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Movies like Smoking Cuban Style (1999)

The best movies like Smoking Cuban Style (1999) are Fun with Dick and Jane (1977), Chief Daddy 2: Going for Broke (2021) and Men in the City 2 (2011). If Smoking Cuban Style hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Fun with Dick and Jane (1977)

    When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.

    Why it matches: Recommended by TMDB viewers · both comedy

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  2. Chief Daddy 2: Going for Broke (2021)

    The Beecroft family are ready to spend all of Chief Daddy's inheritance, but not if the CEO of his company has anything to do with it.

    Why it matches: Recommended by TMDB viewers · both comedy

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  3. Men in the City 2 (2011)

    The sequel of the "Men in the city" movie which reunites all the characters.

    Why it matches: Recommended by TMDB viewers · both comedy

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  4. Who's Minding the Store? (1963)

    Norman Phiffer, a proud man in a humble life, doesn't know that his girlfriend, Barbara, is heir to the Tuttle Department Store dynasty. Mrs. Tuttle, Barbara's mother, is determined to split the two lovers, and hires Norman in an attempt to humiliate him enough that Barbara leaves him. Will she ruin their love, or will he ruin her store?

    Why it matches: Recommended by TMDB viewers · both comedy

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  5. Class Rank (2017)

    Two high school misfits join forces in an attempt to overtake the local school board. Guided by their families, they enter the perilous word of politics and, in the process, learn a thing or two about love.

    Why it matches: Recommended by TMDB viewers · both comedy

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  6. After the Ball (2015)

    After the Ball, a retail fairy tale set in the world of fashion. Kate's dream is to design for couturier houses. Although she is a bright new talent, Kate can't get a job. No one trusts the daughter of Lee Kassell, a retail guru who markets clothes "inspired" by the very designers Kate wants to work for. Who wants a spy among the sequins and stilettos? Reluctantly, Kate joins the family business where she must navigate around her duplicitous stepmother and two wicked stepsisters. But with the help of a prince of a guy in the shoe department her godmother's vintage clothes and a shocking switch of identities, Kate exposes the evil trio, saves her father's company -- and proves that everyone can wear a fabulous dress.

    Why it matches: Recommended by TMDB viewers · both comedy

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  7. Much Ado About Nothing (2013)

    A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.

    Why it matches: Recommended by TMDB viewers · both comedy

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  8. Shane Gillis: Beautiful Dogs (2023)

    In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  9. The Awakening of Motti Wolkenbruch (2018)

    The young Orthodox Jew, Motti Wolkenbruch, finds himself at a turning point. His beloved mother wants him to get married and presents one marriage candidate after the other. Unfortunately none of the woman pleases him, because they all look just like her. The situation gets even more complicated, when Motti secretly falls in love with the non-Jewish girl Laura, a so-called Shiksa.

    Why it matches: Recommended by TMDB viewers · both comedy

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  10. The Manny (2015)

    Young industrialist Clemens Klina doesn't have time for his children and accidentally hires a man who actually came to him, seeking revenge, as a nanny for them.

    Why it matches: Recommended by TMDB viewers · both comedy

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  11. Thunderstruck (2012)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

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  12. Kokowääh 2 (2013)

    Who said a patchwork family is without problems? Two years after the turbulence of Kokowääh, everyday life turns to everyday chaos…

    Why it matches: Recommended by TMDB viewers · both comedy

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  13. Bill Burr: Drop Dead Years (2025)

    In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  14. Clear History (2013)

    Nathan Flomm, in order to avoid the humiliation of having missed out on a hugely successful business, assumes a new identity on Martha's Vineyard. He plots revenge when his former business partner moves to the same town.

    Why it matches: Recommended by TMDB viewers · both comedy

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  15. Ali Wong: Single Lady (2024)

    After a whirlwind couple of years, Ali Wong returns to the stage to dish on the highs, lows and surprises of dating post-divorce.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  16. The Wedding Year (2019)

    A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.

    Why it matches: Recommended by TMDB viewers · both comedy

  17. Me Time (2022)

    With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.

    Why it matches: Recommended by TMDB viewers · both comedy

  18. Duplex (2003)

    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!

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  19. Held Up (1999)

    What should have been a romantic getaway turns into one hilarious debacle after another when Michael's woman dumps him in the desert where he gets carjacked by a teenager and he is taken hostage in a stickup at the local Sip and Zip.

    Why it matches: Recommended by TMDB viewers · both comedy

  20. Driver's Ed (2026)

    A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this

Like Smoking Cuban Style and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like Smoking Cuban Style?

The closest matches to Smoking Cuban Style are Fun with Dick and Jane (1977), Chief Daddy 2: Going for Broke (2021) and Men in the City 2 (2011). Below are 17 more, each with the reason it matches.

What should I watch after Smoking Cuban Style?

Start with Fun with Dick and Jane (1977), the closest match to Smoking Cuban Style.

What is the highest-rated movie like Smoking Cuban Style?

Much Ado About Nothing (2013), rated 6.8/10 by 299 TMDB users.

What is the newest movie like Smoking Cuban Style?

Driver's Ed (2026) is the most recent release on this list.

Are there German movies like Smoking Cuban Style?

Yes: Men in the City 2 (2011), The Awakening of Motti Wolkenbruch (2018) and The Manny (2015).

How are movies similar to Smoking Cuban Style chosen?

First come films that Trakt’s viewers watch alongside Smoking Cuban Style, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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