14. If These Walls Could Talk 2 (2000)
Starring: Vanessa Redgrave, Chloë Sevigny, Michelle Williams, Sharon Stone, Ellen DeGeneres, Natasha Lyonne Directors: Jane Anderson, Martha Coolidge, Anne Heche
HBO’s TV movie featured an all-star cast in vignettes of lesbian life throughout three different decades. Dealing with ideas of life-long partnership ignored by one’s family, conceiving a child, attempts to become part of a feminist party and other political statements, If These Walls Could Talk 2 is an important piece that people could still learn from, 12 years later. It won Vanessa Redgrave an Emmy, Golden Globe and Screen Actors Guild Award, and the entire cast and crew were awarded the Women in Film Crystal + Lucy Awards for its “excellence and innovation.” Also it was probably the last time we’ll ever see Anne Heche direct any part of a lesbian film.
15. Lost & Delirious (2001)
Starring: Piper Perabo, Jessica Paré, Mischa Barton Director: Léa Pool
Based on The Wives of Bath by Susan Swan, the boarding school love story introduced us to three actresses we are not only familiar with but undying fans of now. It begins quite happily as a picture of young love but ends in a stunning loss that no one saw coming. It might have won some extra points for utilizing slow sad songs by Ani Difranco and Meshell Ndegeocello.
16. Show Me Love/Fucking Åmål (1998)
Starring: Rebecka Liljeberg, Alexandra Dahlström Director: Lukas Moodysson
In this Swedish coming-of-age story, a young lesbian with no friends and depressing life in a rundown town has a crush on a beautiful popular girl at her school. What starts as unrequited love ends in their being outed as a couple, but a vague yet positive conclusion kept us happily believing Elin and Agnes could make it through anything. A teen movie that is without cheesiness or cliched coming out moments, Show Me Love was lauded as a must-see film by straight and gay film festivals alike, including the British Film Institute, the Berlin Film Festival and GLAAD Awards.
17. The World Unseen (2007)
Starring: Lisa Rey, Sheetal Sheth, Parvin Dabas Director: Shamim Sarif
Adapted from her own novel of the same name, Shamim Sarif wrote and directed this historical romance about two Indian South African who fall in love during Apartheid. Lisa Rey and Sheetal Sheth also starred in Sarif’s I Can’t Think Straight, which came in at #2 on our list.
18. When Night is Falling (1995)
Starring: Pascale Bussières, Rachael Crawford Director: Patricia Rozema
Camille Baker, a literature professor at a religious college, falls in love with a female circus performer named Petra. The film was originally given a NC-17 rating, but was released on DVD with no MPAA rating at all.
19. Jamie and Jessie Are Not Together (2011)
Starring: Jacqui Jackson, Jessica London-Shields, Fawzia Mirza Director: Wendy Jo Carlton
A musical comedy that focuses on two queer best friends who are not together, though one of them is desperately in love with the other. The film features music from iconic lesbian musicians Tegan and Sara and God-des and She.
20. Gia (1998)
Starring: Angelina Jolie, Faye Dunaway, Elizabeth Mitchell Director: Michael Cristofer
Gia is an HBO-produced biopic about bisexual model Gia Marie Carangi whose meteoric rise through the New York fashion industry is cut short by her drug addiction. Not even her passionate affair with makeup artist Linda can get her back on track, and although she eventually is successful in her attempts to kick her habit, she discovers at the age of 26 that she has contracted AIDS.