Movies Like Delivering Milo

If you liked Delivering Milo (2001), a comedy and drama movie directed by Nick Castle, 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
Good Fortune (2025)
★ 6.9/10Also comedy and fantasy
A well-meaning but rather inept angel named Gabriel meddles in the lives of a struggling gig worker and a wealthy capitalist.
2
How Sarah Got Her Wings (2015)
★ 5.9/10Also drama and fantasy
Good Samaritan Sarah Fitzpatrick has a fatal accident just before Christmas, and finds herself in the lobby before the gates of Heaven. Certain that she will be let in, she is shocked to find that her name is not on…
3
Northfork (2003)
★ 6/10Also fantasy and drama
The year is 1955, and a great flood is coming to Northfork, Montana. A new hydroelectric dam is about to be installed in the mountains above the town, ready to submerge the valley in the name of progress. It is the…
4
A Thousand Words (2012)
★ 6.1/10Also drama and comedy
Jack McCall is a fast-talking literary agent, who can close any deal, any time, any way. He has set his sights on New Age guru Dr. Sinja for his own selfish purposes. But Dr. Sinja is on to him, and Jack’s life comes…
5
My Own Love Song (2010)
★ 6.2/10Also comedy and drama
A wheelchair-bound singer and her best friend embark on a roadtrip to Memphis.
6
The Shepherd (2023)
★ 7/10Also drama and fantasy
On Christmas Eve, a fighter pilot on his way home becomes lost while flying over water and needs a miracle to land safely.
7
Candy Cane Lane (2023)
★ 6/10Also comedy and fantasy
Determined to win the neighborhood's annual Christmas decorating contest, family man Chris makes a pact with an elf to help him out-do the competition. However, the elf casts a spell bringing the twelve days of…
8
The Spitfire Grill (1996)
★ 6.5/10Also comedy and drama
Percy, upon being released from prison, goes to the small town of Gillead, to find a place where she can start over again. She is taken in by Hannah, to help out at her place, the Spitfire Grill. Percy brings change to…
9
The Good Witch (2008)
★ 7.1/10Also fantasy and drama
A mysterious woman comes in to town and inhabits the local haunted mansion, making everyone wonder if she's a witch or "The Grey Lady".
10
Dead Like Me: Life After Death (2009)
★ 6.4/10Also drama and fantasy
When George and her colleagues get a new boss whose focus is on moving souls quickly and enjoying life without consequences, the team begins to break the strict reaper rules. While her friends fall victim to their…
11
It's a Wonderful Life (1946)
★ 8.3/10Also drama and fantasy
George Bailey has spent his entire life giving to the people of Bedford Falls. All that prevents rich skinflint Mr. Potter from taking over the entire town is George's modest building and loan company. But on Christmas…
12
Ladyhawke (1985)
★ 7/10Also comedy and fantasy
Captain Etienne Navarre is a man on whose shoulders lies a cruel curse. Punished for loving each other, Navarre must become a wolf by night whilst his lover, Lady Isabeau, takes the form of a hawk by day. Together…
13
Chloe and Theo (2015)
★ 5.9/10Also comedy and drama
A young woman, Chloe, living by her wits on the streets of New York City, has a chance meeting with a wise Inuit Eskimo, Theo, who was sent to New York by his elders to provide a message to the people of the world – We…
14
Guarding Tess (1994)
★ 6/10Also comedy and drama
Doug is a Secret Service Agent who has just completed his stint in charge protecting Tess Carlisle—the widow of a former U.S. President, and a close personal friend of the current President. He finds that she has…
15
My Babysitter's a Vampire (2010)
★ 7.1/10Also comedy and fantasy
Geeky 14-year old Ethan is left to babysit his younger sister, Jane, with his best friend Benny but after Ethan inadvertently puts Jane in harm's way, his parents hire a professional babysitter, the beautiful yet…
16
The Warriors Gate (2016)
★ 6.6/10Also comedy and fantasy
After a mysterious chest opens a gateway through time, teen gamer Jack is transported to an ancient empire terrorized by a cruel barbarian king. Jack will need all of his gaming skills as he battles to defeat the…
17
Young Adult (2011)
★ 5.8/10Also comedy and drama
A divorced writer from the Midwest returns to her hometown to reconnect with an old flame, who's now married with a family.
18
Shorts (2009)
★ 5.9/10Also fantasy and comedy
A young boy's discovery of a colorful, wish-granting rock causes chaos in the suburban town of Black Falls when jealous kids and scheming adults alike set out to get their hands on it.
19
Vampire Academy (2014)
★ 6.3/10Also comedy and fantasy
Rose, a rebellious half-vampire/half-human guardian-in-training and her best friend, Lissa -- a mortal, royal vampire Princess - have been on the run when they are captured and returned to St. Vladamirs Academy, the…
20
Switch (1991)
★ 5.9/10Also fantasy and comedy
Steve Brooks, a sexist womanizer, is killed by a group of his angry former lovers. In heaven, he makes a bargain with God for redemption and agrees to return to Earth. Once there, he must have a sincere relationship…