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Movies that feel like Head Over Heels (2010)

If you loved Head Over Heels, the closest films we have are Till Luck Do Us Part (2012), Till Luck Do Us Part 2 (2013) and Meu Passado Me Condena: O Filme (2013). All three share Head Over Heels' 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.

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.

5.7 IMDb ↗TMDB ↗dir. Roberto Santucciwittyplayful

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If Head Over Heels hit the spot, these will too

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

Roberto Santucci working the same nerve twice

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

Roberto Santucci directing both, with the same fingerprints on each

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

Both land wit and play at once

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

Witty comedy, and it commits to that

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

Playful comedy in both cases

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 Boss of It All poster
The Boss of It All
2006 · dir. Lars von Trier
🍅 74%6.6comedy

Comedy with a pulse of wit, in both cases

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.

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

The shared currency is play

The difference: Sits closer to documentary than Head Over Heels does

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

Comedy approached the same way

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

Both know what they want from comedy

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

The same comedy instincts

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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My Mom Is a Character poster
My Mom Is a Character
2013 · dir. André Pellenz
6.8comedy

The comedy is handled with the same confidence

After another spat with her kids, Dona Hermínia decides to take some time off from them and hides away in her aunt's house, where she reminisces about her kids in an age when they still needed her.

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The Santa Claus Gang poster
The Santa Claus Gang
2010 · dir. Paolo Genovese
5.9comedy

Both are comedy through and through

On Christmas Eve, three friends dressed as Santa Claus are arrested in what looks like an attempted burglary and charged with being the infamous "Santa Claus Gang". While trying to prove their innocence to the police, the trio explains why they found themselves in such a strange situation...

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The best-reviewed films that share Head Over Heels’ defining feeling.