“The Disappointments” Season 2 Is Streaming Free On YouTube Right Now!
The Humanitas Prize-winning web series about three mates over 50 figuring out love, work and everything in between is back with new episodes.
What to know about The Disappointments
The Disappointments follows longtime friends Ray, Gary and James as they face career setbacks, romantic complications and the challenge of redefining their lives in middle age. Created, written and co-directed by Rich Burns, the series was entirely crowdfunded and made on a shoestring budget. It first premiered in late 2021, and the first season went on to become the first web series ever to receive a Humanitas Prize, an award that honours writers whose work thoughtfully explores the human condition.
Season 2 picks up where the cliffhanger left off
Season one ended with a time jump that revealed Ray and Dwight had broken up with no explanation. In season two, each of the three friends finds himself with new career prospects. Ray lands a job writing on a girls’ animated series and struggles to fit in with a room full of Gen-Z writers. Gary gets hired as the co-host of a talk show and starts preparing to film the pilot, while an unexpected new relationship develops. James, now a newly licensed real estate agent, finds a mentor at a prestigious Beverly Hills firm, only for things to get complicated when the pair start a sexual relationship.
The cast
Burns stars as Ray Russo, Gedde Watanabe plays Gary Chen, James Campbell is James Caldwell and Trevor LaPaglia returns as Dwight. Watanabe is best known for his role as Long Duk Dong in the 1984 John Hughes film Sixteen Candles.
Why this show matters
Representation for men over 50 on screen remains rare. Burns has spoken openly about that gap. “For me, I don’t see a lot of representation of guys in their 60s trying to fix their disappointing lives,” he told Out magazine. The show is funny, grounded and drawn from real life. It doesn’t sanitise its characters or their situations. Burns has also mentioned the possibility of a feature film, noting that a third season would need to be fully viewer-funded.
Where and when to watch
New episodes drop every Sunday on YouTube at 1 pm ET / 10 am PT, running through 10 May 2026. The Director’s Cut of season one is also available on the same channel. Both seasons are free to watch.
