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Movies that feel like The Boss of It All (2006)

If you loved The Boss of It All, the closest films we have are The Idiots (1998), Adrift in Tokyo (2007) and The Invisible Woman (2009). All three share The Boss of It All's witty and playful feel, which is what we rank on before quality. 3 of the 12 picks below are included with a subscription right now on Amazon Prime Video and MUBI and others, checked against today's data.

The owner of an Information Technology firm wants to sell his business for profit. The trouble is that when he started his firm he invented a nonexistent company president to hide behind when unpopular steps needed to be taken. When potential purchasers insist on negotiating with the "Boss" face to face the owner has to hire a failed actor to play the part.

🍅 74% Rotten Tomatoes6.6 IMDb ↗TMDB ↗dir. Lars von Trierwittyplayful
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If The Boss of It All hit the spot, these will too

The Idiots poster
The Idiots
1998 · dir. Lars von Trier
🍅 73%6.7comedy · drama

Both are Lars von Trier's work, and they rhyme

The difference: Leans harder into drama than The Boss of It All does

A group of people gather at a Copenhagen suburban home to break all the limitations and to bring out the 'inner idiot' in themselves.

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Adrift in Tokyo poster
Adrift in Tokyo
2007 · dir. Satoshi Miki
7.2comedy

Both land wit and play at once

A thug offers to pay a law student's gambling debt if the student will accompany him on a trip across Tokyo.

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The Invisible Woman poster
The Invisible Woman
2009 · dir. Cláudio Torres
6.3comedy

Comedy built on wit, twice over

A man is abandoned by his wife and then falls in love with his neighbor, the perfect, ideal woman. The only problem: she doesn't exist!

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The Green Butchers poster
The Green Butchers
2003 · dir. Anders Thomas Jensen
🍅 63%7.2comedy

Playful comedy, and it commits to that

Svend and Bjarne work for a butcher in a small Danish town. Fed up with their boss' arrogance, they decide to start their own butcher shop. After dismal beginnings, an unfortunate accident happens which coincides with a large order of meat. One hasty decision leads to another and soon the business thrives. In the meantime, Bjarne has to deal with his twin brother who has been in coma for years following a gruesome car accident.

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Head Over Heels poster
Head Over Heels
2010 · dir. Roberto Santucci
5.7comedy

Witty comedy in both cases

After being left by her husband and fired from her work, a workaholic, thirtysomething businesswoman is forced to go through a big change in her life and becomes a partner on a decadent sex shop.

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Meu Passado Me Condena: O Filme poster
Meu Passado Me Condena: O Filme
2013 · dir. Julia Rezende
5.8comedy

Both run playful where it counts

The immature and cheap douche bag Fábio Clóvis marries the pseudo-intellectual Miá and they travel in a cruise to Europe on board of a fancy passenger vessel. Fabio and Miá are invited to have dinner with the wealthy Beto Assunção and his gorgeous wife Laura in a VIP restaurant on the vessel. Soon Fábio discovers that Beto was Miá's boyfriend and Miá learns that Fábio had a crush on Laura that was his classmate. Meanwhile the cynical chamber maid Suzana Mello and her estranged husband, the entertainer Wilson, make a bet that Fábio and Miá will split before the end of the trip and poison their relationship. When the ship arrives in Casablanca, Fábio meets his bothersome childhood friend Cabeça that affects their honeymoon.

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Till Luck Do Us Part poster
Till Luck Do Us Part
2012 · dir. Roberto Santucci
5.5comedy

Comedy approached the same way

Check out the hilarious story of luck and misadventures of Tino, a family man whose life is transformed after he wins the lottery. Dazzled by wealth, this boaster spends all his money on a life of luxury and ostentation. But after finding out that he is bankrupt, he faces comical situations: besides not telling his wife he is broke because she is pregnant and cannot get upset, Tino must accept help from his neighbor who is an extremely thrifty financial adviser and the only one capable of getting him out of the rut.

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Best Worst Movie poster
Best Worst Movie
2009 · dir. Michael Stephenson
🍅 94%7.2documentary · comedy

Comedy of the same temperament

A look at the making of the film Troll 2 (1990) and its journey from being crowned the "worst film of all time" to a cherished cult classic.

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Winnebago Man poster
Winnebago Man
2010 · dir. Ben Steinbauer
🍅 90%7.2documentary · comedy

Both are comedy through and through

Jack Rebney is the most famous man you've never heard of - after cursing his way through a Winnebago sales video, Rebney's outrageously funny outtakes became an underground sensation and made him an internet superstar. Filmmaker Ben Steinbauer journeys to the top of a mountain to find the recluse who unwittingly became the "Winnebago Man".

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Till Luck Do Us Part 2 poster
Till Luck Do Us Part 2
2013 · dir. Roberto Santucci
4.9comedy

Comedy in the same key

After all the trouble in the first film, Tino and Jane have more fun adventures. Still tasting bitter failure, they see a light at the end of the tunnel with uncle Olavinho’s unexpected inheritance. However, the will carries an unusual request: the rich uncle wants his ashes to be scattered throughout the Grand Canyon. The couple takes the opportunity of the trip to fulfill this wish and decides to go to Las Vegas and end up getting into comical situations. Big time spender Tino will fall into the greatest temptations and indulge in the casinos of the gambling city.

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My Mom Is a Character 2 poster
My Mom Is a Character 2
2016 · dir. César Rodrigues
6.6comedy

The comedy is handled with the same confidence

Dona Hermínia is back, but now rich and famous since she is the host of her own successful TV show. However, the overprotective character will have to deal with her children's departures, as Marcelina and Juliano decide to move out. In counterpart, she will welcome, as a visitor, her sister Lúcia Helena, who's been living in New York.

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Clockwise poster
Clockwise
1986 · dir. Christopher Morahan
🍅 83%6.6comedy

Both working the same comedy territory

The difference: 20 years apart, and the 1980s show

School headmaster Brian Stimpson is obsessed with timeliness, order, and discipline. Brian misses his train after meticulously preparing a speech for an education conference. With no one else to turn to, he asks young former student Laura Wisely for a ride. Laura, upset over a break-up, agrees to drive him in her parents' car - which alarms her mother and father, who worry that she has run away with a married man and subsequently alert the police.

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The best-reviewed films that share The Boss of It All’s defining feeling.