Movies Like Where Milo Used to Sleep

If you liked Where Milo Used to Sleep (2025), a drama movie directed by Fernando Hoswary, 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
A Street Cat Named Bob (2016)
★ 7.9/10Also drama
James Bowen, a homeless busker and recovering drug addict, has his life transformed when he meets a stray ginger cat.
2
The Young One (1960)
★ 7/10Also drama
A jazz musician seeks refuge from a lynch mob on a remote island, where he meets a hostile game warden and the young object of his attentions.
3
Rogue Agent (2022)
★ 6.3/10Also drama
Conman Robert Freegard poses as an undercover MI5 agent and kidnaps countless victims amidst a high-stakes manhunt, until the woman who fell for him brings him to justice.
4
Eleanor the Great (2025)
★ 6.8/10Also drama
94-year-old Eleanor Morgenstein tries to rebuild her life after the death of her best friend. As a result, she moves back to New York City after living in Florida for decades.
5
TalhotBlond (2012)
★ 6.3/10Also drama
Thomas Montgomery, a married father of two young daughters, gets seduced by the world of online gambling and chat rooms where a virtual romance and sexual obsession ultimately leads to the murder of an innocent man.
6
Charm City Kings (2020)
★ 7.8/10Also drama
Mouse desperately wants to join The Midnight Clique, the infamous Baltimore dirt bike riders who rule the summertime streets. When Midnight’s leader, Blax, takes 14-year-old Mouse under his wing, Mouse soon finds…
7
Penguin Bloom (2021)
★ 6.9/10Also drama
When an unlikely ally enters the Bloom family's world in the form of an injured baby magpie they name Penguin, the bird’s arrival makes a profound difference in the struggling family’s life.
8
Pimp (2018)
★ 6.2/10Also drama
An urban love story set on the hard streets of the Bronx. A struggling female pimp, named Wednesday, grows up learning the game from her dad. Once he's gone she's left to look out for her prostitute mother and…
9
The Girl in the Book (2015)
★ 5.8/10Also drama
The story of a young writer's transformation when her past invades her present.
10
Cardboard Boxer (2016)
★ 6.5/10Also drama
Gentle and broken, a homeless man fights others on video for money but soon finds comfort in an unlikely friend and the lost diary of a young girl.
11
The Congress (2013)
★ 6.4/10Also drama
An aging, out-of-work actress accepts one last job, though the consequences of her decision affect her in ways she didn't consider.
12
Lucky Them (2013)
★ 6/10Also drama
More interested in partying and flirting with young musicians than work, veteran rock journalist Ellie Klug has one last chance to prove her value to her magazine’s editor: a no-stone-unturned search to discover what…
13
A Mouthful of Air (2021)
★ 6.4/10Also drama
Julie is a new mom and children's book author, who escapes into the bright Crayola-colored world of her creation in order to leave behind the darkness caused by her post-partum depression.
14
Jane Got a Gun (2015)
★ 5.9/10Also drama
After her outlaw husband returns home shot with eight bullets and barely alive, Jane reluctantly reaches out to an ex-lover who she hasn't seen in over ten years to help her defend her farm when the time comes that her…
15
O.G. (2018)
★ 5.9/10Also drama
Louis Menkins is five weeks away from being released after 26 years in prison. He is faced with the decision to put his own release at risk in order to protect a young man named Beecher from growing gang controversies.
16
The Parts You Lose (2019)
★ 6.7/10Also drama
An unlikely friendship unfolds between a young deaf boy, Wesley, and a fugitive criminal who takes refuge in an abandoned barn on the family’s rural North Dakota farm.
17
The Naked Kiss (1964)
★ 7/10Also drama
A former prostitute works to create a new life for herself in a small town, but a shocking discovery could threaten everything.
18
Home Run (2013)
★ 6.2/10Also drama
A pro ball player with a substance abuse problem is forced into rehab in his hometown, finding new hope when he gets honest about his checkered past, and takes on coaching duties for a misfit Little League team
19
Home (2021)
★ 6.7/10Also drama
An ex-felon returns home from prison and must confront the demons of his past.
20
Where the Red Fern Grows (1974)
★ 6.9/10Also drama
Billy Coleman works hard and saves his earnings for two years to achieve his dream of buying two red-bone coonhound pups. He develops a new trust in life as he faces overwhelming challenges in adventure and tragedy…