Movies Like When We Were Twenty-One

If you liked When We Were Twenty-One (1921), a comedy and drama movie directed by Henry King, 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
Don't Think Twice (2016)
★ 6.4/10Also comedy and drama
An improv group deals with several crises, including the loss of their lease and one member hitting the big time.
2
Class Act (1992)
★ 6.3/10Also comedy and drama
Duncan is a genius straight A student, Blade is ajuvenile delinquent. But because of a mix up with their school records, everyone thinks each is the other one. Now, Duncan kind of likes the attention from being thought…
3
It Runs in the Family (2003)
★ 6/10Also comedy and drama
This is the story of a dysfunctional New York family, and their attempts to reconcile
4
Best Man Down (2012)
★ 6.6/10Also comedy and drama
A newlywed couple cancels their honeymoon and returns to the snowy Midwest to make the funeral arrangements for their best man, who died unexpectedly after their ceremony.
5
The Good Half (2024)
★ 6.2/10Also comedy and drama
Renn Wheeland returns home to Cleveland for his mother's funeral. Once there, he forges new relationships while healing old ones, before confronting his problems and trying to face his grief.
6
Feel the Beat (2020)
★ 7.5/10Also comedy and drama
After failing to make it on Broadway, April returns to her hometown and reluctantly begins training a misfit group of young dancers for a competition.
7
Wild Oats (2016)
★ 6.1/10Also comedy and drama
Everything changes for Eva when she receives an insurance settlement check accidentally made out for $5,000,000 instead of the expected $50,000. She and her best friend take the money and head out for the adventure of…
8
Better Living Through Chemistry (2014)
★ 5.9/10Also drama and comedy
A straight-laced pharmacist's uneventful life spirals out of control when he starts an affair with a trophy wife customer who takes him on a joyride involving sex, drugs and possibly murder.
9
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…
10
Hard Sell (2016)
★ 5.9/10Also comedy and drama
Senior Hardy Buchanan struggles to keep up at an elite private school while caring for his unstable mother and raising money for surgery to save their beloved family dog. Desperate for cash, he teams up with a…
11
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.
12
Sometimes Always Never (2019)
★ 6.4/10Also drama and comedy
Alan is a stylish tailor with moves as sharp as his suits. He has spent years searching tirelessly for his missing son Michael who stormed out over a game of Scrabble. With a body to identify and his family torn apart…
13
Afterlife of the Party (2021)
★ 6.7/10Also comedy and drama
A social butterfly who dies during her birthday week is given a second chance to right her wrongs on Earth.
14
Swimming with Men (2018)
★ 6/10Also comedy and drama
A man who is suffering a mid-life crisis finds new meaning in his life as part of an all-male, middle-aged, amateur synchronised swimming team.
15
Gabriel Iglesias: Aloha Fluffy (2013)
★ 7.1/10Also comedy
ALOHAAAAA! Internationally acclaimed comedian, Gabriel Iglesias, returns to Comedy Central with his latest stand-up special taped at Honolulu’s Hawaii Theatre Center. Watch as Fluffy brings the house down yet again in…
16
Chang Can Dunk (2023)
★ 6.7/10Also comedy and drama
Chang, a 16-year-old, Asian American, bets the high school basketball star that he can dunk by Homecoming. The bet leads 5' 8" Chang on a quest to learn to dunk—not only to impress his crush, Kristy, but to gain the…
17
Uptown Girls (2003)
★ 7.1/10Also comedy and drama
Molly Gunn, the freewheeling daughter of a deceased rock legend, is forced to get a job when her manager steals her money. As nanny to Ray - the precocious, oft-ignored daughter of a music executive - she learns what…
18
A Flintstones Christmas Carol (1994)
★ 6.8/10Also comedy
Fred is cast as Ebenezer Scrooge in a stage adaption of the classic Christmas story, but is acting a bit stingy in real life.
19
The Happiest Millionaire (1967)
★ 6.8/10Also comedy and drama
A happy and unbelievably lucky young Irish immigrant, John Lawless, lands a job as the butler of an unconventional millionaire, Biddle. His daughter, Cordelia Drexel Biddle, tires of the unusual antics of her…
20
Song of the Thin Man (1947)
★ 6.7/10Also comedy
While attending a glamorous jazz cruise on New York’s East River, Nick and Nora Charles witness the fatal shooting of a wealthy patron. When suspicion falls on a young bandleader and his musicians, the couple steps in…