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Movies like His Luckless Love (1915)

The best movies like His Luckless Love (1915) are Adam Sandler: Love You (2024), American Dreamer (2022) and Bill Burr: Drop Dead Years (2025). If His Luckless Love hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Adam Sandler: Love You (2024)

    Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.

    Why it matches: Recommended by TMDB viewers · both comedy

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  2. American Dreamer (2022)

    In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.

    Why it matches: Recommended by TMDB viewers · both comedy

  3. 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
  4. Louis C.K.: Ridiculous (2026)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

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  5. The Hangover Part III (2013)

    This time, there's no wedding. No bachelor party. What could go wrong, right? But when the Wolfpack hits the road, all bets are off.

    Why it matches: Recommended by TMDB viewers · both comedy

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  6. Louis C.K.: Oh My God (2013)

    Filmed at the Celebrity Theatre in Phoenix, AZ on February 15th and 16th, 2013, Oh My God is Louis C.K.'s fifth stand-up special, his first for HBO since 2007's Shameless, and his first since winning a Emmy Award for writing on his acclaimed show on FX, Louie. Performed in the round in front of a live audience, he discusses such topics as the food chain, animals, divorce, strange anecdotes, broken morality, murder and mortality.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  7. The Distinguished Gentleman (1992)

    A Florida con man uses the recent death of the long time Congressman from his district, who he just happens to share a last name with, to get elected to his version of paradise, the U.S. Congress, where the money flows from lobbyists.

    Why it matches: Recommended by TMDB viewers · both comedy

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  8. Taking Care of Business (1990)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

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  9. Eddie Murphy Raw (1987)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  10. 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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  11. Oscar (1991)

    Angelo "Snaps" Provolone made his dying father a promise on his deathbed: he would leave the world of crime and become an honest businessman. Despite having no experience in making money in a legal fashion, Snaps sets about to keep his promise.

    Why it matches: Recommended by TMDB viewers · both comedy

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  12. 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

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  13. Jimmy O. Yang: Good Deal (2020)

    In his debut standup special, Good Deal, Jimmy will tell you all about his take on Asian representation, how he learned to speak English from rap videos, dating tall women, and pursuing his dreams only to disappoint his old school Chinese parents. From assimilation to representation, Jimmy O. Yang delivers an absolutely hilarious hour of comedy in Good Deal.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  14. Sarah Silverman: We Are Miracles (2013)

    In her first-ever HBO solo special, Sarah Silverman takes the stage for an evening of adults-only stand-up comedy. Taped live in front of an intimate audience of 39 fans at Largo, a music and comedy club in Los Angeles, Sarah Silverman: We Are Miracles features Silverman taking aim at such subjects as cell-phone porn, crazy religions, specialty deodorants, terrible roommates, eyebrow waxing, her 19-year-old dog, Obama and Republicans, having babies, Pixar movies, the miracle of existence, and more.

    Why it matches: Recommended by TMDB viewers · both comedy

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  15. 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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  16. Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)

    Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  17. Easy Money (1983)

    To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.

    Why it matches: Recommended by TMDB viewers · both comedy

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  18. Chris Rock: Selective Outrage (2023)

    Chris Rock delivers an electric stand-up set on non-racist yoga pants, spoiling his kids, the Kardashians and his thoughts on the Will Smith fiasco.

    Why it matches: Recommended by TMDB viewers · both comedy

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  19. Dave Chappelle: The Closer (2021)

    As he closes out his slate of comedy specials, Dave takes the stage to try and set the record straight — and get a few things off his chest.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  20. Chris Rock: Kill the Messenger (2008)

    An HBO special edited from three performances from Chris Rock's 2008 comedy tour: London (dark suit, dark shirt), Johannesburg (black suit, white shirt) and New York (shiny jacket). Topics include the ongoing presidential campaign, the possibility of a black president, George W. Bush, gas prices, low-paid jobs, ringtones and bottled water, sex, relationships and the correct use of the n-word

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this

Like His Luckless Love and something else?

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

Frequently asked questions

What are the best movies like His Luckless Love?

The closest matches to His Luckless Love are Adam Sandler: Love You (2024), American Dreamer (2022) and Bill Burr: Drop Dead Years (2025). Below are 17 more, each with the reason it matches.

What should I watch after His Luckless Love?

Start with Adam Sandler: Love You (2024), the closest match to His Luckless Love.

What is the highest-rated movie like His Luckless Love?

Louis C.K.: Oh My God (2013), rated 7.6/10 by 229 TMDB users.

What is the newest movie like His Luckless Love?

Louis C.K.: Ridiculous (2026) is the most recent release on this list.

Are there English movies like His Luckless Love?

Yes: Adam Sandler: Love You (2024), American Dreamer (2022) and Bill Burr: Drop Dead Years (2025).

How are movies similar to His Luckless Love chosen?

First come films that Trakt’s viewers watch alongside His Luckless Love, 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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