Movies Like The Secret of My Success

If you liked The Secret of My Success (1987), a comedy movie directed by Herbert Ross, 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
Thunderstruck (2012)
★ 6.2/10Also comedy
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.
2
Taking Care of Business (1990)
★ 6.3/10Also comedy
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
3
The Importance of Being Earnest (1952)
★ 7.2/10Also comedy
Two young gentlemen living in 1890s England use the same pseudonym ('Ernest') on the sly, which is fine until they both fall in love with women using that name, which leads to a comedy of mistaken identities.
4
The Distinguished Gentleman (1992)
★ 6/10Also comedy
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…
5
Oscar (1991)
★ 6.4/10Also comedy
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…
6
Tower Heist (2011)
★ 6.1/10Also comedy
A luxury condo manager leads a staff of workers to seek payback on the Wall Street swindler who defrauded them. With only days until the billionaire gets away with the perfect crime, the unlikely crew of amateur…
7
Bullets Over Broadway (1994)
★ 7.1/10Also comedy
After young playwright, David Shayne obtains funding for his play from gangster Nick Valenti, Nick's girlfriend Olive miraculously lands the role of a psychiatrist—but not only is she a bimbo who could never pass for a…
8
Problemista (2024)
★ 6.7/10Also comedy
Alejandro is an aspiring toy designer from El Salvador, struggling to bring his unusual ideas to life in New York City. As time on his work visa runs out, a job assisting an erratic art-world outcast becomes his only…
9
Much Ado About Nothing (2013)
★ 6.8/10Also comedy
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
10
Little Big League (1994)
★ 6/10Also comedy
When the owner of the Minnesota Twins passes away, he bequeaths the team to his preteen grandson. The newly minted head honcho quickly appoints himself manager, causing unrest in an organization that struggles to take…
11
The Errand Boy (1961)
★ 6.2/10Also comedy
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…
12
Analyze This (1999)
★ 6.5/10Also comedy
Countless wiseguy films are spoofed in this film that centers on the neuroses and angst of a powerful Mafia racketeer who suffers from panic attacks. When Paul Vitti needs help dealing with his role in the "family,"…
13
About My Father (2023)
★ 6/10Also comedy
Encouraged by his girlfriend Ellie, Sebastian and his Italian immigrant father, Salvo, spend the 4th of July weekend with her wealthy and exceedingly eccentric family. The gathering soon develops into a culture clash…
14
Playdate (2025)
★ 6.2/10Also comedy
When out-of-work accountant Brian joins stay-at-home dad Jeff for a playdate with their sons, he expects a laid-back afternoon. Instead, they're chased by mercenaries, and Brian—totally unprepared—must survive one…
15
The Mouse That Roared (1959)
★ 6.4/10Also comedy
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…
16
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
★ 7/10Also comedy
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
17
Mistress America (2015)
★ 6.5/10Also comedy
A college freshman cures her disappointment and loneliness by allowing herself to be pulled into the wacky schemes of her future stepsister.
18
Duplex (2003)
★ 6.1/10Also comedy
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
19
Romy and Michele's High School Reunion (1997)
★ 6.2/10Also comedy
Two not-too-bright party girls reinvent themselves for their high school reunion. Armed with a borrowed Jaguar, new clothes and the story of their success as the inventors of Post-It notes, Romy and Michele descend on…
20
The Slammin' Salmon (2009)
★ 5.8/10Also comedy
The brutal former heavyweight boxing champion Cleon "Slammin'" Salmon (Duncan), now owner of a Miami restaurant, institutes a competition to see which waiter can earn the most money in one night: the winner stands to…