I’m re-posting (sometimes in expanded form) a series of reviews of lesbian-themed movies that I originally drew up in answer to a request for recommendations of "good movies involving lesbian romances that don't end up with the protagonists deeply unhappy, dead, or both." To this set of criteria I’ve added the question, “Is the story primarily about coming out?” This set of index questions will necessarily involve some spoilers, but since I'm not reviewing any current releases, I think the statute of limitations has expired.
Many of these items are not currently in print. I'll link each to their imdb.com entry for reference. But for those currently available, Wolfe Video is the go-to distributor for lgbt movies.
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If These Walls Could Talk (2000) A television ... concept, I guess you'd call it, rather than trying to shoehorn it into "series" or "movie" or some such. Each set of shows revolves around the conceit of three different sets of inhabitants of the same location, at three different eras, each dealing with the same social "issue". The topic for the second "set" is lesbians, with stories set in 1961 (depressing and infuriating, no happy ending), 1972 (feminism vs. the Lavender Menace! butch-femme culture vs. crunchy-granola! happy ending!), and 2000 (in the heart of the "gay-by boom", light comedy, happy ending). Refreshingly, none of the stories is a basic "coming out" tale. While the first episode is Not Happy, it's the sort to drive you to march in the streets rather than to mope in the corner, and there isn't the slightest whiff of "punishment for sin" themes. Nobody turns straight or dies (well, technically someone dies but it's before the story opens). The middle episode is very atmospheric for its setting. Sure, it relies on "types" that veer close to being stereotypes, but they are also types that reflect actual significant themes and issues of the day. And the final segment, while still counting as a "period piece" at this point, is a cute snapshot of significant (though not universal) themes of the day. Given that the least positive segment comes first, watching the set as a whole helps wash the bitter taste away.
I don't know how well this triptych stands as "entertainment", but if someone is looking for an emotional understanding of what it meant to be a lesbian in recent generations, this is a useful contribution -- far more so than glamorized shows like The L Word.