The Disappointments: Season 1 (Web Series)

Honestly kind of surprised this one flew under my radar for so long, I'm just now catching wind of it. This is a crowdfunded comedy drama following three gay best friends dealing with life, love, and letdowns as they hit their late fifties and early sixties. What do you actually do once it hits you that time's running out, that you've got more road behind you than ahead, and that your career, your relationship, where you're living, basically your whole life, didn't turn out anything like you pictured when you were younger? It runs eleven episodes, each clocking in around ten minutes. A re-edited Director's cut version was recently released this year with 5 episodes.

Ray, Gary, and James have been friends for what feels like forever, and now they're all in what should be their golden years. Ray's a screenwriter who's been struggling financially since work just isn't coming his way, though he's got a younger, attractive boyfriend who's a little awkward socially. Gary's a singer and actor who just found out he has anal cancer, and he's leaned heavily on drinking to cope, unable to bring himself to actually tell his friends what's going on. Then there's James, an actor who can't land any roles, furious at his agent, and carrying around a serious chip on his shoulder. Despite everything, these three lean on each other, constantly questioning how and where their lives went sideways, with no savings, no home ownership, no retirement fund, wondering how they're supposed to actually survive at this stage. Things shift when Ray's ex, someone who's also been a longtime friend to the group, dies by suicide, and that moment also exposes just how surface level a lot of friendships within the gay community can be, since nobody stepped up to help this guy while he was struggling. Later in the season, Dwight ends up moving in with Ray while his own place is getting renovated, which works out since it helps Ray with bills and gives them time together. Across the rest of the episodes we follow these three friends alongside Dwight's storyline too. The show wraps up a year later, revealing that Dwight and Ray are no longer together, though we're never told why. Maybe that gets explained in a second season.

At its core, this is about three gay men who've spent decades trying to break into the LA entertainment scene with only limited success. Even after all this time, they're still barely scraping by, teetering on the edge of homelessness. It's a genuinely serious topic, but the show handles it with a light, comedic touch while still making you think hard about what happens in old age if you never really planned ahead. Not many shows even touch on this kind of subject matter. The acting across the board was solid, though the writing occasionally felt a bit surface level. A little more depth given to the characters would've gone a long way. That said, it's pretty clear this was made on a tight budget, so given what they had to work with, they did a good job. The dynamic between Ray and Dwight felt genuinely believable and sweet to watch. The way he casually settles into Ray's life and then dishes out solid, practical advice about living within your means is honestly kind of touching. This show keeps things simple, grounded, and easy to watch. Genuinely looking forward to seeing where a second season takes this. (5.5/10)