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Comedies of 1995 to 1999

236 articles

10 Things I Hate About You

10 Things I Hate About You (1999) is a Touchstone teen romantic comedy directed by Gil Junger, loosely adapting Shakespeare's The Taming of the Shrew, starring Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, and Larisa Oleynik at fictional Padua High School.

200 Cigarettes

200 Cigarettes (1999), Risa Bramon Garcia's ensemble comedy written by Shana Larsen, follows twenty-somethings through New Year's Eve 1981 in New York's East Village toward Monica's party; MTV Films production starring Afflecks, Hudson, Love, Ricci, Rudd.

8½ Women (8 1/2の女たち)

8½ Women (8 1/2の女たち) is Peter Greenaway's 1999 comedy-drama, in Cannes competition, about a widowed Geneva tycoon and his son keeping eight and a half concubines after watching Fellini's 8½; it earned $424,123 and mixed-to-negative reviews.

A Life Less Ordinary

A Life Less Ordinary is a 1997 British romantic black comedy by Danny Boyle, in which Ewan McGregor kidnaps Cameron Diaz and angels push them into love.

A Man Among Men

A Man Among Men, released in Korea as Jincha sanai and in Australia as True Man, is a 1999 South Korean road comedy directed by Hun-Su Park, starring Kwon Hae-hyo and Mi-kyeong Seo.

A Simple Wish

A Simple Wish is a 1997 American family fantasy-comedy directed by Michael Ritchie. It stars Martin Short as the first male fairy godmother, alongside Mara Wilson.

A Thin Line Between Love and Hate

A Thin Line Between Love and Hate is a 1996 American romantic comedy-thriller, Martin Lawrence's directorial debut, starring him as a womanizing Los Angeles club promoter.

A Walk in the Clouds

A Walk in the Clouds is a 1995 romantic drama directed by Alfonso Arau, remaking the Italian film Quattro passi fra le nuvole; Keanu Reeves poses as a pregnant woman's husband in postwar Napa Valley, grossing $50 million domestically.

Adulthood (2025 film)

Adulthood, aka The Adults, is a 2025 American dark comedy crime film directed by Alex Winter, starring Josh Gad and Kaya Scodelario as siblings who find a corpse in their parents' basement; it premiered at TIFF 2025 and streams via Republic Pictures.

Airbag (1997 film)

Airbag (1997) is a Spanish black-comedy road movie by Juanma Bajo Ulloa, written with Karra Elejalde and Fernando Guillen Cuervo, about three friends recovering a lost engagement ring; it was Spain's top-grossing film of 1997 and won two Goya Awards.

Angus (film)

Angus (1995) is an American teen comedy-drama directed by Patrick Read Johnson, adapted from Chris Crutcher's short story, starring Charlie Talbert, Kathy Bates, George C. Scott, and James Van Der Beek.

Anywhere but Here (film)

Anywhere but Here (1999) is a Wayne Wang comedy-drama adapted by Alvin Sargent from Mona Simpson's 1986 novel, starring Susan Sarandon and Natalie Portman as a mother and daughter who move from Wisconsin to Beverly Hills; 20th Century Fox, Metascore 59, $18.7M gross.

April Story (四月物語)

April Story (四月物語) is a 1998 Japanese youth romance film by Shunji Iwai, starring Takako Matsu in her film lead debut as Uzuki Nireno, a Hokkaido student who moves to Tokyo for university, secretly following her high school crush Yamazaki; 67 minutes, Rockwell Eyes, released March 14, 1998.

Art Museum by the Zoo (미술관 옆 동물원)

Art Museum by the Zoo (미술관 옆 동물원) is Lee Jeong-hyang's 1998 South Korean romantic comedy debut, 108 minutes, starring Shim Eun-ha and Lee Sung-jae as cohabiting strangers who co-write a screenplay; 413,216 admissions and multiple 1999 awards.

As Good as It Gets

As Good as It Gets is a 1997 American romantic comedy-drama directed by James L. Brooks, starring Jack Nicholson as an obsessive-compulsive novelist and Helen Hunt as a waitress.

Babe (film)

Babe (1995), Chris Noonan's Australian comedy-drama adapted from Dick King-Smith's The Sheep-Pig, about a piglet who herds sheep; won the Best Visual Effects Oscar, earned $250 million, used 970 trained animals.

Baby Geniuses

Baby Geniuses is a 1999 American family comedy directed by Bob Clark and starring Kathleen Turner and Christopher Lloyd, in which scientists try to decode the secret language of babies.

Bathing (1999 film)

Bathing, internationally released as Shower (洗澡, Xizao), is Zhang Yang's 1999 Chinese comedy-drama about a Beijing bathhouse, father-son bonds, and demolition-driven modernization; it won FIPRESCI at Toronto and the Golden Alexander at Thessaloniki.

Beautiful Girls (film)

Beautiful Girls is a 1996 American comedy-drama-romance directed by Ted Demme, written by Scott Rosenberg, starring Timothy Hutton, Matt Dillon, and Natalie Portman. Set in Knight's Ridge, Massachusetts, it follows friends at a high school reunion; it earned $10,597,759 in the US.

Beautiful Mother

Beautiful Mother (Belle maman) is a 1999 French romantic comedy directed by Gabriel Aghion, starring Catherine Deneuve, Vincent Lindon, and Mathilde Seigner, about a groom who falls for his mother-in-law on his wedding day.

Before Sunrise

Before Sunrise (1995) is Richard Linklater's romance starring Ethan Hawke and Julie Delpy as strangers who spend one night talking through Vienna; first of the Before trilogy, Silver Bear winner, National Film Registry inductee.

Bend Over Boyfriend 2

Bend Over Boyfriend 2: More Rockin', Less Talkin' is a 1999 American instructional pornographic video by Shar Rednour and Jackie Strano (S.I.R. Video), sequel to Bend Over Boyfriend, depicting women using strap-on dildos on men (pegging).

Better Than Chocolate

Better Than Chocolate is a 1999 Canadian lesbian romantic comedy directed by Anne Wheeler, written by Peggy Thompson, starring Karyn Dwyer, Christina Cox, and Wendy Crewson; its Vancouver bookstore subplot draws on the Little Sister's censorship case.

Beverly Hills Ninja

Beverly Hills Ninja is a 1997 American slapstick comedy directed by Dennis Dugan, starring Chris Farley as a clumsy ninja investigating a Beverly Hills murder.

Big Daddy (1999 film)

Big Daddy is a 1999 American comedy directed by Dennis Dugan, starring Adam Sandler as a lazy law school graduate who adopts a five-year-old boy to impress his girlfriend.

Big Night

Big Night (1996) is an American independent comedy-drama co-directed by Stanley Tucci and Campbell Scott, about Italian immigrant brothers whose New Jersey restaurant, Paradise, stakes its survival on a banquet for Louis Prima; it won Sundance's screenwriting award.

Billy Madison

Billy Madison is a 1995 American comedy starring Adam Sandler and directed by Tamra Davis. The film follows a spoiled heir repeating school to inherit a hotel fortune.

Bio-Dome

Bio-Dome is a 1996 American comedy directed by Jason Bloom, starring Pauly Shore and Stephen Baldwin as slackers sealed inside an ecological research facility for a year.

Black Cat, White Cat

Black Cat, White Cat (Crna mačka, beli mačor) is Emir Kusturica's 1998 Romani comedy set on the Danube, winner of the Venice Silver Lion for Best Director and his follow-up to Underground.

Black Sheep (1996 film)

Black Sheep is a 1996 American buddy comedy directed by Penelope Spheeris, starring Chris Farley and David Spade in their second film after Tommy Boy; it opened at number one.