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Movies like Road to Bob (2019)

The best movies like Road to Bob (2019) are Tommy Boy (1995), Iliza Shlesinger: Freezing Hot (2015) and Hollywood or Bust (1956). If Road to Bob hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Tommy Boy (1995)

    To save the family business, two ne’er-do-well traveling salesmen hit the road with disastrously funny consequences.

    Why it matches: Recommended by TMDB viewers · both comedy

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  2. Iliza Shlesinger: Freezing Hot (2015)

    Smart and brazen comedian Iliza Shlesinger shares her unflinchingly honest observations on the differences between men and women. Filled with hashtag-able catch phrases, this is a laugh-out-loud revelation exposing some of women’s best kept - and ugliest - secrets, including truths about first date attire, fantasy break-ups and the tireless pursuit of not being cold while still looking hot.

    Why it matches: Recommended by TMDB viewers · both comedy

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  3. Hollywood or Bust (1956)

    The last movie with Jerry Lewis and Dean Martin together, is a satire of the life in Hollywood. Steve Wiley is a deceiver who cheats Malcolm Smith when he wins a car, claiming that he won it too. Trying to steal the car, Steve tells Malcolm that he lives in Hollywood, next to Anita Ekberg's. When Malcom hears that, they both set out for Hollywood and the adventure begins...

    Why it matches: Recommended by TMDB viewers · both comedy

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  4. 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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  5. The Rutles: All You Need Is Cash (1978)

    The story of the rise and fall of the Pre-Fab Four.

    Why it matches: Recommended by TMDB viewers · both comedy

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  6. Gabriel Iglesias: Hot and Fluffy (2007)

    Gabriel Iglesias is one of the fastest-rising comics today! With his unique brand of humor, lovable stage presence and wide range of voices and impressions, it's no wonder that he already has a huge fan following. Now you can see Comedy Central's "Comic of the Year" in his sold-out performance at the historic Fox Theatre in Bakersfield, California!

    Why it matches: Recommended by TMDB viewers · both comedy

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  7. The Ladies Man (1961)

    After his girl leaves him for someone else, Herbert gets really depressed and starts searching for a job. He finally finds one in a big house which is inhabited by many, many women. Can he live in the same home with all these females?

    Why it matches: Recommended by TMDB viewers · both comedy

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  8. Ricky Gervais: Out of England 2 (2010)

    The comic performs at the Chicago Theatre.

    Why it matches: Recommended by TMDB viewers · both comedy

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  9. Robot Chicken: Star Wars (2007)

    A series of 30 sketches, following the hilarious antics of various characters from a galaxy, far, far away.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  10. Louis C.K.: Hilarious (2010)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  11. Kevin Hart: Laugh at My Pain (2011)

    Experience the show that quickly became a national phenomenon. Get an up-close and personal look at Kevin back in Philly where he began his journey to become one of the funniest comedians of all time.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  12. Pups Alone (2021)

    After receiving an exciting new job opportunity at a cutting edge Pet Invention company, Robert, his teenage daughter Jenna and their trusty and special border collie Charlie make the move to the new neighborhood, right before Christmas. Upon arriving, Robert meets his gorgeous next door neighbor Holly, and her sassy and spunky border collie Gidget. Before the sparks can fly, they are set upon my Robert’s conniving and obnoxious next door neighbor and project manager Victor, his neighborhood bully bulldog “Vinnie P” and the sycophantic sidekick Chihuahua “Jose”.

    Why it matches: Recommended by TMDB viewers · both comedy

  13. 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

  14. Jerry Seinfeld: 23 Hours to Kill (2020)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

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  15. A Song Is Born (1948)

    The story of seven scholars in search of an expert to teach them about swing music. They seem to have found the perfect candidate in winsome nightclub singer Honey Swanson. But Honey's gangster boyfriend doesn't want to give her up.

    Why it matches: Recommended by TMDB viewers · both comedy

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  16. LEGO Marvel Avengers: Mission Demolition (2024)

    A young, aspiring hero and superhero fan inadvertently unleashes a powerful new villain looking to rid the world of the Avengers.

    Why it matches: Recommended by TMDB viewers · both comedy

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  17. Adventures in Public School (2018)

    A socially-awkward, home-schooled kid forces his way into public school against his suffocating, but loving, mother's wishes.

    Why it matches: Recommended by TMDB viewers · both comedy

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  18. Chris Rock: Tamborine (2018)

    Chris Rock takes the stage for his first comedy special in 10 years, filled with searing observations on fatherhood, infidelity and American politics.

    Why it matches: Recommended by TMDB viewers · both comedy

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  19. Heavy Metal Mater (2010)

    Mater and Lightning McQueen are ready to rock! When Mater's garage band, Mater and the Gas Caps, records a hit song, Mater becomes a rock legend. Then Lightning joins Mater's band for the rock concert of the century!

    Why it matches: Recommended by TMDB viewers · both comedy

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  20. Katt Williams: The Pimp Chronicles Pt. 1 (2006)

    Comedian Katt Williams (aka Money Mike) showcases his laugh out loud comedic talents in his first ever HBO stand-up comedy DVD taped in front of a live audience. A native of Cincinnati, Ohio, Williams worked his way up the comedy club ladder before landing key television and film roles that displayed his flashy, sassy, streetwise style.

    Why it matches: Recommended by TMDB viewers · both comedy

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Like Road to Bob and something else?

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

Frequently asked questions

What are the best movies like Road to Bob?

The closest matches to Road to Bob are Tommy Boy (1995), Iliza Shlesinger: Freezing Hot (2015) and Hollywood or Bust (1956). Below are 17 more, each with the reason it matches.

What should I watch after Road to Bob?

Start with Tommy Boy (1995), the closest match to Road to Bob.

What is the highest-rated movie like Road to Bob?

Louis C.K.: Hilarious (2010), rated 7.8/10 by 321 TMDB users.

What is the newest movie like Road to Bob?

LEGO Marvel Avengers: Mission Demolition (2024) is the most recent release on this list.

Are there English movies like Road to Bob?

Yes: Tommy Boy (1995), Iliza Shlesinger: Freezing Hot (2015) and Hollywood or Bust (1956).

How are movies similar to Road to Bob chosen?

First come films that Trakt’s viewers watch alongside Road to Bob, 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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