Movies Like Mississippi Grind

If you liked Mississippi Grind (2015), a comedy and drama movie directed by Anna Boden and Ryan Fleck, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Maverick (1994)
★ 6.9/10Also comedy and drama
Bret Maverick is a gambler who would rather con someone than fight them, and needs an additional $3k in order to enter a winner-takes-all poker game beginning in a few days. He joins forces with a woman with a…
2
Rat Race (2001)
★ 6.3/10Also comedy
In an ensemble film about easy money, greed, manipulation and bad driving, a Las Vegas casino tycoon entertains his wealthiest high rollers -- a group that will bet on anything -- by pitting six ordinary people against…
3
21 (2008)
★ 6.7/10Also drama
Ben Campbell is a young, highly intelligent student at M.I.T. who strives to succeed. Wanting a scholarship to transfer to Harvard School of Medicine to become a doctor, Ben learns that he cannot afford the $300,000…
4
Dinner Rush (2000)
★ 7/10Also drama
One unlucky evening, Louis Cropa, a part-time bookmaker, discovers that his restaurant has become a hotbed of conflicting characters. In addition to having to please a whiny food critic, Louis must fend off a hostile…
5
My One and Only (2009)
★ 6.6/10Also comedy and drama
A mother takes her two sons on an unusual road trip from New York to Pittsburgh, St. Louis and eventually Hollywood in her quest to find a man to take care of them all.
6
Half Brothers (2020)
★ 7.2/10Also comedy and drama
Mexican aviation exec Renato is shocked to learn that he has an American half-brother he never knew about: free-spirited Asher. They are forced on a road trip together, tracing the path their father took from Mexico to…
7
Poolhall Junkies (2002)
★ 6.4/10Also comedy and drama
A retired pool hustler is forced to pick up the stick again when his brother starts a game he can't finish.
8
Get Shorty (1995)
★ 6.5/10Also comedy
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…
9
Last Holiday (2006)
★ 7.3/10Also comedy and drama
The discovery that she has a terminal illness prompts introverted department store saleswoman Georgia Byrd to reflect on what she realizes has been an overly cautious life. With weeks to live, she withdraws her life…
10
Stranger Than Paradise (1984)
★ 7.1/10Also comedy and drama
New York layabout Willie forms an unexpected bond with his young Hungarian cousin Eva when she pays him a surprise visit. Later, Eva moves in with their aunt in Cleveland, and Willie takes his best friend Eddie to see…
11
Young Adult (2011)
★ 5.8/10Also comedy and drama
A divorced writer from the Midwest returns to her hometown to reconnect with an old flame, who's now married with a family.
12
Owning Mahowny (2003)
★ 6.8/10Also drama
Dan Mahowny was a rising star at the Canadian Imperial Bank of Commerce. At twenty-four he was assistant manager of a major branch in the heart of Toronto's financial district. To his colleagues he was a workaholic. To…
13
Lost in America (1985)
★ 6.9/10Also comedy
David and Linda Howard are successful yuppies from LA. When he gets a job disappointment, David convinces Linda that they should quit their jobs, liquidate their assets, and emulate the movie Easy Rider, spending the…
14
Ride Along 2 (2016)
★ 6.3/10Also comedy
As his wedding day approaches, Ben heads to Miami with his soon-to-be brother-in-law James to bring down a drug dealer who's supplying the dealers of Atlanta with product.
15
Ana (2020)
★ 6.3/10Also drama and comedy
Ana meets Rafa in a chance encounter and they embark on a road trip to try and save him from bankruptcy, or worse.
16
A Man Called Otto (2022)
★ 7.7/10Also comedy and drama
When a lively young family moves in next door, grumpy widower Otto Anderson meets his match in a quick-witted, pregnant woman named Marisol, leading to an unlikely friendship that turns his world upside down.
17
Family Plot (1976)
★ 6.8/10Also comedy
Spiritualist Blanche Tyler and her cab-driving boyfriend encounter a pair of serial kidnappers while trailing a missing heir in California.
18
Little Miss Sunshine (2006)
★ 7.7/10Also comedy and drama
A family loaded with quirky, colorful characters piles into an old van and road trips to California for little Olive to compete in a beauty pageant.
19
Nightmare Alley (1947)
★ 7.2/10Also drama
A roustabout joins a traveling carny and schemes to figure out the mind-reading act of Mademoiselle Zeena and her alcoholic husband.
20
Easy Money (1983)
★ 6/10Also comedy
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.