Movies Like Michael Sheen Presents - You're The Boss

If you liked Michael Sheen Presents - You're The Boss (2009), a comedy movie, 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
Mike Bassett: England Manager (2001)
★ 7/10Also comedy
After England's football (soccer) manager has a heart attack, Mike Bassett is hired as the new manager and promptly announces the team will win the World Cup.
2
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.
3
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.
4
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…
5
The Air Up There (1994)
★ 6.1/10Also comedy
Jimmy Dolan is a college basketball coach who wants a big promotion. To get it, he needs to make a dramatic find. He ends up deep in Africa, hoping to recruit Saleh, a huge basketball prodigy Jimmy glimpsed in a home…
6
Rookie of the Year (1993)
★ 6.2/10Also comedy
When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.
7
Eddie Murphy Raw (1987)
★ 7.2/10Also comedy
Eddie Murphy delights, shocks and entertains with dead-on celebrity impersonations, observations on '80s love, sex and marriage, a remembrance of Mom's hamburgers and much more.
8
The Paper Tigers (2020)
★ 6.7/10Also comedy
Three middle aged men polish their martial arts skills to avenge their fallen master.
9
Jerry Seinfeld: 23 Hours to Kill (2020)
★ 6.2/10Also comedy
Jerry Seinfeld takes the stage in New York and tackles talking vs. texting, bad buffets vs. so-called "great" restaurants and the magic of Pop Tarts.
10
Ricky Gervais: Humanity (2018)
★ 7.6/10Also comedy
In his first special in seven years, Ricky Gervais slings his trademark snark at celebrity, mortality and a society that takes everything personally.
11
Grimsby (2016)
★ 6/10Also comedy
Wrongfully accused and on the run, a top MI6 assassin joins forces with his long-lost, football hooligan brother to save the world from a sinister plot.
12
A Bad Moms Christmas (2017)
★ 6.3/10Also comedy
Amy, Kiki and Carla – three under-appreciated and over-burdened women – rebel against the challenges and expectations of the Super Bowl for mothers: Christmas. And if creating a more perfect holiday for their families…
13
Louis C.K.: Ridiculous (2026)
★ 6.1/10Also comedy
From a bee getting shot in New York City to paying strangers to take his aging father, Louis C.K. unleashes the ridiculous thoughts in his mind.
14
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
15
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.
16
Louis C.K.: Hilarious (2010)
★ 7.8/10Also comedy
In this unique and dynamic live concert experience, Louis C.K.'s exploration of life after 40 destroys politically correct images of modern life with thoughts we have all had...but would rarely admit to.
17
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.
18
The Roast of Tom Brady (2024)
★ 6.7/10Also comedy
Offensive lines. Full-contact comedy. Kevin Hart hosts this all-star roast of NFL legend Tom Brady.
19
Ricky Gervais: Mortality (2025)
★ 7/10Also comedy
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
20
Chris Rock: Never Scared (2004)
★ 7.5/10Also comedy
Chris Rock, the three-time Emmy Award-winner, comedian, actor, and host of HBO's acclaimed The Chris Show, stars in his fourth solo stand-up special for HBO, Chris Rock: Never Scared. Featuring his unique, insightful…