Dynamic Watchlist Hub: Apr 20, 2026

10 Best Movies Like Win, Lose or Love

If you loved Win, Lose or Love, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

🏆

Expert Review & Ratings

See our full critical analysis and audience score for Win, Lose or Love.

View Review →
Advertisement
#1
Donnie Darko

Donnie Darko

2001★ 7.8

Why watch this? A perfect follow-up to Win, Lose or Love for fans of Fantasy. It captures a similar emotionally gripping atmosphere.

After narrowly escaping a bizarre accident, a troubled teenager is plagued by visions of a large bunny rabbit that manipulates him to commit a series of crimes....

#2
Waves

Waves

2019★ 7.4

Why watch this? A perfect follow-up to Win, Lose or Love for fans of Romance. It captures a similar emotionally gripping atmosphere.

A controlling father’s attempts to ensure that his two children succeed in high school backfire after his son experiences a career-ending sports injury. Their familial bonds are ev...

#3
Kicking & Screaming

Kicking & Screaming

2005★ 5.8

Why watch this? A perfect follow-up to Win, Lose or Love for fans of Family. It captures a similar light-hearted atmosphere.

Phil Weston has been unathletic his entire life. In college he failed at every sport that he tried out for. It looks like his 10-year old son, Sam, is following in his footsteps. B...

#4
Giant Little Ones

Giant Little Ones

2019★ 7.1

Why watch this? A perfect follow-up to Win, Lose or Love for fans of Drama. It captures a similar emotionally gripping atmosphere.

Two popular teen boys, best friends since childhood, discover their lives, families, and girlfriends dramatically upended after an unexpected incident occurs on the night of a 17th...

#5
Last Chance Harvey

Last Chance Harvey

2008★ 6.3

Why watch this? A perfect follow-up to Win, Lose or Love for fans of Drama. It captures a similar emotionally gripping atmosphere.

In London for his daughter's wedding, a struggling jingle-writer, Harvey Shine, misses his plane to New York, and thus loses his job. While drowning his sorrows in the airport pub,...

#6
Parents

Parents

1989★ 5.9

Why watch this? A perfect follow-up to Win, Lose or Love for fans of Horror. It captures a similar spine-chilling atmosphere.

Michael is a young boy living in a typical 1950s suburbanite home... except for his bizarre and horrific nightmares, and continued unease around his parents. Young Michael begins t...

Advertisement