Skip to content

Movies like Cougar 101 (2009)

The best movies like Cougar 101 (2009) are Pretty Persuasion (2005), Shane Gillis: Beautiful Dogs (2023) and Hard to Die (1990). If Cougar 101 hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Pretty Persuasion (2005)

    A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.

    Why it matches: Recommended by TMDB viewers · both comedy

  2. 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
  3. 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 · both comedy

    Popcorn FlickMovies like this
  4. 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
  5. Ricky Gervais: Mortality (2025)

    Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  6. Ricky Gervais: Armageddon (2023)

    Ricky Gervais dishes out controversial takes on political correctness and oversensitivity in a taboo-busting comedy special about the end of humanity.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  7. Jimmy Carr: Natural Born Killer (2024)

    Jimmy Carr refutes the idea that you can't joke about anything these days with his edgy takes on gun control, religion, cancel culture and consent.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  8. 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
  9. 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 · both comedy

    Worth the HypeMovies like this
  10. 68 Kill (2017)

    Chip's problem is that he can't say no to beautiful women. This weakness gets him into a world of trouble when he agrees to help his girlfriend steal $68,000.

    Why it matches: Recommended by TMDB viewers · both comedy

  11. Desperate Living (1977)

    After killing her husband, Peggy Gravel and her murderous maid Grizelda wind up in the crazy town of Mortville, where Queen Carlotta presides over a sleazy collection of misfits.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  12. Jimmy Carr: Telling Jokes (2009)

    Jimmy Carr delivers more of his cynical take on life's little absurdities in his trademark deadpan style in this live stand-up release. Jimmy unleashes his rapid-fire joke-telling and razor-sharp wit on topics ranging from religion and sex, to bullying and political correctness. Those brave enough to heckle are quickly put in their place by an array of colourful if brutal put-downs.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  13. Jeff Dunham: Arguing with Myself (2006)

    A recorded live performance of ventriloquist Jeff Dunham portrays a comedian whose revival of an old-fashioned art has made ventriloquism more relevant to modern societal concerns. Starring his six main characters, from Bubba Jay, a Nascar-obsessed hick, to Peanut, a flamboyant gay monkey, Dunham’s puppets have dirty but inoffensive senses of humor that mock the American Dream.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  14. Dave Chappelle: The Unstoppable... (2025)

    Facing a world gone sideways, comedy icon Dave Chappelle delivers bold truths and potent punchlines in this no-holds-barred special.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  15. Goltzius & the Pelican Company (2012)

    Hendrik Goltzius, a late-16th-century Dutch printer and engraver of erotic prints, seduces the Margrave of Alsace into paying for a printing press to make and publish illustrated books.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  16. The Horse's Mouth (1958)

    Gulley Jimson is a boorish aging artist recently released from prison. A swindler in search of his next art project, he hunkers down in the penthouse of would-be patrons the Beeders while they go on an extended vacation; he paints a mural on their wall, pawns their valuables and, along with the sculptor Abel, inadvertently smashes a large hole in their floor. Jimson's next project is an even larger wall in an abandoned church.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  17. Cotton Comes to Harlem (1970)

    Harlem's African-American population is being ripped off by the Rev. Deke O'Malley, who dishonestly claims that small donations will secure parcels of land in Africa. When New York City police officers Gravedigger Jones and Coffin Ed Johnson look into O'Malley's scam, they learn that the cash is being smuggled inside a bale of cotton. However, the police, O'Malley, and lots of others find themselves scrambling when the money goes missing.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  18. The Sweet East (2023)

    A picaresque journey through contemporary America, undertaken by a young woman granted access to the strange sects and cults that proliferate in this country by a series of gatekeepers eager to win her over.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  19. Who Is Cletis Tout? (2001)

    With a hitman’s gun aimed at him, Finch tells the story of how he broke out of jail, fell in love, and took the identity of a man wanted by the Mafia.

    Why it matches: Recommended by TMDB viewers · both comedy

  20. The Overnight (2015)

    Alex, Emily, and their son, RJ, are new to Los Angeles. A chance meeting at the park introduces them to the mysterious Kurt, Charlotte, and Max. A family “playdate” becomes increasingly interesting as the night goes on.

    Why it matches: Recommended by TMDB viewers · both comedy

  21. Arisan Brondong (2010)

    Geng socialite mother; Lolita was a widow who became entrepreneurs due to expensive boutiques treasure Gono-gini ex-ex-husband, Anis rather an idiot, and Uut fat, often hold joint gathering costly. By the time the three get together, the mortal enemy of Lolita, Misye, while gathering brought a popcorn (the term to refer to youth aged bear) named Erik. Misye gaze is believed to be a challenge for Lolita, which eventually terkompori and with Anis and Uut, holding auditions looking for popcorn at the shop.

    Why it matches: Similar story and style · both comedy

  22. MILF (2018)

    Three childhood friends - Elise, Sonia and Cecile - leave for a summer in the South of France to help clear Cecile’s holiday house before it is put up for sale. There, they soon become the prime targets of three horny young men, for whom these single forty-year-old women are much more attractive than girls their age.

    Why it matches: Similar story and style · both comedy

  23. Cougar Hunting (2011)

    Tells the tale of three buddies in their 20's whose love-lives are in shambles. They go to Aspen to pursue the booming trend of dating cougars: hot older women who prey on hot young guys.

    Why it matches: Similar story and style · both comedy

  24. Cougar School (2009)

    Karen leaves Zack to go on the hunt with her Step Mother for wealthy younger men.

    Why it matches: Similar story and style · both comedy

  25. Female Company (1999)

    High society women of a small Greek town try everything to have sex with the first male they can find.

    Why it matches: Similar story and style · both comedy

  26. American Reunion (2012)

    The characters we met a little more than a decade ago return to East Great Falls for their high school reunion. In one long-overdue weekend, they will discover what has changed, who hasn’t, and that time and distance can’t break the bonds of friendship.

    Why it matches: Similar story and style · both comedy

    Popcorn FlickMovies like this
  27. RATS! (2025)

    In a surreal small‑town version of 2007 Texas, a young graffiti artist lands in jail and is coerced into spying on his cousin—suspected by an unhinged cop of dealing nuclear weapons. What follows is a frenetic, gross‑humored ride through conspiracy, over-the-top characters, and chaotic counterculture.

    Why it matches: Similar story and style · both comedy

  28. Spotless (2024)

    Gloria sneaks into a stranger's house and examines every corner until she finds what she is looking for. The excitement of the dirt and chaos around her produces a rhythmic orgasm.

    Why it matches: Similar story and style · both comedy

  29. Tough Luck (2026)

    ​Arrested by mistake and mistaken for France’s most wanted man, Serge Martin, a peaceful retiree, becomes the target of the media. Caught up in a never-ending whirlwind, he’ll do everything he can to prove his innocence and get his life back… if that’s even possible!

    Why it matches: Similar story and style · both comedy

  30. Tortoise Gang (TBA)

    An interviewer is tasked to interview two men who may have connections to the “Tortoise Gang”, a gang that uses tortoises to steal valuable treasure

    Why it matches: Similar story and style · both comedy

Like Cougar 101 and something else?

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

Frequently asked questions

What are the best movies like Cougar 101?

The closest matches to Cougar 101 are Pretty Persuasion (2005), Shane Gillis: Beautiful Dogs (2023) and Hard to Die (1990). Below are 27 more, each with the reason it matches.

What should I watch after Cougar 101?

Start with Pretty Persuasion (2005), the closest match to Cougar 101.

What is the highest-rated movie like Cougar 101?

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

What is the newest movie like Cougar 101?

Tough Luck (2026) is the most recent release on this list.

Are there English movies like Cougar 101?

Yes: Pretty Persuasion (2005), Shane Gillis: Beautiful Dogs (2023) and Hard to Die (1990).

How are movies similar to Cougar 101 chosen?

First come films that Trakt’s viewers watch alongside Cougar 101, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

↑ ↓ to move · Enter to open · Full search page