Movies Like The Strolling '20s

If you liked The Strolling '20s (1966), a music and comedy movie directed by Charles S. Dubin, 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
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy and tv movie
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
2
Godspell (1973)
★ 6.7/10Also comedy and music
In modern-day New York City, John the Baptist calls out to a group of young men and women to learn from the teachings of Jesus. Through song and dance, they relive Christ's crucifixion.
3
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedy and tv movie
In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.
4
The Muppet Show (2026)
★ 7.2/10Also comedy and music
Music, comedy, and a whole lot of chaos is bound to ensue when The Muppets once again take the stage of the original Muppet Theatre with their very special guest, Sabrina Carpenter!
5
The Rutles: All You Need Is Cash (1978)
★ 6.8/10Also comedy and music
The story of the rise and fall of the Pre-Fab Four.
6
iParty with Victorious (2011)
★ 7.3/10Also comedy and music
Scorned girlfriends Carly and Tori hatch a plot against the boy that they are both dating.
7
Ziegfeld Follies (1945)
★ 6/10Also music and comedy
The late, great impresario Florenz Ziegfeld looks down from heaven and ordains a new revue in his grand old style.
8
Gabriel Iglesias: Hot and Fluffy (2007)
★ 7.6/10Also comedy and tv movie
Gabriel Iglesias is one of the fastest-rising comics today! With his unique brand of humor, lovable stage presence and wide range of voices and impressions, it's no wonder that he already has a huge fan following. Now…
9
Kevin James: Never Don't Give Up (2018)
★ 6.2/10Also comedy and tv movie
Kevin James makes his long-awaited return to stand-up in this family-friendly special, dishing on fatherhood, fans, his disdain for allergies and more.
10
The Wizards Return: Alex vs. Alex (2013)
★ 7.8/10Also comedy and tv movie
While trying to prove to her family she can be mature and responsible, teen wizard Alex Russo conjures up a spell to rid herself of her bad qualities, unintentionally creating a Good and Evil Alex. When Evil Alex gets…
11
Dolly Parton's Christmas on the Square (2020)
★ 5.9/10Also comedy and music
A rich and nasty woman returns to her hometown to evict everyone but discovers the true meaning of Christmas thanks to the local townsfolk – and an actual angel. Features 14 original songs with music and lyrics by…
12
Bo Burnham: Make Happy (2016)
★ 8/10Also comedy and music
Combining his trademark wit and self-deprecating humor with original music, Bo Burnham offers up his unique twist on life in this stand-up special about life, death, sexuality, hypocrisy, mental illness and Pringles…
13
Psych: The Movie (2017)
★ 7.2/10Also comedy and tv movie
The ambitious friends come together during the holidays after a mystery assailant targets one of their own. A comedic thrill-ride follows, as the wild and unpredictable Psych team pursues the bad guys, justice … and…
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
Demetri Martin: The Overthinker (2018)
★ 6.8/10Also comedy and tv movie
With his signature one-liners and drawings, Demetri Martin muses on doughnut holes, dogs, sports bars, the alphabet's most aggressive letters and more.
16
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…
17
Better Nate Than Ever (2022)
★ 6.5/10Also music and comedy
13-year-old Nate Foster has big Broadway dreams but there’s only one problem — he can’t even land a part in the school play. When his parents leave town, Nate and his best friend Libby sneak off to the Big Apple for a…
18
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…
19
Ricky Gervais: Mortality (2025)
★ 7/10Also comedy and tv movie
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
20
Gabriel Iglesias: Aloha Fluffy (2013)
★ 7.1/10Also comedy and tv movie
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…