Movies Like Winners & Losers

If you liked Winners & Losers, a movie directed by Cecelia Wheeler, 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
Two for the Money (2005)
★ 6.1/10
A former college athlete joins forces with a sports consultant to handicap football games for high-rolling gamblers.
2
Duplex (2003)
★ 6.1/10
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
3
Hardball (2001)
★ 6.5/10
An aimless young man who is scalping tickets, gambling and drinking, agrees to coach a Little League team from the Cabrini Green housing project in Chicago as a condition of getting a loan from a friend.
4
Pillow Talk (1959)
★ 7.1/10
Playboy songwriter Brad Allen's succession of romances annoys his neighbor, interior designer Jan Morrow, who shares a telephone party line with him and hears all his breezy routines. After Jan unsuccessfully lodges a…
5
Good Neighbor Sam (1964)
★ 6.6/10
To help his divorced neighbor claim a substantial inheritance, a family man poses as her husband. The ruse spills over into his career in advertising, and his recent promotion relies on his wholesome and moral…
6
How to Lose a Guy in 10 Days (2003)
★ 6.9/10
It's the battle of wills, as Andie needs to prove she can dump a guy in 10 days, whereas Ben needs to prove he can win a girl in 10 days. Now, the clock is ticking—and the wildly entertaining comedy smash is off and…
7
A Bride for Christmas (2012)
★ 6.3/10
Bride-to-be Jessie Patterson calls off her third engagement - during the ceremony! She swears off serious relationships, until she meets and is pursued by Aiden MacTiernan. Aiden, on the other hand, has bet his friends…
8
Trading Places (1983)
★ 7.2/10
A snobbish investor and a wily street con-artist find their positions reversed as part of a bet by two callous millionaires.
9
Fast Girls (2012)
★ 6/10
A street smart runner develops an intense rivalry with an equally ambitious wealthy young athlete.
10
The Choice (2016)
★ 7.2/10
Travis and Gabby first meet as neighbors in a small coastal town and wind up in a relationship that is tested by life's most defining events.
11
Walk on the Wild Side (1962)
★ 6.6/10
At a 1930s New Orleans bordello, Hallie is the main attraction for both clients and the shrewd madam. The arrival of Dove Linkhorn, her lovesick sweetheart from three years ago, disrupts the normal and triggers a chain…
12
Sidelined: The QB and Me (2025)
★ 6.4/10
Dallas, a burdened but headstrong dancer, is determined to get into the best dance school in the country—her late mother’s alma mater. However, that dream is suddenly derailed when the cheeky yet secretly grieving…
13
Goal! (2005)
★ 6.8/10
Like millions of kids around the world, Santiago harbors the dream of being a professional footballer... However, living in the Barrios section of Los Angeles, he thinks it is only that—a dream. Until one day an…
14
Swimming for Gold (2020)
★ 7.5/10
Young elite swimmer Claire is sent to Australia to coach a boys swimming team, where she must overcome an old rival and a secret fear to save the swimming camp from closing.
15
Herself (2020)
★ 6.7/10
Struggling to provide her daughters with a safe, happy home, Sandra decides to build one - from scratch. Using all her ingenuity to make her ambitious dream a reality, Sandra draws together a community to lend a…
16
Little Men (2016)
★ 6.4/10
Jake is a quiet, sensitive middle schooler with dreams of being an artist. He meets the affably brash Tony at his grandfather's funeral, and the unlikely pair soon hit it off. The budding friendship is put at risk…
17
Little Brother (2026)
★ 6.4/10
A tightly wound realtor's picture-perfect life gets an extreme makeover when his lovably chaotic "little brother" suddenly reappears.
18
Some Kind of Wonderful (1987)
★ 6.8/10
Keith Nelson, an artsy high school outcast, tries to land a date with popular girl Amanda Jones with some help from his tomboy best friend, Watts. However, Watts realizes she likes Keith as more than just a friend and…
19
Petulia (1968)
★ 6/10
Dr. Archie Bollen is having a midlife crisis. He's just divorced his wife and is establishing a new life for himself. One night, he catches the eye of Petulia Danner, a charming, free-spirited young woman. Petulia's…
20
The Million Pound Note (1954)
★ 7/10
An impoverished American sailor is fortunate enough to be passing the house of two rich gentlemen who have conceived the crazy idea of distributing a note worth one million pounds. The sailor finds that whenever he…