If you placed a bet that the gambling blog was going to happen this week, you are a winner! Your funds should already be in your DraftKings account.
When mobile sports betting became legal in Massachusetts recently, I had the idea to do a piece about gambling movies. I did NOT come up with the title “Bets Pictures,” but I wish I did!
Stories, and therefore movies in general, are conflict driven. Normal human behavior regularly creates conflict in many forms. When you involve our so-called “vices,” alcohol, sex, drugs, gambling…the conflicts multiply and multiply.
Addiction is serious business, no matter what the focus of the addiction happens to be, so movies about addiction tend to stay away from comedy. Not too many addiction comedies out there. They’re there, but they’re few and far between.
What I’ve assembled for you today are ten of my favorite movies about gambling. I’m not saying they’re the best movies about gambling, just ten films that deal with the subject that I would highly recommend.
Since this is all about gambling, you can now place your bets! I am setting two over/under bets for you. If you’re up on gambling terms, you know exactly what I’m talking about. If you don’t know what an over/under bet is, maybe you need to watch more gambling movies.
Here are the choices for you. There are 10 movies on today’s list. The over/under for Oscar nominations is 18. The over/under for Oscar wins is 10. Make those wagers, and on we go.
I decided not to include any of the Oceans movies because I consider them to be more casino heist movies than gambling movies. Certainly, gambling is involved, but I didn’t include them. Our guys really aren’t doing much gambling at all. Robbing yes. Gambling no.
I also didn’t include 21, which is a decent gambling movie, but it carries the Kevin Spacey stink, so I will skip it. Maverick is also a decent gambling western, but Mel Gibson, so…
Well, actually, while I’m at it…
Rain Man is an excellent film. Tom Cruise’s best performance ever. Hands down. I think of a lot of things when I think of this movie, but gambling isn’t one of them for some reason. So it’s not here.
I absolutely hated The Color of Money. One of the worst Oscar make-up calls in history, and not even half as good as the 1961 film that introduced us to Fast Eddie Felson. That 1961 film is on today’s list.
Two for the Money is a laughably bad “drama” about sports gambling starring scenery eaters Al Pacino and Matthew McConaughey. Skip that one if you ever get the chance.
Also skip Vegas Vacation. Remember when I mentioned that there aren’t any really good gambling comedies. This movie exists, and that statement is still true.
I was never a fan of Casino. I know they’re not the same type of movie, but my Scorsese, DeNiro, Pesci choice will always be Goodfellas.
Other decent films that were considered for this list included 1974’s The Gambler starring James Caan as a gambling addicted literature professor who loses it all. Another good bet (you see what I did there?) is Paul Thomas Anderson’s Hard Eight from 1996 starring the late great Phillip Baker Hall (Mr. Bookman!) as a professional gambler teaching the trade to protege John C. Reilly. This is pretty bleak all the way around.
A gambling comedy that almost works and is definitely worth a laugh or two is The House from 2017 starring Amy Poehler and Will Ferrell as parents who open an illegal casino in a friend’s house when their daughter’s college scholarship is taken away. Key word here is almost. I’ll set the over/under at 3.5 laughs for you. Paul Blart: Mall Cop did NOT get those odds!
Guy Ritchie’s 1998 Lock, Stock, and Two Smoking Barrels was the odd movie out when I put this list of ten together. I love it, and I do consider it a gambling movie, but the gambling isn’t the center of the film, so it was the last film to be eliminated from contention.
Here are the ten that did make the cut. Will your favorite gambling movie be here? You may be able to find that on FanDuel! Place your bets, and let’s get started!
Rounders (1998)
In this poker drama Matt Damon plays reformed gambler Mike who needs to get back into the game when his lowlife friend Worm (Edward Norton) gets into trouble. John Malkovich eats Oreos and the scenery in equal amounts as Teddy KGB.
There’s nobody to really root for here as everyone involved is either an addict or an enabler. When Mike and Worm get beat up, you can't help but think they deserve it. This has an overall sleaze to it that adds to its appeal. The card playing is informative since Damon narrates a bunch of it. This is dreary, and the addiction part of the movie is realistic.
Malkovich’s accent is anything but realistic. “Gife the mane hees maney!” Check out a clip on YouTube. It’s comical.
California Split (1974)
I hadn’t seen this in a long time, so I wanted to give it another spin of the old roulette wheel. California Split stars George Segal and Elliot Gould. One a casual gambler, the other a pro. When they become friends, both of their lives take a downward turn.
This drama features casino games and horse racing and the pair do their share of both winning and losing. But it’s mostly losing. And they also get beat up. When gambling is involved, a lot of people end up getting beat up. Or worse.
Segal and Gould are rather likable until the losses start piling up. In these films, characters are always in super desperation mode, and they constantly make bad decisions. We can see it. They can’t. Very much like addiction.
Croupier (1999)
When walking into a casino at the start of the film the title character Jack (played by Clive Owen) says to himself, “Welcome back, Jack. To the house of addiction.” Jack is more than familiar with this particular house, and now he’s back. As a croupier.
Jack is an aspiring writer and thinks that the life of a croupier would make for an interesting novel. Based on the events of this film, the life of a croupier would make for a hell of a novel.
When Jack begins dating a customer at the casino (a serious violation of casino rules) things start getting complicated. He’s then recruited to be the inside man for a casino heist.
Even though there’s a heist involved, the fact that Jack is a writer studying the casino and its patrons, the film is focused on just that. We are privy to all of Jack’s thoughts about gamblers and gambling.
This is well done all the way around. I was surprised it didn’t receive any Oscar nominations, but then read that it was ineligible because it was shown on Dutch TV! Those meddling Dutch!
The tagline for Croupier is “Life’s a gamble.” Indeed!
Molly’s Game (2017)
This film, starring Jessica Chastain, has one of the best beginnings (cold opens) in recent memory. Molly’s Game tells the amazing true story of Molly Bloom, an Olympic-class skier who ended up running the world’s most exclusive high-stakes poker game and was later targeted by the FBI.
So there’s a lot there to unpack there. I usually loathe Aaron Sorkin, but he wrote this screenplay and it was nominated for an Oscar and I liked this movie, so one for Sorkin here.
Molly is extremely strong and strikes an intimidating pose at times as the game runner, but she also has a vulnerable side to her that’s just as interesting. She’s caring and compassionate toward her players and looks out for their best interests. She tries to tell a player when she thinks they have had enough, but….addiction…
The desperation is once again in full bloom as gamblers play for hundreds of thousands of dollars. Character actor Bill Camp is tremendous as an out-of-control gambler who is on a terrible losing streak. Seeing him come up to Molly and asking for another $100,000 over and over is like watching a car wreck. You know he has no way of repaying this money, and bad things happen to people who don’t pay their gambling debts.
Molly’s life begins to unravel when she starts abusing drugs. Her addiction in her world of addiction eventually brings her down. You see it coming from a mile away, but Molly can’t. Addiction.
An odd resolution, in my opinion, but you can’t change much of a true story.
Unless, of course, you're Quentin Tarantino. Stop that, by the way!
Bob le Flambeur (1940)
“I was born with the Ace of Diamonds in my hand.” So says aging gambler Bob Montagne in this French classic from the great director Jean-Pierre Melville. Bob is our title character, which translates to “Bob the High Roller.”
This high roller has hit rock bottom after a big loss though, and he decides to assemble a team to rob a casino. Seems like everyone wants to rob a casino!
Bob le Flambeur is the favorite film of directors Jim Jarmusch and Paul Thomas Anderson. Speaking of Tarantino, it’s his favorite gangster film. It’s considered the precursor to the French New Wave in cinema that happened in the late 50’s. It also directly inspired the Transporter film series with its portrayal of a close relationship between a criminal and a police officer.
There’s a lot to love here, especially if you enjoy French cinema. I won’t spoil the end, but these things rarely end well for those involved. I’ll leave it at that. You should see this for yourself. I bet you’ll love it!
“Lady Luck, his mistress, made him forget why he came.”
The Cooler (2003)
After rewatching all of these films (and others that didn’t make the cut) filled with streaks (good and bad) and runs of luck (good and bad), I started wondering if luck is at the root of a majority of this entire enterprise.
Yes, you can know the games inside and out. Yes, you can have years and years of experience. But the cards are still the cards and that little roulette ball ends up in the spot it is destined to whether you like it or not.
The Cooler is about luck and streaks, but in kind of a reverse way. The always reliable William H. Macy plays Bernie Lootz. Bernie is a loser at gambling, and quite possibly at life. He has such bad luck that he’s hired by casino boss Shelly Kaplow (Oscar nominated Alec Baldwin) as a “Cooler.” A “cooler” is someone whose luck is so abysmal, that it rubs off on others.
Any time there’s someone winning big in the casino, Shelly sends in Bernie. All he needs to do is hang around the winner, and Abracadabra, they suddenly start losing. Problem solved.
I really don’t know much about gambling and casinos. Is this a real thing? Do casinos hire “coolers?” It all seems pretty superstitious and silly, but this movie is extremely compelling nonetheless.
Macy is, of course, a sympathetic character. You’re rooting for him from the start. When he starts dating a cocktail waitress played by Maria Bello, you assume his luck is changing!
Bernie also thinks his luck is changing, and wants to quit his job and move on to a better life. This does not sit well with Shelly. At all. There’s also some nasty business with Bernie’s estranged son showing up. You smell a scam on that kid from the start.
Baldwin is, at times, terrifying as the casino boss. Even when he’s not hitting people with lead pipes.
The Hustler (1961)
I mentioned The Color of Money earlier and how much I disliked it. I often despise blatant Oscar “make up awards.” You see me, The Departed? Actually, no real surprise since The Color of Money is a sequel of sorts to this film that I happen to love.
Pool is the name of the game here, and Paul Newman’s “Fast” Eddie Felson is out to prove he’s the best of the best. When you’re trying to prove yourself in such a fashion you go after the biggest fish in the pool hall, and in this pool hall that fish is Minnesota Fats (played by Jackie Gleason).
The Hustler earned 9 Oscar Nominations, including four acting nominations (Newman, Gleason, Piper Laurie, and George C. Scott), a Best Picture nomination and one for director Robert Rossen. George C. Scott refused to even be nominated, but that’s another story for another day.
The film won two Academy Awards. One for Cinematography (black & white), and Art Direction-Set Decoration (black & white). I’ve always thought it was interesting that they had separate awards for black & white and color films for several years. Not sure why they felt the need to do that. Silent films went up against “talkies” back in the day and competed in the same category. I may have to look into that.
All of these Oscar nominations were well deserved, and I’m surprised it didn’t win more than two. This film is a great character study of both Felson and, to a lesser extent, Fats. Gleason’s riveting appearances bookends the film with epic pool matches (99% of the shots taken by Newman and Gleason themselves) featuring excellent pacing and cinematography.
The Hustler was shot mostly on location in New York City, giving everything a gritty authenticity that enhances all of the performances. The first of the two contests between the two sees Eddie up $18,000 before losing it all. Eddie then hits the inevitable downward spiral that includes a mobster breaking his thumbs. After recovering, he takes his last $3,000 back to the pool hall looking for Fats. One game for all of the money, hoping Fats can finish him off quickly and put him out of his misery.
This is pretty bleak stuff here. Come for the two pool matches, stay for all of the incredible performances throughout.
The Cincinnati Kid (1965)
Steve McQueen takes Ann Margaret to a cockfight in this movie. I don’t think I need to say anything else.
I’ll add that this is an excellent film, and another great character study. Steve Mcqueen is the Cincinnati Kid, “an up-and-coming poker player who tries to prove himself in a high-stakes match against a long-time master of the game.” IMDb
That master of the game is played by old friend of Cinema Wellman, Edward G. Robinson. An all-time favorite around here. The supporting cast (Rip Torn, Tuesday Weld, Joan Blondell, Karl Malden) is also phenomenal in a movie that features plenty of intense poker playing suspense and drama. This is hard to watch at times, as is the next movie on our list.
As always, I won’t spoil anything. I’ll save that for our new series, “Spoiler Alert!” and now that I think of that, that’ll be next week’s episode. I’ll “ruin” all of these movies by spilling all of those beans and letting all cats out of all bags. Skip that one if you want to see any of these first.
Uncut Gems (2020)
I want to be up front about something before I start this one. I have never been a fan of Adam Sandler. Nothing against him personally, of course. I’ve heard he’s a great guy who is very generous. I just never liked any of his characters on “SNL” and never thought he was funny.
I was intrigued when I saw Uncut Gems advertised. Once again, I’ll go to IMDb for an assist, “With his debts mounting and angry collectors closing in, a fast-talking New York City jeweler risks everything in hope of staying afloat and alive.” Does that sound like Adam Sandler to you? Opera Man? Cajun Man? Canteen Man?
I was pleasantly surprised by this movie and his performance. It’s a tad long (2:15), but I believe it’s because the filmmakers wanted to prolong our look into the chaotic madness that is the life of Howard Ratner.
To say there’s a lot going on in this movie is an understatement. I understand the complaints that the dialogue is all over the place and sometimes the yelling is distracting. I think it’s a realistic look into the life of a degenerate gambler who is willing to risk anything and everything in search of that big win.
This is sometimes very hard to watch, but it’s compelling filmmaking with a realistic look at addiction and what it can do to a person. When a million-dollar basketball parlay bet begins with who wins the opening tip-off, you know things are going to get ugly.
I look forward to spoiling this next week.
And now, the final film on today’s list. By leaps and bounds the lightest movie in the bunch. There are actually several parts of it that are quite funny, so I think it’s a perfect place to finish.
The Sting (1973)
This film has an amazing Oscar winning percentage. It was nominated for 10 awards and won 7. There aren’t many movies out there that can beat those totals.
I do realize that this Best Picture winner is more of a “gambling adjacent movie” as opposed to a full on “gambling movie,” but I didn’t want this entire list to be such a downer. And when I researched gambling movies on the Interwebs, The Sting was on just about every list. So it counts. :)
Paul Newman once again. This time with his old pal Robert Redford in a depression era story that single handedly resurrected ragtime music when it was released in 1973.
Newman is Henry Gondorff and Redford is Johnny Hooker. The pair of grifters team up to pull off the ultimate con and take the money of big-time gambler Doyle Lonnegan played by Captain Quint himself, Robert Shaw. Harold Gould, Ray Walston, Charles Durning, and Eileen Brennan co-star in this delightful con game of a movie that will keep you guessing like a good murder mystery.
I love this movie and watch it regularly. Such a fun time.
Well how did you do with your wagers? The over/under for total Oscar nominations was set at 18 and the O/U for total Oscar wins was set at 10. The actual numbers were 21 nominations and 9 wins. How did you do? Were you more of a Bernie or a Henry?
That’s it for this week! We hope you return next week for a “Spoiler Alert!” blog that will “ruin” today’s movies. No spoilers this week, all of them next week.
If you don’t want things spoiled, skip next week! I totally understand. But please return the following week for the Best and Worst of April’s screenings!
Until then…take care.
