Movies Like Kissing Jessica Stein

If you liked Kissing Jessica Stein (2002), a comedy movie directed by Charles Herman-Wurmfeld, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Die, Mommie, Die! (2003)
★ 6.6/10Also comedy
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…
2
Driver's Ed (2026)
★ 6.9/10Also comedy
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.
3
Adam Sandler: Love You (2024)
★ 6.3/10Also comedy
Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.
4
Hard to Die (1990)
★ 6/10Also comedy
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…
5
Ali Wong: Single Lady (2024)
★ 6.4/10Also comedy
After a whirlwind couple of years, Ali Wong returns to the stage to dish on the highs, lows and surprises of dating post-divorce.
6
The Wedding Year (2019)
★ 5.9/10Also comedy
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.
7
Adam Sandler: 100% Fresh (2018)
★ 7.1/10Also comedy
Adam Sandler takes his comical musical musings back out on the road, from comedy clubs to concert halls to one very unsuspecting subway station.
8
A Night at the Opera (1935)
★ 7.4/10Also comedy
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…
9
Sarah Silverman: Jesus Is Magic (2005)
★ 6.4/10Also comedy
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…
10
Goltzius & the Pelican Company (2012)
★ 6.1/10Also comedy
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.
11
Jim Jefferies: Intolerant (2020)
★ 7.1/10Also comedy
Between scenes from an excruciating date, Jim Jefferies digs into generational differences, his own bad habits and the shifting boundaries in comedy.
12
The Ritz (1976)
★ 6/10Also comedy
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.
13
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
14
Desperately Seeking Susan (1985)
★ 6.1/10Also comedy
A bored New Jersey suburban housewife's fascination with a free-spirited woman she has read about in the personal columns leads to her being mistaken for the woman herself and into a chaotic adventure of amnesia and…
15
Ladies First (2026)
★ 6/10Also comedy
An arrogant but charismatic ladies' man finds his life of money, power and casual flings upended when he wakes up in a parallel world dominated by women.
16
The Nowhere Inn (2021)
★ 5.9/10Also comedy
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…
17
Like a Boss (2020)
★ 6.2/10Also comedy
Two female friends with very different ideals decide to start a beauty company together. One is more practical, while the other wants to earn her fortune and live a lavish lifestyle.
18
Sarah Silverman: A Speck of Dust (2017)
★ 6.8/10Also comedy
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.
19
Bo Burnham: Make Happy (2016)
★ 8/10Also comedy
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…
20
Psycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer (2025)
★ 6.8/10Also comedy
A struggling writer in the midst of a divorce befriends a retired serial killer who incidentally becomes his marriage counselor by day, and killing counselor for his next book by night.