Movies Like Win It All
If you loved Win It All's Comedy storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.
★ Top Picks
California Split
Carefree single guy Charlie Waters rooms with two lovely prostitutes, Barbara Miller and Susan Peters, and lives to gamble. Along with his glum betting buddy, Bill Denny, Charlie sets out on a gambling streak in search of the ever-elusive big payday. While Charlie and Bill have some lucky moments, they also have to contend with serious setbacks that threaten to derail their hedonistic betting binge.
Easy Money
To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.
Two for the Money
A former college athlete joins forces with a sports consultant to handicap football games for high-rolling gamblers.
Poolhall Junkies
A retired pool hustler is forced to pick up the stick again when his brother starts a game he can't finish.
What Happens in Vegas
During a wild vacation in Las Vegas, career woman Joy McNally and playboy Jack Fuller come to the sober realization that they have married each other after a night of drunken abandon. They are then compelled, for legal reasons, to live life as a couple for a limited period of time. At stake is a large amount of money.
Let It Ride
An average kind of guy who has a slight problem with gambling goes to the track, and mystically, it seems as though he can't lose, no matter how he bets; and he has an incredible day.
Mississippi Grind
Gerry is a talented but down-on-his-luck gambler whose fortunes begin to change when he meets Curtis, a younger, highly charismatic poker player. The two strike up an immediate friendship and Gerry quickly persuades his new friend to accompany him on a road trip to a legendary high stakes poker game in New Orleans. As they make their way down the Mississippi River, Gerry and Curtis manage to find themselves in just about every bar, racetrack, casino, and pool hall they can find, experiencing both incredible highs and dispiriting lows, but ultimately forging a deep and genuine bond that will stay with them long after their adventure is over.
This Is 40
Pete and Debbie are both about to turn 40, their kids hate each other, both of their businesses are failing, they're on the verge of losing their house, and their relationship is threatening to fall apart.
More Movies Like Win It All
Vegas Vacation
The Griswold family hits the road again for a typically ill-fated vacation, this time to the glitzy mecca of slots and showgirls—Las Vegas.
Dirty Rotten Scoundrels
Con artist Lawrence Jamieson is a longtime resident of a luxurious coastal resort, where he enjoys the lavish fruits of his deceptions -- that is, until a competitor, Freddy Benson, shows up. When the new guy's lowbrow tactics impinge on his own sophisticated work and believing him to be the infamous conman 'The Jackal', Lawrence resolves to get rid of him. Confident of his own duplicitous talents, he challenges Freddy to a winner-takes-all competition: whoever swindles their latest mark, American heiress Janet Colgate, out of $50,000 first can stay, while the other must leave town.
Suicide Kings
Carlo, a former mobster, is abducted by five privileged young men desperate to raise a $2 million ransom to save the sister of a friend. As Carlo plays mind games, however, his captors splinter -- each wondering whether one of their own had a hand in the crime.
Dirty Work
Unemployed and recently dumped, Mitch and his buddy Sam start a revenge-for-hire business to raise the $50,000 that Sam's father needs to get a heart transplant.
The Odd Couple
In New York, Felix, a neurotic news writer who just broke up with his wife, is urged by his chaotic friend Oscar, a sports journalist, to move in with him, but their lifestyles are as different as night and day are, so Felix's ideas about housekeeping soon begin to irritate Oscar.
Get Shorty
Chili Palmer is a Miami mobster who gets sent to L.A. to collect a bad debt from Harry Zimm, a Hollywood producer who specializes in cheesy horror films. When Chili meets Harry's leading lady, the romantic sparks fly. After pitching his own life story as a movie idea, Chili learns that being a mobster and being a Hollywood producer really aren't all that different.
Think Like a Man Too
All the couples are back for a wedding in Las Vegas, but plans for a romantic weekend go awry when their various misadventures get them into some compromising situations that threaten to derail the big event.
29th Street
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.
Greedy
Meet the McTeagues. They've come to stake a claim in their wealthy uncle's will… only he's not dead yet!
3000 Miles to Graceland
It was an ingenious enough plan: rob the Riviera Casino's count room during an Elvis impersonator convention. But Thomas Murphy decided to keep all the money for himself and shot all his partners, including recently-freed ex-con Michael Zane. With $3.2 million at stake, the Marshals Service closing in, Michael must track down Murphy.
Ghosts of Girlfriends Past
Celebrity photographer Connor Mead lives life in the fast lane, committed to lifelong bachelorhood and simultaneous relationships with multiple women. On the eve of his younger brother Paul's wedding, Connor's mockery of love proves a real buzz-kill for everyone - including his childhood crush, Jenny, the one woman who always seemed immune to his considerable charms. Later that night, he gets a wake-up call from the ghost of his late Uncle Wayne, the hard-partying, legendary ladies' man who was Connor's mentor. Uncle Wayne has an urgent message which he delivers through three ghosts who guide Connor on an eye-opening tour of his romantic past, present and future. Along the way, they attempt to discern whether he will ever be able to change his ways -- and if there is any hope of him finding true love.
Quiz Lady
A brilliant but tightly wound, gameshow-obsessed young woman, Anne, and her estranged, train-wreck of a sister, Jenny, must work together to help cover their mother's gambling debts. When Anne's beloved dog is kidnapped, they set out on a wild, cross-country trek to get the cash the only way they know how: by turning Anne into a bona-fide gameshow champion.
Why These Movies Are Similar
These recommendations share core qualities with Win It All (2017): Comedy themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of Win It All.
See full details for Win It All (2017)