Movies Like Win, Lose or Love

If you liked Win, Lose or Love (2015), a movie directed by Steven R. Monroe, 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
Donnie Darko (2001)
★ 7.8/10
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 (2019)
★ 7.4/10
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 eventually placed under severe strain by…
3
Last Chance Harvey (2008)
★ 6.3/10
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, Harvey meets Kate, a British…
4
Giant Little Ones (2019)
★ 7.1/10
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 birthday party.
5
Failure to Launch (2006)
★ 5.9/10
At 35, Tripp has an interesting job, a hip car, a passion for sailing, an active dating life, and a great house - trouble is, he still lives with his parents, Al and Sue, who are not happy about it. Al and Sue are…
6
Parents (1989)
★ 5.9/10
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 to suspect his parents are cooking more…
7
Daddy's Home (2015)
★ 6.3/10
The story of a mild-mannered radio executive who strives to become the best stepdad ever to his wife's two children, but complications ensue when their freewheeling, freeloading real father arrives, forcing stepdad to…
8
Dreamer: Inspired By a True Story (2005)
★ 7.1/10
Ben Crane believes that a severely injured racehorse deserves another chance. He and his daughter Cale adopt the mare and save it from being sacrificed by the owner.
9
Remember Me (2010)
★ 7.1/10
Still reeling from a heartbreaking family event and his parents' subsequent divorce, Tyler Hawkins discovers a fresh lease on life when he meets Ally Craig, a gregarious beauty who witnessed her mother's death. But as…
10
A Family Man (2016)
★ 6.7/10
Dane Jensen is a driven, Chicago-based headhunter, working at a cut-throat job placement firm. When his boss pits Dane against Lynn Vogel, Dane's equally driven but polar-opposite rival at the firm, in a battle for…
11
Daddy Day Care (2003)
★ 5.9/10
Two men get laid off and have to become stay-at-home dads when they can't find jobs, which inspires them to open their own day-care center.
12
Jeepers Creepers 2 (2003)
★ 6.2/10
When their bus is crippled on the side of a deserted road, a team of high school athletes discover an opponent they cannot defeat – and may not survive.
13
You Should Have Left (2020)
★ 6.1/10
In an effort to repair their relationship, a couple books a vacation in the countryside for themselves and their daughter. What starts as a perfect retreat begins to fall apart as one loses their grip on reality, and a…
14
The Kindness of Strangers (2019)
★ 6.4/10
Clara and her two sons escape from her abusive husband with little more than their car and plan to start over in New York. After the car towed away, the family meets Alice, who gets them into an emergency shelter…
15
Brothers of the Wind (2015)
★ 7.1/10
The way of the eagle is to raise two chicks. The stronger is destined always to throw the weaker from the nest. Man also has his ways, often to hurt those closest to him. Lukas suffers at the hands of a father who has…
16
Parenthood (1989)
★ 6.7/10
The story of the Buckman family and friends, attempting to bring up their children. They suffer/enjoy all the events that occur: estranged relatives, the 'black sheep' of the family, the eccentrics, the skeletons in…
17
The Land Before Time X: The Great Longneck Migration (2003)
★ 6.3/10
A bedtime story leads Littlefoot and his grandparents on a journey to a new land, where Littlefoot discovers someone who vanished before he was born: his father! Now Littlefoot must decide between two worlds. Will he…
18
Radio Flyer (1992)
★ 7.1/10
A father reminisces about his childhood when he and his younger brother moved to a new town with their mother, her new husband and their dog, Shane. When the younger brother is subjected to physical abuse at the hands…
19
Camp Nowhere (1994)
★ 6/10
Morris "Mud" Himmel has a problem. His parents desperately want to send him away to summer camp. He hates going to summer camp, and would do anything to get out of it. Talking to his friends, he realizes that they are…
20
Captain Fantastic (2016)
★ 7.9/10
Deep in the forests of the Pacific Northwest, a father devoted to raising his six kids with a rigorous physical and intellectual education is forced to leave his paradise and enter the world, beginning a journey that…