Just watched the winning Tropfest film, "Bamboozled". Weird. I mean, I know gag films always dominate at Tropfest. That's partly a function of the voting structure, where a winning film has to appeal to all of the panellists. Short films can't reliably tell an intricate story, there isn't time. What they can do is either be experimental in structure, or offer a gag. And the thing about experimental films is that they polarise - some will love them, some will hate them. But the gag films reliably "work". They don't feel too short, they don't feel too weird - they achieve a modest objective, successfully. So the fact that a film with this particular structure won is no surprise.
What's weird for me is that the gag is (for my money) poorly executed. They over-labour the punchline, which drags on for almost 2 minutes, while they explain that there's a reality tv show, that he's on it, that his girlfriend was involved etc. The first 3 seconds after the big reveal are more than enough to let the audience nut out the gist of the punchline - more than that and the filmmaker becomes a drunk uncle at a wedding, constantly repeating a bad joke because he thinks you didn't get it. If they wanted a sharper punchline, they needed to find a way to plant the existence of the "Bamboozled" show, or at least the idea of reality TV more generally, or the suggestion he mistreated his ex, or something, so that the big reveal could be shorter, sharper, and punchier. It's also an ugly shift in tone and aesthetic, after an elegant montage we go to choppy handheld.
It also doesn't feel like the prestige corresponds with the pledge and turn - we build up a story about acceptance and connection, about possible fluidity of sexuality and gender identity, and so forth, and then the twist is that he was lied to. But the lie wasn't by that point the foundation of their connection, the connection was confusing and confronting to the protagonist, but it wasn't very elegantly turned on its head in the denouement.
It was rather like the "Knock Knock" jokes children tell before they've mastered the format.
"Knock knock."
"Who's there?"
"Phillip."
"Phillip who?"
"Dog farts!!"
The other tricksy thing is the play of sympathies. We get drawn in by the bewildered, hesitant acceptance of the protagonist in the first part. He wins us over by being open-minded but not gullible, and by having an ex who seems to remember him fondly. No fatal flaw is established - we learn very little about him which is negative until *after* the big reveal, and too late for us to have time to reorient our sympathies. The regret after the night before is a dick move, but ultimately his prerogative (anyone's allowed to regret sex) and he's building up to a way to gently step back when the *big loud noises* trigger his fight-or-flight response and leave him acting poorly. But because the ending is so contrived and disconnected, it's all just very emotionally alienating.
Oh, and I should perhaps also mention it's likely to distress GLBTQAI and pretty much the rest of the alphabet. Others will grapple with those aspects better than I.