Movies Like Chartroose Caboose

If you liked Chartroose Caboose (1960), a comedy and music movie directed by William 'Red' Reynolds, 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
A Song Is Born (1948)
★ 6.5/10Also comedy and music
The story of seven scholars in search of an expert to teach them about swing music. They seem to have found the perfect candidate in winsome nightclub singer Honey Swanson. But Honey's gangster boyfriend doesn't want…
2
Babes in Arms (1939)
★ 6.4/10Also comedy and music
Mickey Moran, son of two vaudeville veterans, decides to put up his own vaudeville show with his girlfriend Patsy Barton. But child actress Rosalie wants to make a comeback and replace Patsy both professionally and as…
3
Love Happy (1949)
★ 5.8/10Also comedy and music
The Marx Brothers help young Broadway hopefuls when they get mixed up with gangsters due to a tin of sardines containing Romanoff diamonds.
4
Footlight Parade (1933)
★ 6.8/10Also comedy and music
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.
5
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.
6
A Day at the Races (1937)
★ 7.1/10Also comedy and music
Doctor Hugo Hackenbush, Tony, and Stuffy try and save Judy's sanitarium by winning a big race with a finicky horse owned by Judy's boyfriend Gil. There are a few problems. Hackenbush, who was recently put in charge of…
7
The Big Store (1941)
★ 6.3/10Also comedy and music
A detective is hired to protect the life of a singer, who has recently inherited a department store, from the store's crooked manager.
8
Wayne's World (1992)
★ 6.7/10Also comedy and music
The adventures of two amiably aimless metal-head friends, Wayne and Garth. From Wayne's basement, the pair broadcast a talk-show called "Wayne's World" on local public access television. The show comes to the attention…
9
CB4 (1993)
★ 6.1/10Also comedy and music
A "rockumentary", covering the rise to fame of MC Gusto, Stab Master Arson, and Dead Mike: members of the rap group "CB4". We soon learn that these three are not what they seem and don't appear to know as much about…
10
The Girl Can't Help It (1956)
★ 6.3/10Also comedy and music
A down-and-out gangster hires a down-on-his-luck agent to make his girlfriend a recording star within six weeks.
11
The Rocker (2008)
★ 6.1/10Also comedy and music
In the 1980s, a drummer is abandoned by his band just before they become rock superstars. Twenty years later, the drummer sees his second chance at stardom arise when he is asked to perform with his teenage nephew's…
12
Playing with Fire (2019)
★ 6.6/10Also comedy
A crew of rugged firefighters meet their match when attempting to rescue three rambunctious kids.
13
My Little Pony: Best Gift Ever (2018)
★ 7.5/10Also comedy and music
As the ponies prepare for another Hearth's Warming, families come together to celebrate the holiday; Pinkie Pie, Fluttershy, Applejack, Rarity, and Rainbow Dash are ready for the big day, but Princess Twilight Sparkle…
14
Sneakerella (2022)
★ 5.9/10Also music and comedy
When El, an aspiring sneaker designer from Queens, meets Kira King, the fiercely independent daughter of legendary basketball star and sneaker tycoon Darius King, sparks fly as the two bond over their mutual affinity…
15
Animal Crackers (1930)
★ 6.9/10Also comedy and music
The well-known explorer and hunter Captain Spaulding has just returned from Africa, and is being welcomed home with a lavish party at the estate of influential society matron Mrs. Rittenhouse when a valuable painting…
16
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…
17
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.
18
Paint Your Wagon (1969)
★ 6.3/10Also comedy and music
A Michigan farmer and a prospector form a partnership in the California gold country. Their adventures include buying and sharing a wife, hijacking a stage, kidnapping six prostitutes, and turning their mining camp…
19
The Ladies Man (1961)
★ 6.3/10Also comedy
After his girl leaves him for someone else, Herbert gets really depressed and starts searching for a job. He finally finds one in a big house which is inhabited by many, many women. Can he live in the same home with…
20
Mixtape (2021)
★ 6.9/10Also comedy
On the eve of Y2K, orphaned 12-year-old Beverly discovers a broken mixtape crafted by her teen parents. Raised by her grandmother – who struggles talking about her late daughter – Beverly sees the mixtape as a chance…