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2. Boys Don’t Cry (1999)

Was 1999 the landmark year, the watershed year, for LGBT movies? I did not intend to but was genuinely surprised to find three movies from that year on my list. Of the three, however, it is the heartbreaking Boys Don’t Cry that deserves the number two spot today.

Hilary Swank plays Brandon Teena, a transgendered man who lives in Nebraska and faces constant persecution and threats because of his sexual identity. It is actually difficult to write a lot about this movie - recalling its well-acted, disturbing scenes is genuinely upsetting. Swank gives one of the best performances by an actor, in my view, of all time, and won a highly deserved Best Actress Oscar for it. Chloe Sevigny also dazzles as her love interest, who does not know that Brandon was born a woman.

It is predictable (and, I agree with some LGBT critics, annoying) that the lead character in this movie is another tragic figure whose existence ends in tragedy. But, it is also reality, as the story is based on a real person. Also, while the movie was being shot, and a year before it was released, the murder of Matthew Shepard in Wyoming shocked the nation. And, unfortunately, violence against transgender individuals continues to this very day, accounting for a ridiculously high number of violent hate crimes across the country, according to FBI statistics.

Boys Don’t Cry, then, was on the vanguard of exploring this issue. Where The Crying Game had been crude, and where Transamerica proved later to be emotional, Boys Don’t Cry was simply sincere, realistic, and tragic.

And, by opening our eyes to the issue and problem, it undoubtedly helped humanize LGBT individuals, and contributed to the cultural shift on LGBT individuals that led to Friday’s decision.

1. My Own Private Idaho (1991)

It’s an oxymoron, at times, to make these lists, because to say that this or that movie is better than another is so subjective as to be essentially pointless.

But, when it comes to LGBT movies, one can safely write outside the shadow of the beast that is taste-based classification. My Own Private Idaho is millennia ahead of the movies that followed it. Perhaps if Brokeback were eligible (after my arbitrary disqualification of it), it would give the Keanu Reeves/River Phoenix soft-core masterpiece a run for its money.

From Southern States to Idaho, the two star-crossed lovers discover the pain and beauty in a drug-fueled, stress-filled, loving and longing existence. Try as you may to enjoy the beautiful embrace of a long desired love, life simply gets in the way.

The out director Gus Van Sant (Good Will Hunting, Milk) weaves a tortured tale of tortured love with an ending as devastating as it is predictable (upped and destroyed further only by the reality of the tragic ending of River Phoenix himself in real life, not a long time later). But what makes this a spectacle of a movie, despite its standalone quality, is that it really pushes the envelope in treading into a specific niche of gay subculture. Gay marriage was won mostly based on the notion that gay men and women are just like your next door neighbors - the same, unthreatening. My Own Private Idaho reminds us of another facet - drugs, intense sex, and prohibited love. How ironic, and amazing, that in doing so, it opened the eyes of so many to the realities of a few…

As a parting thought: I hope to one day to be able to add to this illustrious list a movie about the stunning and dignifying battle for marriage equality that was achieved this week.

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