Movies Like Hollywood Bound

If you liked Hollywood Bound (1928), a comedy movie directed by Bryan Foy, 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
Room Service (1938)
★ 6.5/10Also comedy
Broke Gordon Miller tries to land a backer for his new play while he has to deal with with the hotel manager trying to evict him and his cast.
2
Taking Care of Business (1990)
★ 6.3/10Also comedy
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
3
The Errand Boy (1961)
★ 6.2/10Also comedy
Paramutual Pictures wants to know where all the money is going so they hire Morty to be their spy. Morty works for Mr. Sneak and gets a job in the mail room so that he can have access to the lot. But all that Morty…
4
Any Old Port! (1932)
★ 7/10Also comedy
Stan and Ollie check into a seedy hotel and help a young girl escape the clutches of the landlord. They are forced to flee the hotel with no money and Ollie arranges for Stan to fight at a local boxing hall for $50…
5
American Dreamer (2022)
★ 6/10Also comedy
In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.
6
Footlight Parade (1933)
★ 6.8/10Also comedy
A fledgling producer finds himself at odds with his workers, financiers and his greedy ex-wife when he tries to produce live musicals for movie-going audiences.
7
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.
8
Jim Jefferies: Freedumb (2016)
★ 7.2/10Also comedy
Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee.
9
Much Ado About Nothing (2013)
★ 6.8/10Also comedy
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
10
Go West (1940)
★ 6.6/10Also comedy
A con man heading west to search for gold teams up with a pair of scheming brothers along the way. The trio soon find themselves in the middle of a feud between two rival families and two underhanded land developers.
11
Good Neighbor Sam (1964)
★ 6.6/10Also comedy
To help his divorced neighbor claim a substantial inheritance, a family man poses as her husband. The ruse spills over into his career in advertising, and his recent promotion relies on his wholesome and moral…
12
Hollywood or Bust (1956)
★ 6.2/10Also comedy
The last movie with Jerry Lewis and Dean Martin together, is a satire of the life in Hollywood. Steve Wiley is a deceiver who cheats Malcolm Smith when he wins a car, claiming that he won it too. Trying to steal the…
13
The Flying Car (2002)
★ 6.7/10Also comedy
Stuck in a traffic jam, Dante and Randal discuss the prospect of a flying car.
14
Bowfinger (1999)
★ 6.2/10Also comedy
On the verge of bankruptcy and desperate for his big break, aspiring filmmaker Bobby Bowfinger concocts a crazy plan to make his ultimate dream movie. Rallying a ragtag team that includes a starry-eyed ingenue, a…
15
Chris Tucker: Live (2015)
★ 6/10Also comedy
Comedian Chris Tucker performs live.
16
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
17
Trailer Park Boys: Don't Legalize It (2014)
★ 6.4/10Also comedy
Out of jail and broke, Julian concocts an outrageously greasy scheme to get rich and, to make it even greasier, he will have to deliver his product to his arch-enemy, Cyrus, who’s waiting in Montreal to close the dirty…
18
Big Fat Liar (2002)
★ 5.9/10Also comedy
After one of his class papers is stolen and turned into a movie, a young student and his best friend exact a hilarious, slapstick revenge on the Hollywood hot shot who has taken credit!
19
The Little Rascals Save the Day (2014)
★ 6.4/10Also comedy
When the Little Rascals are unable to raise enough money to save their grandma's bakery from shutting down, their only hope is to win a local talent show and use the prize money to save the shop.
20
Dog Gone (2008)
★ 6.5/10Also comedy
A courageous boy battles a gang of bumbling thieves to rescue a dog carrying a fortune in stolen diamonds.