These days there is an entire market of LGBT entertainment, even a distribution label focusing exclusively on films with these characters and themes, but it is still rare for a movie with gay and lesbian themes at the forefront of the narrative to become mainstream successes. What is really remarkable is that Kissing Jessica Stein still seems ahead of its time twelve years after it was made. How many widely distributed LGBT romantic comedies have been released since this film?
In many ways Kissing Jessica Stein just feels like a Woody Allen film with a female perspective and a lesbian twist. Jennifer Westfeldt stars as the title character, a neurotic Allen stand-in with an inability to find the right guy while working as a journalist in Manhattan. When Jessica reads a romance ad from a woman with similar tastes, she tentatively enters in a relationship with Helen (Heather Juergensen). The film is not dedicated to any particular plot development, leaving much of the film’s entertainment up to the variety of vignettes about Jessica’s transition into lesbianism.
Although there are some structures in the film which have clearly been lifted from the romantic comedy handbook, this is clearly an independent film. It has the dialogue-heavy meandering that most studios would quickly replace with melodrama. Instead we have nothing but the performances and dialogue to carry Kissing Jessica Stein. The performances by the two leads are effortless, which probably comes from the fact that the pair also wrote the screenplay.
The Blu-ray release includes two audio commentaries; one by Charles Herman-Wurmfeld and cinematographer Lawrence Sher, and another with stars and co-writers Juergensen and Westfeldt. The deleted scenes includes in the special features also have optional commentaries. The extras also include outtakes and an alternate ending, as well as a behind-the-scenes featurette.
Entertainment Value: 7/10
Quality of Filmmaking: 7.5/10
Historical Significance: 6.5/10