Movies Like The Boss

If you liked The Boss (2016), a comedy movie directed by Ben Falcone, 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
Married to the Mob (1988)
★ 6/10Also comedy
Angela de Marco is fed up with her gangster husband's line of work and wants no part of the crime world. When her husband is killed for having an affair with the mistress of mob boss Tony "The Tiger" Russo, Angela and…
2
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10Also comedy
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
3
Horrible Bosses (2011)
★ 6.6/10Also comedy
For Nick, Kurt and Dale, the only thing that would make the daily grind more tolerable would be to grind their intolerable bosses into dust. Quitting is not an option, so, with the benefit of a few-too-many drinks and…
4
Eenie Meanie (2025)
★ 6.3/10Also comedy
A former teenage getaway driver gets dragged back into her unsavory past when a former employer offers her a chance to save the life of her chronically unreliable ex-boyfriend.
5
The Stöned Age (1994)
★ 6.1/10Also comedy
Determined to avoid another night of driving aimlessly around Torrance in the Blue Torpedo, Joe and Hubbs set out on a quest for fine chicks. Their paths soon cross with Tack, from whom they learn about a pair of…
6
Idiots (2026)
★ 6.3/10Also comedy
Two rock-bottom drivers transport a wealthy teen to rehab, but their simple job spirals into a chaotic journey of drugs, danger, and crime as their passenger derails their plans.
7
Gail Daughtry and the Celebrity Sex Pass (2026)
★ 6.4/10Also comedy
After her fiance sleeps with his celebrity crush, Kansas hairdresser Gail heads to Hollywood to even the score with her own famous fantasy — Jon Hamm.
8
Barb & Star Go to Vista Del Mar (2021)
★ 6/10Also comedy
The story of best friends Barb and Star, who leave their small midwestern town for the first time to go on vacation in Vista Del Mar, Florida, where they soon find themselves tangled up in adventure, love, and a…
9
A Million Ways to Die in the West (2014)
★ 6/10Also comedy
As a cowardly farmer begins to fall for the mysterious new woman in town, he must put his new-found courage to the test when her husband, a notorious gun-slinger, announces his arrival.
10
Analyze That (2002)
★ 5.8/10Also comedy
The mafia's Paul Vitti is back in prison and will need some serious counseling when he gets out. Naturally, he returns to his analyst Dr. Ben Sobel for help and finds that Sobel needs some serious help himself as he…
11
Extract (2009)
★ 5.9/10Also comedy
The owner of a factory that produces flavor extracts, Joel Reynold seems to have it all, but really doesn't. What's missing is sexual attention from his wife, Suzie. Joel hatches a convoluted plan to get Suzie to cheat…
12
Office Space (1999)
★ 7.4/10Also comedy
A depressed white-collar worker tries hypnotherapy, only to find himself in a perpetual state of devil-may-care bliss that prompts him to start living by his own rules, and hatch a hapless attempt to embezzle money…
13
This Is 40 (2012)
★ 5.9/10Also comedy
Pete and Debbie are both about to turn 40, their kids hate each other, both of their businesses are failing, they're on the verge of losing their house, and their relationship is threatening to fall apart.
14
Adult World (2014)
★ 6/10Also comedy
Amy, a naive college graduate who believes she's destined to be a great poet, begrudgingly accepts a job at a sex shop while she pursues a mentorship with reclusive writer Rat Billings.
15
Clerks II (2006)
★ 6.9/10Also comedy
A calamity at Dante and Randall's shops sends them looking for new horizons - but they ultimately settle at Mooby's, a fictional Disney-McDonald's-style fast-food empire.
16
Stir Crazy (1980)
★ 6.5/10Also comedy
New Yorkers Skip Donahue and Harry Monroe have no jobs and no prospects, so they decide to flee the city and find work elsewhere, landing jobs wearing woodpecker costumes to promote the opening of a bank. When their…
17
American Reunion (2012)
★ 6.4/10Also comedy
The characters we met a little more than a decade ago return to East Great Falls for their high school reunion. In one long-overdue weekend, they will discover what has changed, who hasn’t, and that time and distance…
18
Soul Men (2008)
★ 6.2/10Also comedy
Two former backup soul singers, Louis and Floyd, have not spoken to each other in 20 years, and reluctantly agree to travel across the country together to a reunion concert to honor their recently-deceased lead singer…
19
Senior Year (2022)
★ 5.9/10Also comedy
A 37-year-old woman wakes up from a 22-year coma, and returns to the high school where she was once a popular cheerleader to finish her senior year and become prom queen.
20
3000 Miles to Graceland (2001)
★ 5.9/10Also comedy
It was an ingenious enough plan: rob the Riviera Casino's count room during an Elvis impersonator convention. But Thomas Murphy decided to keep all the money for himself and shot all his partners, including…