the movie Rounders, Damon plays the main character Mike McDermott, a law student with outstanding talent and skills as a poker player. Despite his talent for playing poker, the student vows to quit gambling after losing his money to a Russian mobster. His however finds himself at the gambling tables when his old friend is released from prison to help clear his friend’s debt.

Poker against the Best

Away from the movie role, Damon is said to have spent a considerable amount of time in some of the sites honing his gambling skills as a poker player. He could occasionally show up at various poker tournaments throughout the course of his acting career. Players who want to perfect their pokers skills can try their hand at a no wagering casino in Canada while passing time online so they can eventually play for real money. To give his passion for poker a real go at the best casinos, Damon joined the 1998 World Series of Poker (WSOP) while still researching for his role in Rounder. He lost $25k to retired American poker player and two-time World Series of Poker Main Event champion Doyle Brunson in what was potentially one of his substantial losses in gambling.

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In 2010, the actor made it to the WSOP main event, which attracted sitcom star Ray Romano and fellow Oscar winner and close friend Ben Affleck. He lost again in an event that attracted a large audience and was won by Canadian Jonathan Duhamel, who bagged the $9 million prize.

One for Charity

His love for gambling saw him join the 2009 Ante Up for Africa event, a poker tournament that brings together the who is who in the celebrity world from across the globe. The tournament is known for donating all proceeds to charity. In the 2009 event, Damon joined 137 other celebrities and managed to play as far as 35 players to go. He finally quit the competition that was won by Alex Bolotin from Belarus, who went home with $177,730 winnings and donated half the amount to charity.  

At the time, Damon would have wanted to amass a few pennies for his charity projects including Not on Our Watch Project aimed at preventing mass atrocities in war tone areas like Darfur, and which he co-founded with Brad Pitt, George Clooney, David Pressman, Don Cheadle, and Jerry Weintraub.

Other Gambling Celebrities in Canada

While gambling may not traditionally be a Canadian culture, recent years have witnessed a poker craze going wild motivated by the government’s friendly regulations and welcoming attitude towards gaming. Various actors in the casino industry from around the world are also setting up shops in Canada offering a variety of games and gambling opportunities. Although Canada’s casino marketing is ripe and booming, the several wagering requirements sometimes discourage would-be players from participating. Below is a detailed review of the top casinos in Canada which you can find online. Online gambling in Canada has attracted several big-time movie stars and artists who are either supporters of the game or are active gamblers.   

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Pamela Anderson

The Canadian-American star is known for her iconic hit TV show Baywatch and while the 53-year old may have many hobbies and eccentricities, she is also an avid online gambler. Pamela has promoted multiple online gambling brands like Bally Gaming and Systems and even played for $250,000 prizes at Las Vegas casinos, making her one of the biggest gamblers in Vegas. She owns a Baywatch online casino game and in 2005, she launched the Pamela Anderson Playboy line of slots and the Palms Casino Resort in Las Vegas, Nevada.


Regarded as a pioneer of dub, trap, and EDM music and one of the most successful electronic music artists in modern history, Deadmau5 has on several occasions shared his love and support for professional casino gambling.  His love for gambling inspired the launch of the EDM-themed online slot game named Deadmau5.

Justin Bieber

Justin Bieber is one of Canada’s most successful music icons with more record sales and Billboard No.1s than any other Canadian artist alive today.  In addition to his solid music career, Bieber is also an actor and has featured in several films including Behaving Badly and Zoolander 2.

Aside from his music and acting careers, he is a penchant for gambling, especially poker and blackjack. He is known for high-stakes casino card games and is a frequenter of some of the ritziest poker lounges in Las Vegas, Atlantic City, and London.


Drake is an avid partier and known for splashing large sums of money on poker, roulette, and blackjack. He is on record for gambling more than $200,000 in a single sitting at the Hard Rock Casino in Atlantic City.

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Top No Wagering Casino Canada


Launched in 2017, PlayOJO offers an excellent gambling experience with impressive bonuses and no wagering conditions. Members have access to more than 3,000 different games to play and gamble. In addition, the PlayOJO games catalog also includes more than 200 card and table games. Players get a bonus of up to 50 spins on their first deposit and all wins made on these spins belong to the player.

888 Casino

888 Casino was launched in1997 and currently boasts of more than 70 million users. The casino is known for high-quality jackpot slots with top-notch security. 888 Casino offers one of the best mobile gambling experiences although the desktop version is also well-developed with excellent quality and features.

New users get a 100% match bonus on their first deposit of up to £100. It also offers a reasonable playthrough requirement of just 30x the bonus. Users also get another £1400 in their first week if they take a look at the Premium Welcome Package.

Spin Casino

Spin Casino offers up to a £1000 free bonus on initial deposits plus a 100% deposit match offer covering the first three deposits. It offers an excellent mobile-friendly website allowing users to access it via their mobile phones and tablets. It has an impressive layout and great layout and menus.


While Matt Damon may be a gambling lover, he represents a fraction of many movie stars and celebrities that have openly shown their fascination and support for the gambling industry has generally attracted. Damon’s interest in gambling was birthed out of his acting career and has continued many years after he first played Mike McDermott in Rounders.

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