Movies Like Dinner with Holly

If you liked Dinner with Holly (2014), a comedy movie directed by Josh Crockett and Daniel Sinclair, 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
The Wedding Year (2019)
★ 5.9/10Also comedy
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
2
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
3
Duplex (2003)
★ 6.1/10Also comedy
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!
4
Mickey's Rival (1936)
★ 6.4/10Also comedy
Minnie's old friend, Mortimer Mouse, drops in on Mickey and Minnie's picnic. His practical jokes and coming on to Minnie soon have Mickey stewing, and their car isn't happy either. When Mortimer gets a nearby bull…
5
Snoopy Presents: Welcome Home, Franklin (2024)
★ 7.7/10Also comedy
Franklin is new to town and hoping to make friends, but his usual tactics don't work on the Peanuts gang. When the Soap Box Derby arrives, he's sure it's a chance to impress new pals and teams up with the only other…
6
Our Wife (1931)
★ 7.1/10Also comedy
Oliver is making plans to marry his sweetheart Dulcy with Stan as his best man, but the plans are thwarted when Dulcy's father sees a picture of Ollie and forbids the marriage. The couple plan to elope, and run away to…
7
The Fixer Uppers (1935)
★ 6.8/10Also comedy
Stan and Ollie are greeting card salesmen who agree to help a woman put a spark in her loveless marriage by making her husband jealous.
8
Rock-a-Bye Baby (1958)
★ 6.9/10Also comedy
An average television repairman must care for the newborn triplets of his former hometown sweetheart—now a famous movie star—so her career will not suffer.
9
Marvel One-Shot: All Hail the King (2014)
★ 6.8/10Also comedy
A documentary filmmaker interviews the now-famous Trevor Slattery from behind bars.
10
Ricky Gervais: Mortality (2025)
★ 7/10Also comedy
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
11
The Flying Car (2002)
★ 6.7/10Also comedy
Stuck in a traffic jam, Dante and Randal discuss the prospect of a flying car.
12
The Hoose-Gow (1929)
★ 6.8/10Also comedy
Stan and Ollie arrive as new inmates at a prison after apparently taking part in a hold-up raid, a raid they tell a prison officer they were only watching. The usual mayhem ensues.
13
Thicker Than Water (1935)
★ 7.4/10Also comedy
Oliver's in trouble with his wife after missing a payment on their furniture, having given the money to Stanley, who used it instead to pay Mrs. Hardy for his room and board. At Stan's suggestion Ollie then withdraws…
14
Red Hot Riding Hood (1943)
★ 7.3/10Also comedy
Tired of always playing the same roles, Little Red Riding Hood, her grandmother and the Wolf demand a new version of the tale. The story then plays out in a more contemporary urban environment, with Little Red Riding…
15
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
16
Caprice (1986)
★ 6.1/10Also comedy
A girl finds herself inside a fashion magazine – Joanna Hogg's graduation piece at the National Film and Television School starring a then unknown Tilda Swinton.
17
Day & Night (2010)
★ 7.7/10Also comedy
When Day, a sunny fellow, encounters Night, a stranger of distinctly darker moods, sparks fly! Day and Night are frightened and suspicious of each other at first, and quickly get off on the wrong foot. But as they…
18
The Overnight (2015)
★ 5.9/10Also comedy
Alex, Emily, and their son, RJ, are new to Los Angeles. A chance meeting at the park introduces them to the mysterious Kurt, Charlotte, and Max. A family “playdate” becomes increasingly interesting as the night goes on.
19
Die, Mommie, Die! (2003)
★ 6.6/10Also comedy
Angela Arden is a washed up, has-been singing star who is trapped in a hateful marriage to film producer Sol Sussman. In an attempt to escape her marriage so that she can be with a hunky layabout, she poisons her…
20
How High (2001)
★ 6.4/10Also comedy
Jamal and Silas, two ordinary guys who smoke something magical, pass their college entrance exams with flying colors and end up at Harvard. Ivy League ways are strange but Silas and Jamal take it in a stride -- until…