Every week at SiftPop.com, we challenge our writers to choose what they think is the best movie under a certain topic related to a recent release. So this week, with the release of The Card Counter, we’re counting down our favorite gambling movies! Let us know @SiftPop what your ranking is!
Sometimes old habits die hard, and in the case of law student and reformed gambler Mike McDermott (Matt Damon), all he will need is a slight push to get back into the world of high-stakes poker. In this case, when his old troublesome friend calls upon his help in order to settle a hefty prison debt, this is all the motivation that Mike will need in order to fall back into his old ways. Rounders, directed by John Dahl, stars Damon, Edward Norton, and Gretchen Mol. Of all the movies that concern poker, I find this one the most intriguing due to its stellar cast, authenticity, characters, and solid use of tension. The stress-inducing high stakes games keep you locked in and you can’t help but back Mike as he plays his way to relieve Worm’s (Norton) debt and redeem himself as a poker player. John Malkovich is picture perfect as the antagonist, Teddy KGB, and you anticipate him getting his comeuppance throughout this film. Teddy is ruthless and uncaring about ripping Mike’s savings from him and doesn’t care about Worm’s dilemma in the slightest, he lives to crush hopes and dreams. The rush of Mike and Worm attempting to pay off 15 grand in a measly five days is a roller coaster ride to say the very least. Of the plethora of films that sit at the poker table, Rounders is a royal flush. (Joe Vargas)
Somehow, Paul Thomas Anderson showed his filmmaking prowess from the very start of his career with his debut feature, Hard Eight. It tells the story of the down-on-his-luck John (John C. Reilly), who just wants a not insignificant sum of money for his mother’s funeral, and Sydney (Philip Baker Hall), who decides to take a chance on John and bring him under his wing in this time of need. This, of course, fits this week’s topic because John attempts to make his money gambling at casinos. And that’s where Anderson’s skill is on full display. The theme and setting are inextricably linked to each other and that makes the film a rewarding and fulfilling watch. It’s definitely not the best work of someone who’s made movies like Magnolia and There Will Be Blood, but it doesn’t feel like Anderson’s just getting his feet wet with filmmaking either. He dove in head first and showed the world what he was capable of in this great debut gambling flick. (Robert Bouffard)
I have no idea how many times I’ve seen Lock, Stock and Two Smoking Barrels, but it’s a lot. Make no mistake, it is perfect and one of the most impeccable scripts ever put to film. The British underworld is director Guy Ritchie’s (great surname) wheelhouse. It’s all centered on a corrupted game of poker, and with no less than six groups of gangster characters to intertwine and weave into one cohesive story, the filmmanages to pull it off with such aplomb you shake your head in wonder at how it was managed. I love all of Ritchie’s films set in this genre, but Lock, Stock is still his best. It’s filled with great characters, great, endlessly quotable one-liners, and a perfect bitter sweet did they/didn’t they ending. (Adam Ritchie)
I always appreciate sweet, and ultimately wholesome movies, and the four-time Oscar winner (including Best Picture) Rain Man is no exception. It stars Tom Cruise as Charlie Babbitt, a young man who learns he has an older brother after the death of their father. Their father left the largest part of his estate to Raymond (Dustin Hoffman), Charlie’s brother, who is autistic and very routine-oriented. So Charlie goes to meet Raymond with the hopes of coercing him out of some or all of the hefty sum that his father left. But over the course of the film, the newfound brothers develop a beautiful rapport that leads to an emotional and heartfelt ending. Hoffman gives a great performance and I always enjoy seeing Cruise in his days before all of his movies were action flicks trying to one-up his last project. Featuring a key scene in which Raymond counts cards to win a hefty sum of cash, Rain Man is certainly one that’s worth checking out. (Robert Bouffard)
When I saw this week’s topic was gambling movies, I had to jump on the chance to write about Uncut Gems. I’ve been a Sandler fan for many years, and yes, while he has had a lot of misses, the dude knows his audience and target demographic. When the Safdies came along with this script that they spent so many years trying to get Sandler to do, the results paid off and gave us a performance from him that finally got people talking about him as a serious actor. Sandler plays a smooth talking, gambling addicted, jewelry story owner who is always trying to stay one step ahead of the people he owes money to, and combined with an almost anxiety inducing score, this movie soars. I can’t recommend this movie enough. It is an experience and a half. (Frank Kemp)
The James Bond franchise is the longest ongoing Hollywood franchise, dating all the way back to 1962, with Casino Royale being considered by many to be one of the best movies this series has ever produced. In almost 60 years, this was the one time the franchise pulled a reboot as it went back to tell the origin adventure for our debonair super spy, and introduced him to a new generation of moviegoers. Sandwiched in between international acts of espionage, terrorist organizations looking to disrupt the stock market and political relations, and intense action sequences lies one of the greatest poker sequences ever put to film. For almost 30 minutes of straight runtime, we see the ups and downs of high-stakes Texas hold ‘em poker. The film drops just enough exposition so that uninitiated viewers can understand the game, while bringing dramatic tension through bluffs, raises, folds, and a climactic final hand that all movie fans can enjoy. Casino Royale is a high recommendation for any fan of James Bond, action films, or gambling extravaganzas. (Heath Lynch)
Yes, the “other” De Niro and Pesci mob movie directed by Martin Scorsese in the ‘90s. Casino follows a pair of mobsters, played by Robert De Niro and Joe Pesci, who go out to Vegas to make their mark in the lucrative gambling scene. The pair have their bond tested by Sin City and the arrival of Sharon Stone’s Ginger into the picture. Though I think the public perception of Casino can be a bit pejorative, as just Goodfellas’ not-quite-as-good cousin, this gangster epic has plenty going for it in its own right. It earned an Oscar nod and sits in IMDb’s Top 250 (at 143). Aside from Scorsese’s masterful work behind the camera, our trio of leads are all fantastic. We already knew De Niro and Pesci were great together, but Stone more than holds her own here. Her career at times can sometimes just get reduced down to her role in Basic Instinct, but going toe-to-toe with De Niro and Pesci is no small feat. If you’ve shrugged this Vegas epic off as Goodfellas light, give it a shot. (Jake Bourgeois)
Ocean’s Eleven proves you can make an amazing heist film with a giant cast and make it impactful for all crew members, tense, and fun. George Clooney’s Danny Ocean is the man for this team and he plays it cool every step of the way. This was the first movie I saw Clooney in where I thought he could be a legit movie star. Yes, I understand Batman and Robin showed Clooney can be in a blockbuster and Out of Sight showed he can be a lead in a movie. This however proved Clooney was no slouch when it comes to blockbuster leading men. Ocean’s crew is a murders row of Hollywood A-listers ranging from Brad Pitt, Matt Damon, and Don Cheadle to Casey Affleck, Scott Caan, and Eliot Gould. There are also great turns from the late greats Bernie Mac and Carl Reiner. Andy Garcia is terrifying as Terry Benedict, the mark being targeted by Ocean and his crew. All around, Ocean’s Eleven rides a wave of a great heist that doesn’t have any violence and focuses exclusively on the tasks at hand. It’s a precision masterpiece that sets the standard for modern heist, gambling, casino, and ensemble pieces. (Mike Hilty)
What do you get when you throw Paul Newman, George C Scott, Piper Laurie, and Jackie Gleason all into one film? A classic, of course. The world of grifting and gambling come to a head in this drama seeped with loathsome beings and tragic stories. When the money is thrown around a pool hall, anything goes. A smart, but arrogant young man named “Fast” Eddie, played with incredible zeal by Newman, wants to become the greatest of all time… but that means he has to take down the best. Who is the best? Minnesota Fats, that’s who! Gleason is a compelling and cool force who never lets you see him sweat. Eddie’s white whale is in his sights, but with a tragic love affair of toxic proportions with Laurie as well as the sneaking “helping hand” of Scott in his way, will he ever reach the mountain top? You will have to check out Robert Rossen’s classic drama to experience every cheer, tear, and leer along the way. (Shane Conto)
Do you enjoy seeing a story about a great confidence artist? Or more simply put, do you like con movies? Then let me introduce you to the granddaddy of them all, the best con movie ever made, and winner of Best Picture at the Oscars, The Sting. This picture is loaded with an all-star cast that is highlighted by Robert Redford, Robert Shaw, and the ever charismatic Paul Newman. It is set in Chicago against the backdrop of the Great Depression, and it showcases the lifestyle of grifting. Whether it is simply being a pickpocket artist, or robbing the biggest mobsters in America, this movie has it all. What’s even more fascinating is that the big con is convincing other people to gamble away their money in poker and on rigged horse racing bets. There’s gambling within the confidence game. There’s layers upon layers of depth to this story. Group these with the stellar performances, great art direction, and even the timeless score from Marvin Hamlisch giving us classics like “The Entertainer,” and you have yourself an all-timer. Be sure to watch The Sting today. (Heath Lynch)
The Color of Money
Often regarded as “the lesser” sequel to The Hustler, The Color of Money is anything but that. And I think there are precisely three reasons for that — Martin Scorsese, Tom Cruise and last, but certainly not least, Paul Newman. When you get this kind of ensemble in the capable hands of Scorsese, who by that time (1986) more than proved himself, you can’t go wrong. And yet, plenty of fans often regard this as a “not that great” movie or just straight up dismiss it. So, why is that? I think it’s because they expected Scorsese to “continue” with this sequel one way, but he did it in his style. But most importantly, he succeeded in making this its own thing. Scorsese made this film in such a clever way that if you watch it, not knowing it’s a sequel to The Hustler, you will still enjoy it nonetheless. Unlike other sequels, knowledge of the original is a plus, not a necessity. The Color of Money is a fast-paced, entertaining film that finally got the well deserved Academy Award for Paul Newman (his only one, if you don’t count the “honorary Oscar” he got the year before). Plus, this is the very first time I believe Tom Cruise was taken seriously as an actor, even though he had a tough challenge, “going up” against one of the finest actors ever. The Color of Money might not be the best gambling movie ever, but it’s entertaining, fast-paced, and overall a really enjoyable piece of a film. The “master teaches his young apprentice” formula in this film just works and works so well. (Luke Burian)
The Hangover
The Hangover is a 2009 movie about four friends: Doug (Justin Bartha), Phil (Bradley Cooper), Stu (Ed Helms), and Alan (Zach Galifianakis), who all go to Las Vegas for Doug’s bachelor party and wake up the next morning with no Doug and no memory of the night before. The movie was successful enough to spawn two sequels, but rewatching it today, yes, there are still some funny moments, but there are terribly dated jokes that make this film not as good. Todd Phillips directs and takes us on the guys’ wild night very cleverly by solving the puzzle of the clues they can find. There is a brilliant card counting scene that takes place towards the end of the movie that shows how useful Alan can be, when up to this point, he had been the comic relief of the group. Another good thing is the film starts toward the end of the story and tells us how they got to that point, which works well for most stories, but kind of spoils the story. One question I have seen posed to this movie and its sequels is, why do drugs that would render most people unconscious if ingested at the quantities these characters consume, when it causes them to black out and go completely wild? If you want to check out the trilogy, they are all currently available to stream on HBO Max. (Austen Terry)
Snatch
“D’ya like dags?” Often mentioned in the same breath as Lock, Stock and Two Smoking Barrels, Snatch is Guy Ritchie’s second feature film, and according to some people, his best. The movie revolves around a priceless, stolen diamond and the parties interested in obtaining it. The setting is a network of bookmakers, boxing promoters, and otherwise bumbling criminals. Brad Pitt makes an appearance that features perhaps the best and also worst Irish accent ever put to film at the same time, and Lock, Stock alums Jason Statham, Vinnie Jones, and Jason Flemyng return for some more patented Ritchie interwoven storylines that ultimately come together in a deeply satisfying conclusion. I would say these are the kinds of movies Guy Ritchie doesn’t make anymore in favor of big Hollywood productions like Aladdin, but I would be remiss not to mention the excellent The Gentlemen from a few years ago in this space, as well. (Chris Bakker)
Molly’s Game
The main reasons anyone should watch this film number two: Jessica Chastain and Aaron Sorkin. However, before we get into that, let’s talk about what this movie is about and how it fits in here. The story follows Molly Bloom, who finds herself evading the FBI after they take an interest in the high-stakes poker game she runs for celebrities and high-ranking members of the underworld. Now, if you’re a fan of Sorkin, no matter what, you’re guaranteed to have a good time in this one. It’s got all the Sorkinisms, from high-ranking conspiracies, over-cerebral walk and talks, and higher-than-reality characters. They captivate, they intrigue, and they’re often played by actors that could hold their own in any scene — to wit, watching them work is an absolute blast, and this is no exception. Now, Sorkin’s strengths as a writer have seldom been scrutinized, but the real question here was around his ability as a director, and it was proven with the great job he did right out of the gate. Coming back to the cast, Chastain really leads this film with an iron fist, ensuring no one chews away her scenery; it really is a sight to be seen. Plus, if you’re a fan of the mechanics of gambling, from the seedy backdoor games, to the high-adrenaline, high-stakes exclusive circles, this is a movie that’s sure to get your blood flowing. Overall, this is a high recommendation for all who love to spectate a true battle of wits, and solid powerhouse performances. (Alice-Ginevra Micheli)
Seabiscuit
Inspired by a true story and based on the book by Laura Hillenbrand is the 2003 sports film Seabiscuit,directed by Gary Ross.This is a classic tale, starring Tobey Maguire, Jeff Bridges, and Chris Cooper that has a lot of heart as the film is set in the midst of the Great Depression. Maguire stars as Johnny “Red” Pollard who wants to get into horse racing after the tragic death of his son and a divorce from his wife. Red is a natural around horses, but because of his tough upbringing during the depression, he is a very bitter young man. He meets the underdogs who can help set him up for success and teams up one of the most notorious thoroughbreds in horse racing history. The film is inspiring with a strong story and cast that excels with a theme of perseverance, and there will not be a dry eye while watching this film. Seabiscuit is stereotyped to be a film audiences have seen before, but it is sure to make you feel good after watching. It is a crowd pleaser for general audiences. (Kristin Ciliberto)
Mississippi Grind
A man told me once that you’ve got to know when to hold them, know when to fold them, know when to walk away, know when to run. However, when you’re presented with a film from A24, you go all in. Thus, with Mississippi Grind,I decided to roll the dice. Starring Ryan Reynolds alongside Ben Mendelsohn, this is a story of two men who decide to gamble their way down the Mississippi rife with just as much symbolism as it is with gambling. This story is beautifully shot and is as enrapturing as it is depressing. Reynolds brings an air of charisma to this film that gives it a boost, while Mendelsohn and the rest of the cast provide a series of deep, enrapturing, and at times heartbreaking characters, especially with Gerry and Curtis, both of whom have problems that they clearly aren’t willing to face. It serves just as much as a source of entertainment as it can a wake up call. If you somehow are like me and haven’t seen this film until now, then you’re making a safe bet on this movie. P.S. on a serious note: compulsive gambling and gambling addiction is a real and serious problem. Don’t be afraid to seek help. (Joseph Davis)
The Cooler
The Cooler takes a small look at the seedier side of casinos. The house is actively rooting for you to lose and at times, will stack more than just the chips against you. William H. Macy plays Bernie Lootz, who works as a cooler when other patrons of the gamble start a hot streak. Bernie’s job is to go sit down at the table and suck up all the luck, allowing the casino to win their money back. He… cools the table, you see. Everything turns around once Bernie finds love and, instead of cooling off others, he seemingly increases their odds of winning. Bernie then has to decide between a happy romantic life or continuing his sad sack job of costing others. This is a fun role for Macy to take on as a majority of his roles seems to be the punching bag. It’s nice to see him attempt to be happy for a change. (Scott Batchelor)
Rat Race
When someone says, “tell me about a movie with gambling in it,” a normal person might say Ocean’s 11 or The Sting. While those are great movies and will surely rank higher on this particular list, 2001’s Rat Race is the movie that pops into my abnormal head. This incredibly silly, star-studded movie has gambling at its heart and showcases its lighter side. High stakes gambling by a bunch of rich tycoons led by the always hilarious John Cleese. The plot of the movie is to send 12 random, yet awful people across the country on a race and bet on who gets there first. The best moments of gambling and comedy come from the hilarious asides where the rich people are killing time waiting for the race to end by betting on random things, from how much a prostitute will charge for a Pepto-Bismol bath and back shave, who will vomit first in a turbulent airplane, or which maid will be able to hang on the curtain rod the longest. There are a ton of other silly moments as well, like an unfortunate cow going on a hot air balloon ride and a tour bus full of I Love Lucy impersonators. Lastly, if I had a nickel for every movie, featuring Smash Mouth’s All Star in the summer of 2001, I’d have two nickels, which isn’t a lot, but it’s weird that it happened twice, right? (Nick Ferro)
21
Guilty pleasure that I can’t stop returning to. That sentence defines this movie for me. I am unapologetically a math nerd who is simultaneously as good at playing cards as Michael Jordan was at baseball. I first watched this film with a roommate in college. A week later, while on a trip for a conference, we found ourselves at Harrah’s Casino in New Orleans, where we both promptly lost every dollar of per diem we had been given by playing blackjack. At this point, I started questioning Ben’s methods and what I had “learned.” Regardless of that failure of a trip, I still have so much fun watching Jacob Pitts play a perfectly smarmy jerk, while also witnessing Laurence Fishburne use all of his intimidation presence possible sans an uplink to the matrix or running a group of carrier pigeons to hold down the fort for John Wick. Kevin Spacey aside, take some time to watch an incredibly underrated cast give Micky Rosa his comeuppance. 21 is easily a fun film to throw on while you play your favorite card game on your phone! (Matt Lawson)
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