Movies Like Little Orphan Annie

If you liked Little Orphan Annie (1932), a comedy movie directed by John S. Robertson, 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
Chestnut: Hero of Central Park (2004)
★ 7.3/10Also comedy
Ray and Sal, two orphaned sisters, adopt and hide a Great Dane puppy from their two adopted parents living in a luxury downtown New York apartment that expressely forbids dogs.
2
The Three Stooges (2012)
★ 5.8/10Also comedy
Left on the doorstep of an orphanage run by nuns, three newborn knuckleheads grow up to be finger-poking, nyuk-nyuking janitors named Larry, Curly and Moe. When they learn that financial problems will soon force the…
3
Hotel for Dogs (2009)
★ 6.1/10Also comedy
Placed in a foster home that doesn't allow pets, 16-year-old Andi and her younger brother, Bruce, turn an abandoned hotel into a home for their dog. Soon other strays arrive, and the hotel becomes a haven for every…
4
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10Also comedy
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
5
Beverly Hills Chihuahua 2 (2011)
★ 5.9/10Also comedy
Puppy mayhem turns the lives of newlywed Chihuahua parents Papi and Chloe upside down when their rambunctious, mischievous puppies present one challenge after another. But when their human owners end up in trouble, the…
6
Little Man (2006)
★ 5.9/10Also comedy
After leaving prison, dwarf criminal Calvin Sims joins his moron brother Percy in stealing an expensive huge diamond from a jewelry store for the mobster Walken. They are chased by the police, and Calvin hides the…
7
Sextuplets (2019)
★ 6.2/10Also comedy
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
8
Thunderstruck (2012)
★ 6.2/10Also comedy
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
9
Curly Top (1935)
★ 6.5/10Also comedy
Wealthy Edward Morgan becomes charmed with a curly-haired orphan and her pretty older sister Mary and arranges to adopt both under the alias of "Mr. Jones". As he spends more time with them, he soon finds himself…
10
St. Vincent (2014)
★ 7.1/10Also comedy
A young boy whose parents just divorced finds an unlikely friend and mentor in the misanthropic, bawdy, hedonistic, war veteran who lives next door.
11
Annie (1999)
★ 6.5/10Also comedy
Things seem pretty bad for a young girl living a "hard-knock life" in an orphanage. Fed up with the dastardly Miss Hannigan, Annie escapes the run-down orphanage determined to find her mom and dad. It's an adventure…
12
Problem Child (1990)
★ 6.2/10Also comedy
Ben Healy and his social climbing wife Flo adopt fun-loving seven year old Junior. But they soon discover he's a little monster as he turns a camping trip, a birthday party and even a baseball game into comic nightmares.
13
The Super (1991)
★ 5.9/10Also comedy
Louie Kritski is a heartless landlord who has been so negligent in keeping up his ghetto apartment that he is threatened with jail time. The judge gives him another option -- he must live in his rat-infested hell hole…
14
Firehouse Dog (2007)
★ 6.2/10Also comedy
Rexxx, Hollywood's top canine star, gets lost and is adopted into a shabby firehouse. He teams up with a young kid to get the station back on its feet.
15
3 Men and a Baby (1987)
★ 6.2/10Also comedy
Three bachelors find themselves forced to take care of a baby left by one of the guy's girlfriends.
16
Rookie of the Year (1993)
★ 6.2/10Also comedy
When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.
17
Joy Ride (2023)
★ 6.5/10Also comedy
When Audrey's business trip to Asia goes sideways, she enlists the aid of Lolo, her irreverent, childhood best friend who also happens to be a hot mess; Kat, her college friend turned Chinese soap star; and Deadeye…
18
Spa Weekend (2026)
★ 6.5/10Also comedy
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…
19
Little Big League (1994)
★ 6/10Also comedy
When the owner of the Minnesota Twins passes away, he bequeaths the team to his preteen grandson. The newly minted head honcho quickly appoints himself manager, causing unrest in an organization that struggles to take…
20
Pretty Persuasion (2005)
★ 5.8/10Also comedy
A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.