The Disappointments: Season 1 (Web Series)

Honestly, I’m kind of shocked this stayed off my radar for so long because I’m only just hearing about it now. This crowdfunded comedy drama follows three gay best friends navigating life, love, and disappointment as they enter their late fifties and early sixties. What are you supposed to do when you realize time is running out, there’s more road behind you than in front of you, and your career, relationship, home, and pretty much your entire life look nothing like what you imagined when you were young? There are eleven episodes, each running about ten minutes. A re-edited 5-episode Director’s cut version was also released recently this year.

Ray, Gary, and James have seemingly been friends forever, and they’ve now reached what should be their golden years. Ray is a financially struggling screenwriter because work simply isn’t coming his way, although he does have a younger, attractive boyfriend who’s a bit socially awkward. Gary, a singer and actor, has just learned that he has anal cancer. He’s been relying heavily on alcohol to deal with it and can’t bring himself to tell his friends what’s happening. James, meanwhile, is an actor who can’t get cast in anything, is enraged with his agent, and has a major chip on his shoulder. Through it all, the three depend on one another while repeatedly asking how and where their lives went wrong. With no savings, no homes of their own, and no retirement funds, they wonder how they’re possibly meant to survive at this point. Everything changes when Ray’s ex, who has also been a longtime friend of the group, dies by suicide. His death also reveals how surface level many friendships in the gay community can be, as no one came forward to help him while he was struggling. Later in the season, Dwight moves in with Ray while his own home is being renovated. The arrangement works out because it helps Ray cover his bills and lets them spend time together. The remaining episodes continue following the three friends, along with Dwight’s storyline. The show ends one year later with the revelation that Ray and Dwight are no longer together, but we’re never given a reason. Maybe a second season will explain it.

At heart, the show focuses on three gay men who have spent decades attempting to make it in the LA entertainment industry, with only limited success. After all these years, they’re still just scraping by and hovering dangerously close to homelessness. That’s genuinely heavy subject matter, yet the show approaches it with a light comedic touch while still pushing you to think seriously about what old age looks like when you never planned for it. Very few shows tackle anything like this. The acting was solid all around, although the writing sometimes came across as a little surface level. Giving the characters slightly more depth would’ve made a big difference. Still, the limited budget is pretty obvious, and they did a good job considering what they had available. Ray and Dwight’s dynamic felt truly believable, and it was sweet to watch. There’s something honestly kind of touching about how naturally Dwight slips into Ray’s life before offering him practical, sensible advice on living within his means. The show is simple, grounded, and an easy watch. I’m genuinely excited to see where they go with a second season. (5.5/10)

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