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The Top Five Gambling TV Show Episodes

The Top Five Gambling TV Show Episodes

Historically,  television has always enjoyed a strong relationship with gambling, either as part of a joke or simply a great plot device. There is a perfectly good reason for this, few leisurely pursuits stir the emotions as much as gambling. We’re talking mob bosses, cowboys, politicians or just a group of friends, gambling, at home or in the casino. Such story lines can lead characters into trouble or into humours situations but what we can be sure of is that writers will continuously return this awesome plot device because it always delivers. Yes, gambling in television shows has brought us many memorable moments, our favourites of which we have listed below.

Boardwalk Empire

HBO’s period classic Boardwalk Empire was another to lean heavily on gambling, like this poker classic from Season 4. Arnold Rothstein, Meyer Lansky, both real-life historical gangsters, are playing with Nucky Thompson at the five-card draw tables. It’s Nucky’s establishment and after an extremely well scripted table chat, Rothstein, “taking a long time to lose”, needs to react to his opponent’s raise. In doing so, he duly borrows a $200,000 marker from the house, essentially borrowing from Nucky himself. What does he do with it? He moves all in despite holding nothing, only to see Thompson call with a queen-high flush leaving Rothstein to call it a night against the old enemy. In real life, Rothstein would be shot and killed during a poker game at the Park Central Hotel in Manhattan New York. Reportedly, Rothstein had nothing good in his final hand then either.


There are two main gambling threads to Friends. Firstly, the was an episode where the chums all played poker and Ross annoyingly let Rachel win. And secondly, 'The One in Vegas' where they all head off to Sin City. Another of their group, Joey, is already out there but not, as the gang believe, filming a movie, but rather working as a gladiator in one of the casinos. Once there, Phoebe makes a beeline for the slots where she’s hawked by a lurker, a vulture like slots strategy, where one observes which machine will payout first. On the hand, rather than enjoying a romantic weekend, Monica and Chandler instead have a falling out. However, things are soon resolved following a run of good luck at the craps table after which the pair bet everything on the throw of a dice end up agreeing to marry at a nearby 24-hour chapel. Before they get to tie the knot though, they bump Ross and Rachel who drunkenly bust through the chapel doors as husband and wife.


Based on a true story, the demise of real life character Wild Bill Hickok is brilliantly executed over a game of poker. Although only appearing in the early few episodes, Keith Carradine’s Wild Bill spends almost all of his air time playing poker. In his earliest scenes, he not only gains a perfect read on one particular opponent, a drunken lout played by Garret Dillahunt, he also verbally destroys him, before taking his money. Said lout, Jack McCall, later shoots Wild Bill in the back in a scene that is intercut with the gruesome arrival of a miner riding on horseback and carrying the head of a Native American chief, amplifying how fast the Deadwood camp’s prospects were always able to change for the worse.

It’s Always Sunny In Philadelphia

It’s Always Sunny In Philadelphia has been running for over 14 seasons and has never failed to raise a laugh in that time. Also, over that time, the show has included a few gambling threads. Like Frank betting on kids’ basketball games or playing high stakes poker with his Vietnamese buddies or for even higher stakes when, in the same episode, they head down to the basement to play Russian Roulette. The best gambling storyline, however, came in the episode “The gang get stranded in the woods”. The episode starts out as a road trip to Atlantic City but things soon go wrong when they crash the vehicle into a tree and become stranded. Charlie and Dennis set off to find help and end up hitching a truck ride to AC after Dennis convinces Charlie to “say yes”, which, by the time they reach AC, works rather well in the casino as Charlie continues to say yes. This time, winning $15,000 at the roulette table, betting it all on black and letting it ride, a risky roulette strategy to say the least. Nevertheless, such is the point of this very funny episode, the gamble pays off big time and the two of them spend the night boozing with baseball players before spending Charlie’s remaining winnings by taking a private jet back to Philadelphia.

The Sopranos

The third HBO show on the list, The Sopranos is considered by many to be the finest TV show of all time. Set in New Jersey, this is Goodfellas under the microscope, a show so deep we get to see every bit of anguish suffered by mob boss Tony Soprano bought on, not only by his crew, but also by his wife and kids. As you might expect, his power, money and wealth lead the show’s anti-hero to find other outlets for his attention such as womanising, drinking, eating (there is always food in The Sopranos) and gambling. In one episode Tony is betting exorbitant amounts on casino games and sports and losing heavily, explaining to his therapist "It's a big part of my life. I need the risk". In another he leads another parent, and old school friend, into murky waters through high stake poker games, some of which are attended by Frank Sinatra Junior himself.

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The Top Five Gambling TV Show Episodes



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