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Movies Like 20 Questions

Find movies like 20 Questions using TMDB similarity plus Movie Rankings community context. Our top current pick is Too Funny to Fail: The Life & Death of The Dana Carvey Show. Browse 18 related titles with direct links to rankings, cast pages, and matchup data.

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Too Funny to Fail: The Life & Death of The Dana Carvey Show

2017

It had all the makings of a huge television success: a white-hot comic at the helm, a coveted primetime slot, and a pantheon of future comedy legends in the cast and crew. So why did The Dana Carvey Show—with a writers room and cast including then unknowns Steve Carell, Stephen Colbert, Louis C.K., Robert Smigel, Charlie Kaufman, and more— crash and burn so spectacularly? TOO FUNNY TO FAIL tells the hilarious true story of a crew of genius misfits who set out to make comedy history… and succeeded in a way they never intended.

TMDB Recommended

Quiz Show

1994

Herbert Stempel's transformation into an unexpected television personality unfolds as he secures victory on the cherished American game show, 'Twenty-One.' However, when the show introduces the highly skilled contestant Charles Van Doren to replace Stempel, it compels Stempel to let out his frustrations and call out the show as rigged. Lawyer Richard Goodwin steps in and attempts to uncover the orchestrated deception behind the scenes.

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Hellzapoppin'

1941

Olsen and Johnson, a pair of stage comedians, try to turn their play into a movie and bring together a young couple in love, while breaking the fourth wall every step of the way.

TMDB Recommended

Bill 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.

TMDB Recommended

Lucy and Desi

2022

Explore the unlikely partnership and enduring legacy of one of the most prolific power couples in entertainment history. Lucille Ball and Desi Arnaz risked everything to be together.

TMDB Recommended

Talk Radio

1988

A rude, contemptuous talk show host becomes overwhelmed by the hatred that surrounds his program just before it goes national.

TMDB Recommended

Nerve

2016

Industrious high school senior Vee Delmonico has had it with living life on the sidelines. When pressured by friends to join the popular online game Nerve, Vee decides to sign up for just one dare in what seems like harmless fun. But as she finds herself caught up in the thrill of the adrenaline-fueled competition partnered with a mysterious stranger, the game begins to take a sinister turn with increasingly dangerous acts, leading her into a high stakes finale that will determine her entire future.

TMDB Recommended

Nas: Time Is Illmatic

2014

Time Is Illmatic is a feature length documentary film that delves deep into the making of Nas' 1994 debut album, Illmatic, and the social conditions that influenced its creation.

TMDB Recommended

Quiz Lady

2023

A brilliant but tightly wound, gameshow-obsessed young woman, Anne, and her estranged, train-wreck of a sister, Jenny, must work together to help cover their mother's gambling debts. When Anne's beloved dog is kidnapped, they set out on a wild, cross-country trek to get the cash the only way they know how: by turning Anne into a bona-fide gameshow champion.

TMDB Recommended

UHF

1989

The eccentric new manager of a UHF television channel tries to save the station from financial ruin with an odd array of programming.

TMDB Recommended

Everything You Always Wanted to Know About Sex *But Were Afraid to Ask

1972

A collection of seven vignettes, which each address a question concerning human sexuality. From aphrodisiacs to sexual perversion to the mystery of the male orgasm, characters like a court jester, a doctor, a queen and a journalist adventure through lab experiments and game shows, all seeking answers to common questions that many would never ask.

TMDB Recommended

Bad Words

2013

Forty-year-old misanthrope, Guy Trilby, enters the National Golden Quill Spelling Bee through a loophole in the rules.

TMDB Recommended

The Luckiest Man in America

2025

1984; Michael Larson, an unemployed ice-cream truck driver from Ohio, steps onto the game show "Press Your Luck" harboring a secret: the key to endless amounts of money. But his winning streak is threatened when the executives in the control room start to uncover his real motivations.

TMDB Recommended

Oscar

1991

Angelo "Snaps" Provolone made his dying father a promise on his deathbed: he would leave the world of crime and become an honest businessman. Despite having no experience in making money in a legal fashion, Snaps sets about to keep his promise.

TMDB Recommended

Watching the Detectives

2007

Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life femme fatale, his mundane world gets turned upside down and the line between reality and the movies quickly begins to blur.

TMDB Recommended

It's a Disaster

2013

Four couples meet for Sunday brunch only to discover they are stuck in a house together as the world may be about to end.

TMDB Recommended

The Aristocrats

2005

One hundred superstar comedians tell the same very, VERY dirty, filthy joke--one shared privately by comics since Vaudeville.

TMDB Recommended

Between Two Ferns: The Movie

2019

Galifianakis dreamed of becoming a star. But when Will Ferrell discovered his public access TV show, 'Between Two Ferns' and uploaded it to Funny or Die, Zach became a viral laughing stock. Now Zach and his crew are taking a road trip to complete a series of high-profile celebrity interviews and restore his reputation.

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Too Funny to Fail: The Life & Death of The Dana Carvey Show is the strongest current recommendation on this page for viewers looking for movies like 20 Questions.

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This page currently lists 18 related titles for 20 Questions.

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