Movies like The Strolling '20s (1966)
The best movies like The Strolling '20s (1966) are The Rutles: All You Need Is Cash (1978), Steve Martin and Martin Short: An Evening You Will Forget for the Rest of Your Life (2018) and Dolly Parton's Christmas on the Square (2020). If The Strolling '20s hooked you with its music and comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedBo Burnham: Make Happy (2016)8.0/10 from 459 votes
- NewestBill Burr: Drop Dead Years (2025)Released 2025
The Rutles: All You Need Is Cash (1978)
The story of the rise and fall of the Pre-Fab Four.
Why it matches: Recommended by TMDB viewers · both comedy & music
Popcorn FlickMovies like thisSteve Martin and Martin Short: An Evening You Will Forget for the Rest of Your Life (2018)
Comedians and writers Steve Martin and Martin Short perform a live comedy set with music by The Steep Canyon Rangers and jazz pianist, Jeff Babko, at the Peace Center in Greenville, South Carolina.
Why it matches: Recommended by TMDB viewers · both comedy & music
Popcorn FlickMovies like thisDolly Parton's Christmas on the Square (2020)
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 Dolly Parton!
Why it matches: Recommended by TMDB viewers · both comedy & music
SnoozefestMovies like thisJohn Mulaney & The Sack Lunch Bunch (2019)
John Mulaney and his kid pals tackle existential topics for all ages with catchy songs, comedy sketches and special guests in a nostalgic variety special.
Why it matches: Recommended by TMDB viewers · both comedy & music
Worth the HypeMovies like thisZiegfeld Follies (1945)
The late, great impresario Florenz Ziegfeld looks down from heaven and ordains a new revue in his grand old style.
Why it matches: Recommended by TMDB viewers · both music & comedy
Popcorn FlickMovies like thisBill Burr: Drop Dead Years (2025)
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisBo Burnham: Make Happy (2016)
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 cans.
Why it matches: Recommended by TMDB viewers · both comedy & music
Absolute CinemaMovies like thisHow to Irritate People (1969)
A pre-Monty Python mockumentary, written by and presented by John Cleese, that provides tips on learning how to irritate people.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJohn Mulaney: Baby J (2023)
A chaotic intervention. An action-packed stay in rehab. After a weird couple of years, John Mulaney comes out swinging in his return to the stage.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisAnimal Crackers (1930)
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 goes missing. The intrepid Captain Spaulding attempts to solve the crime with the help of his silly secretary Horatio Jamison, while sparring with the anarchic Signor Emanuel Ravelli and his nutty sidekick The Professor.
Why it matches: Recommended by TMDB viewers · both comedy & music
Popcorn FlickMovies like thisGodspell (1973)
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.
Why it matches: Recommended by TMDB viewers · both comedy & music
Popcorn FlickMovies like thisShane Gillis: Beautiful Dogs (2023)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisGabriel Iglesias: Hot and Fluffy (2007)
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 you can see Comedy Central's "Comic of the Year" in his sold-out performance at the historic Fox Theatre in Bakersfield, California!
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisTaylor Tomlinson: Have It All (2024)
Can Taylor Tomlinson have it all? From dating woes to dream jobs to inventive dirty talk, she shares life's ups and downs in this stand-up comedy special.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJim Gaffigan: Quality Time (2019)
Comedian Jim Gaffigan performs live at the State Theatre in Minneapolis, MN.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisCB4 (1993)
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 rap music as they claim... but a lack of musical ability in an artist never hurts sales, does it? You've just got to play the part of a rap star...
Why it matches: Recommended by TMDB viewers · both comedy & music
Popcorn FlickMovies like thisDave Chappelle: Killin' Them Softly (2000)
Dave Chappelle returns for a stand-up to D.C. and riffs on politics, police, race relations, drugs, Sesame Street and more.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies like thisJohn Mulaney: Kid Gorgeous at Radio City (2018)
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies like thisAdam Sandler: 100% Fresh (2018)
Adam Sandler takes his comical musical musings back out on the road, from comedy clubs to concert halls to one very unsuspecting subway station.
Why it matches: Recommended by TMDB viewers · both comedy & music
Worth the HypeMovies like thisDave Chappelle: The Closer (2021)
As he closes out his slate of comedy specials, Dave takes the stage to try and set the record straight — and get a few things off his chest.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisSmosh LIVE (2016)
The very first Smosh live stream with sketches and challenges performed live by Ian, Anthony, Olivia, Noah, Courtney, Keith, and Shayne.
Why it matches: Similar story and style · both comedy
Television Parts Home Companion (1985)
A 40-minute compilation of comedy skits and music taken from the series "Michael Nesmith in Television Parts."
Why it matches: Similar story and style · both comedy & music
Saturday Night Live: The Best of Dana Carvey (1999)
From 1986 to 1993 Dana Carvey dominated the stage at Saturday Night Live with dead-on impressions and some of the most popular characters in SNL history. See the best of the Church Lady, Hans and Franz, George Bush, Ross Perot, Sassive Headwound Harry, Wayne's World and many others. Plus there's extra material, including Dana's favorite scenes that were cut after Dress Rehearsal and never seen before now.
Why it matches: Similar story and style · both comedy
Harlem on the Prairie (1937)
A wandering cowboy helps the daughter of a former outlaw find the gold her father stole twenty years earlier and return it to its owners.
Why it matches: Similar story and style · both music & comedy
Saturday Night Live: Christmas (1999)
Join the epic "Not Ready for Prime Time Players" cast of Saturday Night Live regulars in a hilarious compilation of the best holiday moments from the show's Christmas specials. Some of the highlights include "Martha Stewart's Topless Christmas Special," "The Lost Ending to It's a Wonderful Life," "The Night Hannukah Harry Saved Christmas," "Mr. Robinson's Neighborhood on Christmas" and, of course, the Church Lady's drum solo.
Why it matches: Similar story and style · both comedy
All Commercials... A Steve Martin Special (1980)
Steve Martin's third NBC special serves as a salute to 1970s television commercials. Taking shots at everything from "Suzy Chapstick" to Palmolive to advertising agencies, this special showcased Martin's genius for physical comedy.
Why it matches: Similar story and style · both comedy
Honey (2003)
Honey Daniels dreams of making a name for herself as a hip-hop choreographer. When she's not busy hitting downtown clubs with her friends, she teaches dance classes at a nearby community center in Harlem, N.Y., as a way to keep kids off the streets. Honey thinks she's hit the jackpot when she meets a hotshot director casts her in one of his music videos. But, when he starts demanding sexual favors from her, Honey makes a decision that will change her life.
Why it matches: Similar story and style · both music
Popcorn FlickMovies like thisMonty Python Live at the Hollywood Bowl (1982)
Monty Python perform many of their greatest sketches at the Hollywood Bowl, including several from pre-Python days.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisUncle Drew (2018)
Uncle Drew recruits a squad of older basketball players to return to the court to compete in a tournament.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisSparkle (1976)
Three sisters start out singing in their church choir in Harlem in the late 1950s and become a successful girl group in the 1960s.
Why it matches: Similar story and style · both music
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Frequently asked questions
What are the best movies like The Strolling '20s?
The closest matches to The Strolling '20s are The Rutles: All You Need Is Cash (1978), Steve Martin and Martin Short: An Evening You Will Forget for the Rest of Your Life (2018) and Dolly Parton's Christmas on the Square (2020). Below are 27 more, each with the reason it matches.
What should I watch after The Strolling '20s?
Start with The Rutles: All You Need Is Cash (1978), the closest match to The Strolling '20s.
What is the highest-rated movie like The Strolling '20s?
Bo Burnham: Make Happy (2016), rated 8.0/10 by 459 TMDB users.
What is the newest movie like The Strolling '20s?
Bill Burr: Drop Dead Years (2025) is the most recent release on this list.
Are there English movies like The Strolling '20s?
Yes: The Rutles: All You Need Is Cash (1978), Steve Martin and Martin Short: An Evening You Will Forget for the Rest of Your Life (2018) and Dolly Parton's Christmas on the Square (2020).
How are movies similar to The Strolling '20s chosen?
First come films that Trakt’s viewers watch alongside The Strolling '20s, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.