Movies Like Pay or Play

If you liked Pay or Play (2007), a movie directed by Sinclair, 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
Milk Money (1994)
★ 6.5/10
Three young boys pool their money and pay V, a kindhearted prostitute, to strip for them. Afterward, she drives them home to the suburbs -- but then her car breaks down. It's just as well, though, because a mobster…
2
Fun with Dick and Jane (1977)
★ 6.6/10
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
3
Adventures in Babysitting (1987)
★ 6.9/10
When plans with her boyfriend fall through, high school senior Chris Parker ends up babysitting the Anderson kids, Brad and Sara. What should be a quiet night in, however, turns into a series of ridiculous exploits…
4
Written on the Wind (1956)
★ 7/10
Mitch Wayne is a geologist working for the Hadleys, an oil-rich Texas family. While the patriarch, Jasper, works hard to establish the family business, his irresponsible son, Kyle, is an alcoholic playboy, and his…
5
Poor Cow (1967)
★ 6.4/10
Joy lives a life filled with bad choices. At a young age, she marries and has a child–with an abusive thief who quickly ends up incarcerated. Left alone, she takes up with the guy's mate, another thief, who seems to…
6
A Night at the Roxbury (1998)
★ 6.6/10
Despite being well into adulthood, brothers Doug and Steve Butabi still live at home and work in the flower shop owned by their dad. They exist only to hit on women at discos, though they're routinely unsuccessful…
7
Step Up All In (2014)
★ 6.8/10
All-stars from previous installments convene in glittering Las Vegas, battling for a victory that could define their dreams and their careers.
8
Bluebeard's Eighth Wife (1938)
★ 7/10
American multi-millionaire Michael Brandon marries his eighth wife, Nicole, the daughter of a broke French Marquis. But she doesn't want to be only a number in the line of his ex-wives and undertakes her own strategy…
9
Scarlet Street (1945)
★ 7.6/10
Cashier and part-time starving artist Christopher Cross is absolutely smitten with the beautiful Kitty March. Kitty plays along, but she's really only interested in Johnny, a two-bit crook. When Kitty and Johnny find…
10
She Done Him Wrong (1933)
★ 5.9/10
New York singer and nightclub owner Lady Lou has more male friends than can be imagined. One is a vicious escaped criminal on the way to see 'his' girl, unaware she hasn't exactly been faithful in his absence. Help is…
11
Don't Tell Mom the Babysitter's Dead (1991)
★ 6.2/10
Sue Ellen Crandell is a teenager eagerly awaiting her mother's summer-long absence. While the babysitter looks after her rambunctious younger siblings, Sue Ellen can party and have fun. But then the babysitter abruptly…
12
The Spy Next Door (2010)
★ 5.9/10
Former CIA spy Bob Ho takes on his toughest assignment to date: looking after his girlfriend's three kids, who haven't exactly warmed to their mom's beau. And when one of the youngsters accidentally downloads a…
13
Easy Virtue (2008)
★ 6.5/10
A young Englishman marries a glamorous American. When he brings her home to meet the parents, she arrives like a blast from the future - blowing their entrenched British stuffiness out the window.
14
King Creole (1958)
★ 6.4/10
Delinquent Danny Fisher flunks out of high school, quits his job as a nightclub busboy, and one night gets the chance to perform. Success is imminent and local crime boss Maxie Fields wants to hire him to perform at…
15
That Touch of Mink (1962)
★ 6.5/10
Cathy Timberlake is en route to a job interview when a car transporting businessman Philip Shayne covers her in mud. He sends his assistant, Roger, to apologize, but upon meeting Cathy, Roger knows that she would be a…
16
A Summer Place (1959)
★ 6.6/10
A self-made businessman rekindles a romance with a former flame while their two teenage children begin a romance of their own with drastic consequences for both couples.
17
The Client List (2010)
★ 5.9/10
After she and her husband lose their jobs, a former Texas homecoming queen inadvertently finds herself in the middle of a prostitution ring after she unknowingly accepts a position at a massage parlor.
18
Return of the Seven (1966)
★ 6.1/10
Chico, one of the remaining members of The Magnificent Seven, now lives in the town that they (The Seven) helped. One day someone comes and takes most of the men prisoner. His wife seeks out Chris, the leader of The…
19
The Bachelor and the Bobby-Soxer (1947)
★ 6.9/10
Teenager Susan Turner, with a severe crush on playboy artist Richard Nugent, sneaks into his apartment to model for him and is found there by her sister Judge Margaret Turner. Threatened with jail, Nugent agrees to…
20
Kitty Foyle (1940)
★ 6.6/10
A hard-working, white-collar girl falls in love with a young socialite, but meets with his family's disapproval.