Movies like Kissing Jessica Stein (2002)
The best movies like Kissing Jessica Stein (2002) are Ali Wong: Single Lady (2024), Driver's Ed (2026) and Die, Mommie, Die! (2003). If Kissing Jessica Stein hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedBo Burnham: Make Happy (2016)8.0/10 from 460 votes
- NewestDating Sucks (2026)Released 2026
Ali Wong: Single Lady (2024)
After a whirlwind couple of years, Ali Wong returns to the stage to dish on the highs, lows and surprises of dating post-divorce.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDriver'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
Popcorn FlickMovies like thisDie, Mommie, Die! (2003)
Angela Arden is a washed up, has-been singing star who is trapped in a hateful marriage to film producer Sol Sussman. In an attempt to escape her marriage so that she can be with a hunky layabout, she poisons her husband. However, Angela's manipulative daughter, gay son and alcoholic maid are not going to make it easy for her.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAdam 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
Popcorn FlickMovies 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 thisThe Jerk Theory (2009)
An aspiring recording artist, Adam, is burned by a bad relationship experience and decides that if women won't respond to the "nice guy" then he'll be "the jerk." This is wildly successful with meaningless relationships, but when Adam meets and falls for Molly, who doesn't fall for his jerk routine, Adam is forced to reconsider his dating philosophy.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisThe Nowhere Inn (2021)
When St. Vincent sets out to make a documentary about her music, the goal is to both reveal and revel in the unadorned truth behind her on-stage persona. But when she hires a close friend to direct, notions of reality, identity, and authenticity grow increasingly distorted and bizarre.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisMike Birbiglia: The New One (2019)
Comedian Mike Birbiglia hits Broadway with a hilarious yet profound one-man show that recounts his emotional and physical journey to parenthood.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe Wedding Year (2019)
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies 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 thisGoltzius & 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 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 thisThe Ritz (1976)
To escape from a mobster, businessman Gaetano Proclo orders a cab driver to take him to a place where he can't be found. Unfortunately for Gaetano, the place turns out to be a gay bathhouse.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisA Night at the Opera (1935)
The Marx Brothers take on high society and the opera world to bring two lovers together. A sly business manager and two wacky friends of two opera singers help them achieve success while humiliating their stuffy and snobbish enemies.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisBo Burnham: Make Happy (2016)
Combining his trademark wit and self-deprecating humor with original music, Bo Burnham offers up his unique twist on life in this stand-up special about life, death, sexuality, hypocrisy, mental illness and Pringles cans.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies like thisMichelle Wolf: Joke Show (2019)
Comedian Michelle Wolf takes on outrage culture, massages, childbirth, feminism and much more (like otters) in a stand-up special from New York City.
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 thisSarah Silverman: Jesus Is Magic (2005)
Sarah Silverman appears before an audience in Los Angeles with several sketches, taped outside the theater, intercut into the stand-up performance. Themes include race, sex, and religion. Her comic persona is a self-centered hipster, brash and clueless about her political incorrectness. A handful of musical numbers punctuate the performance.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSarah Silverman: A Speck of Dust (2017)
In her first comedy special post-health scare, Sarah Silverman shares a mix of fun facts, sad truths and yeah-she-just-went-there moments.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAdam Sandler: 100% Fresh (2018)
Adam Sandler takes his comical musical musings back out on the road, from comedy clubs to concert halls to one very unsuspecting subway station.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisLiving It Up (1954)
Homer Flagg is a railroad worker in the small New Mexico town of Desert Hole. One day, he finds an abandoned automobile at an old atomic proving ground. His doctor and best friend, Steve Harris, diagnoses him with radiation poisoning and gives Homer three weeks to live. A big city reporter hears of Homer's plight and convinces her editor to provide an all-expenses paid trip to New York.
Why it matches: Similar story and style · both comedy
Man's Favorite Sport? (1964)
Roger Willoughby is a renowned fishing expert, who, unbeknownst to his friends, co-workers, or boss, has never cast a line in his life. One day, he crosses paths with Abigail Paige, a sweetly annoying girl who has just badgered his boss into signing Roger up for an annual fishing tournament.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisOnce Around (1991)
A struggling woman finds unexpected love with a charismatic older salesman at a real estate seminar. Their passionate relationship clashes with the values of her family, particularly her father.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisLife As We Know It (2010)
After a disastrous first date for caterer Holly and network sports director Messer, all they have in common is a dislike for each other and their love for their goddaughter Sophie. But when they suddenly become all Sophie has in this world, Holly and Messer must set their differences aside. Juggling careers and social calendars, they'll have to find common ground while living under the same roof.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisDating Sucks (2026)
A vampiress navigates the turmoils of modern dating.
Why it matches: Similar story and style · both comedy
The Good Guy (2009)
Ambitious young Manhattanite and urban conservationist Beth wants it all: a good job, good friends, and a good guy to share the city with. Of course that last one is often the trickiest of all. Beth falls hard for Tommy, a sexy, young Wall Street hot-shot. But just as everything seems to be falling into place, complications arise in the form of Tommy's sensitive and handsome co-worker Daniel. Beth soon learns that the game of love in the big city is a lot like Wall Street -- high risk, high reward and everybody has an angle.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisJoni's Promise (2005)
A film delivery man promises a beautiful young woman to deliver a film reel on time to a movie theater, but the the whole city seems to conspire against him.
Why it matches: Similar story and style · both comedy
Coffee House Chronicles: The Movie (2016)
This film, based on the web series, features nine vignettes in the lives of LGBT people as they date and hook up in Los Angeles.
Why it matches: Similar story and style · both comedy
Dinner at Eight (1933)
An ambitious New York socialite plans an extravagant dinner party as her businessman husband, Oliver, contends with financial woes, causing a lot of tension between the couple. Meanwhile, their high-society friends and associates, including the gruff Dan Packard and his sultry spouse, Kitty, contend with their own entanglements, leading to revelations at the much-anticipated dinner.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisAnd Then Came Lola (2009)
A talented, but distracted photographer, Lola, on the verge of success in both love and work, could lose it all if she doesn't make it to a crucial meeting on time. But, as usual, Lola is late. With her job and girlfriend on the line, she has three chances to make it right. In a desperate race through the streets and back rooms of San Francisco, time grows short-will Lola make it? Will she come at all? With a pop sensibility that mixes live action, animation and still photography, And Then Came Lola explores love's age old question in a fresh new way, "If you try, try again, will you finally get it right?" (Written by M. Siler and E. Seidler)
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like Kissing Jessica Stein?
The closest matches to Kissing Jessica Stein are Ali Wong: Single Lady (2024), Driver's Ed (2026) and Die, Mommie, Die! (2003). Below are 27 more, each with the reason it matches.
What should I watch after Kissing Jessica Stein?
Start with Ali Wong: Single Lady (2024), the closest match to Kissing Jessica Stein.
What is the highest-rated movie like Kissing Jessica Stein?
Bo Burnham: Make Happy (2016), rated 8.0/10 by 460 TMDB users.
What is the newest movie like Kissing Jessica Stein?
Dating Sucks (2026) is the most recent release on this list.
Are there English movies like Kissing Jessica Stein?
Yes: Ali Wong: Single Lady (2024), Driver's Ed (2026) and Die, Mommie, Die! (2003).
How are movies similar to Kissing Jessica Stein chosen?
First come films that Trakt’s viewers watch alongside Kissing Jessica Stein, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.