Movies like The First $20 Million Is Always the Hardest (2002)
The best movies like The First $20 Million Is Always the Hardest (2002) are Thunderstruck (2012), The Million Pound Note (1954) and The Errand Boy (1961). If The First $20 Million Is Always the Hardest hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedWithnail & I (1987)7.2/10 from 657 votes
- NewestLeucosélidophilie (2026)Released 2026
Thunderstruck (2012)
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Million Pound Note (1954)
An impoverished American sailor is fortunate enough to be passing the house of two rich gentlemen who have conceived the crazy idea of distributing a note worth one million pounds. The sailor finds that whenever he tries to use the note to buy something, people treat him like a king and let him have whatever he likes for free. Ultimately, the money proves to be more troublesome than it is worth when it almost costs him his dignity and the woman he loves.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe Errand Boy (1961)
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 ever finds is that he can cause havoc no matter what he does.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMistress America (2015)
A college freshman cures her disappointment and loneliness by allowing herself to be pulled into the wacky schemes of her future stepsister.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSleeper (1973)
Miles Monroe, a clarinet-playing health food store proprietor, is revived out of cryostasis 200 years into a future world in order to help rebels fight an oppressive government regime.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisGrown Ups 2 (2013)
Lenny has relocated his family back to the small town where he and his friends grew up. This time around, the grown ups are the ones learning lessons from their kids on a day notoriously full of surprises—the last day of school.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisStewie Griffin: The Untold Story (2005)
The maniacal baby of the Griffin family, Stewie, meets his future self. In doing this he discovers that his future image is not what he has anticipated because of a near death experience.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Mouse That Roared (1959)
The Duchy of Grand Fenwick decides that the only way to get out of their economic woes is to declare war on the United States, lose and accept foreign aid. They send an invasion force (in chain mail, armed with bows and arrows) to New York and they arrive during a nuclear drill that has cleared the streets.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Distinguished Gentleman (1992)
A Florida con man uses the recent death of the long time Congressman from his district, who he just happens to share a last name with, to get elected to his version of paradise, the U.S. Congress, where the money flows from lobbyists.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisChris Rock: Kill the Messenger (2008)
An HBO special edited from three performances from Chris Rock's 2008 comedy tour: London (dark suit, dark shirt), Johannesburg (black suit, white shirt) and New York (shiny jacket). Topics include the ongoing presidential campaign, the possibility of a black president, George W. Bush, gas prices, low-paid jobs, ringtones and bottled water, sex, relationships and the correct use of the n-word
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe Ladies Man (1961)
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 all these females?
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisKevin Hart: Laugh at My Pain (2011)
Experience the show that quickly became a national phenomenon. Get an up-close and personal look at Kevin back in Philly where he began his journey to become one of the funniest comedians of all time.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisBack to the Beach (1987)
A former beach boy and his wife go to California to visit their daughter and become part of the new beach scene.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisGabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies 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 thisWayne's World (1992)
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 of a sleazy network executive who wants to produce a big-budget version of "Wayne's World"—and he also wants Wayne's girlfriend, a rock singer named Cassandra. Wayne and Garth have to battle the executive not only to save their show, but also Cassandra.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJohnny English Strikes Again (2018)
Disaster strikes when a criminal mastermind reveals the identities of all active undercover agents in Britain. The secret service can now rely on only one man - Johnny English. Currently teaching at a minor prep school, Johnny springs back into action to find the mysterious hacker. For this mission to succeed, he’ll need all of his skills - what few he has - as the man with yesterday’s analogue methods faces off against tomorrow’s digital technology.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Silencers (1966)
Matt Helm is called out of retirement to stop the evil Big O organization who plan to explode an atomic bomb over Alamagordo, NM, and start WW III.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisClass Rank (2017)
Two high school misfits join forces in an attempt to overtake the local school board. Guided by their families, they enter the perilous word of politics and, in the process, learn a thing or two about love.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDark Star (1974)
A group of scientists are sent on a mission to destroy unstable planets. Twenty years into their mission, they have to battle their alien mascot as well as a "sensitive" and intelligent bombing device that starts to question the meaning of its existence.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDon's Party (1976)
On the night of the 1969 federal election, Don Henderson invites a group of friends to celebrate a predicted Labor Party victory, much to the dismay of his wife, Kath. The Hendersons and their nine guests drink, joke, make love, and fight, all while coming to terms with their individual struggles in life.
Why it matches: Similar story and style · both comedy
The Crimson Permanent Assurance (1983)
A group of down-and-out accountants mutiny against their bosses and sail their office building onto the high seas in search of a pirate's life.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisDownsizing (2017)
A kindly occupational therapist undergoes a new procedure to be shrunken to four inches tall so that he and his wife can help save the planet and afford a nice lifestyle at the same time.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisDear God (1996)
A judge gives con-man Tom Turner a choice—a jail sentence, or a year of honest work. But when he gets a job in the U.S. Post Office's dead letter office, he starts a Good Samaritan con by answering letters written to God. His seemingly virtuous work inspires his co-workers to do the same, but their good deeds are frowned upon by the postmaster general—and the cops.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisHangover (2014)
The film showcases four friends from different tiers of society and how despite their devil-may-care personas rise up to tackle an incident in their lives
Why it matches: Similar story and style · both comedy
Money Ratnam (2014)
Neil, a showroom executive, finds a bag full of money after a party. He receives a call to meet at a secluded spot where he finds four strangers and gets involved in a dangerous deal.
Why it matches: Similar story and style · both comedy
Modern Cinderella (1965)
Katerina, a poor girl, finds a job as a secretary and falls in love with her boss on a trip to Rome.
Why it matches: Similar story and style · both comedy
Middle Men (2009)
Chronicles Jack Harris, one of the pioneers of internet commerce, as he wrestles with his morals and struggles not to drown in a sea of conmen, mobsters, drug addicts, and pornstars.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisWithnail & I (1987)
Two out-of-work actors -- the anxious, luckless Marwood and his acerbic, alcoholic friend, Withnail -- spend their days drifting between their squalid flat, the unemployment office and the pub. When they take a holiday "by mistake" at the country house of Withnail's flamboyantly gay uncle, Monty, they encounter the unpleasant side of the English countryside: tedium, terrifying locals and torrential rain.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like The First $20 Million Is Always the Hardest?
The closest matches to The First $20 Million Is Always the Hardest are Thunderstruck (2012), The Million Pound Note (1954) and The Errand Boy (1961). Below are 27 more, each with the reason it matches.
What should I watch after The First $20 Million Is Always the Hardest?
Start with Thunderstruck (2012), the closest match to The First $20 Million Is Always the Hardest.
What is the highest-rated movie like The First $20 Million Is Always the Hardest?
Withnail & I (1987), rated 7.2/10 by 657 TMDB users.
What is the newest movie like The First $20 Million Is Always the Hardest?
Leucosélidophilie (2026) is the most recent release on this list.
Are there English movies like The First $20 Million Is Always the Hardest?
Yes: Thunderstruck (2012), The Million Pound Note (1954) and The Errand Boy (1961).
How are movies similar to The First $20 Million Is Always the Hardest chosen?
First come films that Trakt’s viewers watch alongside The First $20 Million Is Always the Hardest, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.