Movies like I'm Skillful in Love and Pure Art (1999)
The best movies like I'm Skillful in Love and Pure Art (1999) are Bill Burr: Why Do I Do This? (2008), Hard to Die (1990) and What a Mess! (1995). If I'm Skillful in Love and Pure Art hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedLouis C.K.: Hilarious (2010)7.8/10 from 321 votes
- NewestRicky Gervais: Mortality (2025)Released 2025
Bill Burr: Why Do I Do This? (2008)
One of America's fastest-rising comedians, Bill Burr wields his razor-sharp wit with rare skill. In this brand-new stand-up performance, Bill takes aim at the stuff that drives us crazy, political correctness gone haywire, and girlfriends, or as he calls them: relentless psycho robots. A keenly observant social commentator, Bill Burr is also one of the funniest voices in comedy today.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisHard 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 thisWhat a Mess! (1995)
A Russian criminal steals a giant diamond from the Mafia, hides it, and suddenly runs into his unknown brothers; unexpected, absurd events with participation of the mob, doctors, musicians, Americans, militia, and gypsies ensue.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisShane 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 thisBill 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 thisGabriel 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 thisKidnapping, Caucasian Style (1967)
Shurik, a kind but naïve ethnography student, falls in love with the intelligent, athletic and beautiful All-Union Leninist Young Communist League member Nina. He has a rival in the wealthy comrade Saakhov, who concocts a kidnapping scheme to force Nina to marry him.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisRicky 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 thisHannibal Buress: Comedy Camisado (2016)
He's a kamikaze gambler. A one-arm cuddler. And if his fly is down, so be it. A night of sly riffs and slow burns.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisRussell Peters: Almost Famous (2016)
The comic comes home to Toronto to sound off on cultural quirks, furniture building and bathroom visits, revelling in all things ridiculously human.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJerry 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
Popcorn FlickMovies like thisTaylor Tomlinson: Quarter-Life Crisis (2020)
Comedian Taylor Tomlinson is halfway through her 20s — and she's over it. From dating losers to a failed engagement, she takes aim at her life choices.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisNikki Glaser: Someday You'll Die (2024)
Comedian and actress Nikki Glaser is back in her second HBO special, diving into a wide range of topics including why she doesn't want kids, the harsh realities of aging, her sexual fantasies and more.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisRicky Gervais: SuperNature (2022)
With his signature pitch-black sense of humor, Ricky Gervais takes the stage at the London Palladium in this provocative stand-up comedy special.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisClass 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
Popcorn FlickMovies like thisLouis 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 thisPeculiarities of the National Hunt (1995)
A Finn preparing a work on the Russian hunting traditions and customs, comes to Russia to collect materials and is invited to take part in a hunting party. His flamboyant companions include an Army general, with more than a passing resemblance to Aleksander Lebed, a police detective, local forest ranger (a devotee of Zen Buddhism) and some big-city types from St. Petersburg. Inevitably, their good intentions soon give way to endless drinking, visits to local farm girls and much else besides.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSincerely Louis C.K. (2020)
Louis C.K. muses on religion, terrorism, small towns, Florida, disabilities, dogs, Auschwitz, marriage, sex, vegans, and his personal sexual controversy, in a live performance from Washington, D.C.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisAdventures 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
Popcorn FlickMovies like thisRicky 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
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Frequently asked questions
What are the best movies like I'm Skillful in Love and Pure Art?
The closest matches to I'm Skillful in Love and Pure Art are Bill Burr: Why Do I Do This? (2008), Hard to Die (1990) and What a Mess! (1995). Below are 17 more, each with the reason it matches.
What should I watch after I'm Skillful in Love and Pure Art?
Start with Bill Burr: Why Do I Do This? (2008), the closest match to I'm Skillful in Love and Pure Art.
What is the highest-rated movie like I'm Skillful in Love and Pure Art?
Louis C.K.: Hilarious (2010), rated 7.8/10 by 321 TMDB users.
What is the newest movie like I'm Skillful in Love and Pure Art?
Ricky Gervais: Mortality (2025) is the most recent release on this list.
How are movies similar to I'm Skillful in Love and Pure Art chosen?
First come films that Trakt’s viewers watch alongside I'm Skillful in Love and Pure Art, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.