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Movies like Cheating with the Boss (2024)

The best movies like Cheating with the Boss (2024) are Dolemite Is My Name (2019), South Park (Not Suitable for Children) (2023) and Internal Affairs (1990). If Cheating with the Boss hooked you, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Dolemite Is My Name (2019)

    The story of Rudy Ray Moore, who created the iconic big screen pimp character Dolemite in the 1970s.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  2. South Park (Not Suitable for Children) (2023)

    After it's discovered that a teacher at South Park Elementary has an OnlyFans page, Randy is compelled to take a closer look at the seedy underbelly of the world of online influencers.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  3. Internal Affairs (1990)

    Keen young Raymold Avila joins the Internal Affairs Department of the Los Angeles police. He and partner Amy Wallace are soon looking closely at the activities of cop Dennis Peck whose financial holdings start to suggest something shady. Indeed Peck is involved in any number of dubious or downright criminal activities. He is also devious, a womaniser, and a clever manipulator, and he starts to turn his attention on Avila.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  4. Beyond the Valley of the Dolls (1970)

    An all-girl rock band moves to Hollywood in the hope of achieving success, only to fall into a whirlpool of wickedness and decadence.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  5. The Devil's Double (2011)

    A chilling vision of the House of Saddam Hussein comes to life through the eyes of the man who was forced to become the double of Hussein's sadistic son.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  6. QT8: The First Eight (2019)

    A detailed account of the life and artistic career of legendary filmmaker Quentin Tarantino, from his early days as a video club manager to the scandalous fall in disgrace of producer Harvey Weinstein. A story about how to shoot eight great movies and become an icon of modern pop culture.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  7. For Sama (2019)

    A love letter from a young mother to her daughter, the film tells the story of Waad al-Kateab’s life through five years of the uprising in Aleppo, Syria as she falls in love, gets married and gives birth to Sama, all while cataclysmic conflict rises around her. Her camera captures incredible stories of loss, laughter and survival as Waad wrestles with an impossible choice– whether or not to flee the city to protect her daughter’s life, when leaving means abandoning the struggle for freedom for which she has already sacrificed so much.

    Why it matches: Recommended by TMDB viewers

    Absolute CinemaMovies like this
  8. I.D. (1995)

    Four policemen go undercover and infiltrate a gang of football hooligans hoping to route out their leaders. For one of the four, the line between 'job' and 'yob' becomes more unclear as time passes . . .

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  9. Shame (2011)

    Brandon, a thirty-something man living in New York, eludes intimacy with women but feeds his deepest desires with a compulsive addiction to sex. When his younger sister temporarily moves into his apartment, stirring up bitter memories of their shared painful past, Brandon's life, like his fragile mind, gets out of control.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  10. Jackass 3D (2010)

    Johnny Knoxville, Bam Margera, Steve-O, Wee Man and the rest of their fearless and foolhardy friends take part in another round of outrageous pranks and stunts. In addition to standing in the path of a charging bull, launching themselves into the air and crashing through various objects, the guys perform in segments such as "Sweatsuit Cocktail," "Beehive Tetherball" and "Lamborghini Tooth Pull."

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  11. The Glorias (2020)

    An equal rights crusader, journalist and activist: Gloria Steinem embodies these and more. From her role in the revolutionary women's rights movement to her travels throughout the U.S. and around the world, Steinem has made an everlasting mark on modern history. A nontraditional chronicle of a trailblazing life.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  12. Auto Focus (2002)

    A successful TV star during the 1960s, former "Hogan's Heroes" actor Bob Crane projects a wholesome family-man image, but this front masks his persona as a sex addict who records and photographs his many encounters with women, often with the help of his seedy friend, John Henry Carpenter. This biographical drama reveals how Crane's double life takes its toll on him and his family, and ultimately contributes to his death.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  13. Fifty Shades of Grey (2015)

    When college senior Anastasia Steele steps in for her sick roommate to interview prominent businessman Christian Grey for their campus paper, little does she realize the path her life will take. Christian, as enigmatic as he is rich and powerful, finds himself strangely drawn to Ana, and she to him. Though sexually inexperienced, Ana plunges headlong into an affair -- and learns that Christian's true sexual proclivities push the boundaries of pain and pleasure.

    Why it matches: Recommended by TMDB viewers

  14. Shampoo (1975)

    On Election Day, 1968, irresponsible hairdresser and ladies' man George Roundy is too busy cutting hair and dealing with his girlfriends and mistress Felicia Karpf, whose husband Lester is having an affair with his ex-girlfriend Jackie.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  15. Nymphomaniac: Vol. I (2013)

    A man named Seligman finds a fainted wounded woman in an alley and he brings her home. She tells him that her name is Joe and that she is nymphomaniac. Joe tells her life and sexual experiences with hundreds of men since she was a young teenager while Seligman tells about his hobbies, such as fly fishing, reading about Fibonacci numbers or listening to organ music.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  16. Hard to Die (1990)

    While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series of killings six months previously, is at the bottom of the whole thing. Little do they know the real horror that they face in the end.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  17. Aileen Wuornos: The Selling of a Serial Killer (1992)

    In this documentary, filmmaker Nick Broomfield follows the saga of Aileen Wuornos, a prostitute who has been accused of committing a brutal series of murders. Broomfield conducts interviews with Wuornos herself, and his crew films her trial as well as her interactions with religious fanatic Arlene Pralle, who gives Wuornos dubious advice and legally adopts her. The cameras also roll as the accused's attorney ignores the case at hand to negotiate a deal to sell his client's story.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  18. Meet Monica Velour (2010)

    For Tobe, a nerdy, horny, frizzy-haired cineaste who doesn't quite fit in with the average contemporary teen, the pinnacle of womanhood is Monica Velour, a soft-core actress who reached the zenith of her career in the 1980s. When Tobe learns that his love idol is headlining hundreds of miles away at the Gentlemen's Petting Zoo in Indiana, he drives off with carefree glory, filled with the hope of meeting her.

    Why it matches: Recommended by TMDB viewers

  19. Never Back Down: Revolt (2021)

    An amateur fighter is lured by a trafficking syndicate specializing in elite underground fighting where her brutal captor forces her to fight or face certain death.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  20. Crimes of Passion (1984)

    Fashion designer Joanna Crane leads a double life. By night she is China Blue, a prostitute who's attracted the attention of a sexually frustrated private detective, and a psychopathic priest in possession of a murderous sex toy.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this

Like Cheating with the Boss and something else?

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

Frequently asked questions

What are the best movies like Cheating with the Boss?

The closest matches to Cheating with the Boss are Dolemite Is My Name (2019), South Park (Not Suitable for Children) (2023) and Internal Affairs (1990). Below are 17 more, each with the reason it matches.

What should I watch after Cheating with the Boss?

Start with Dolemite Is My Name (2019), the closest match to Cheating with the Boss.

What is the highest-rated movie like Cheating with the Boss?

For Sama (2019), rated 8.2/10 by 323 TMDB users.

What is the newest movie like Cheating with the Boss?

South Park (Not Suitable for Children) (2023) is the most recent release on this list.

Are there English movies like Cheating with the Boss?

Yes: Dolemite Is My Name (2019), South Park (Not Suitable for Children) (2023) and Internal Affairs (1990).

How are movies similar to Cheating with the Boss chosen?

First come films that Trakt’s viewers watch alongside Cheating with the Boss, 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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