Caleb’s review published on Letterboxd:
I'm just not wired for cringe comedy. Never been my thing. It's much easier for me to watch a disembowelment than witness someone deliberately embarrass themselves on a screen.
But I also couldn't get past the aspect of this project where Bo's character draws self-deprecating attention to his self-defeating self-awareness every 3 seconds, only to flippantly dismiss the notion of anything deeper than surface-level self-reflection. That's the punchline, I know. It's the punchline like fifty times, thanks to the constantly repeating lyrics. It's also not half as fresh or thoughtful as he seems to think (not to mention it's a hell of a lot of "self-").
Besides that we've got a lot of wedding standup from the mid-to-late aughts, pumpkin spice lattes and sexting jokes and the like. Teaching parents to use AOL/Skype/FaceTime. Plus the obligatory "white women on instagram, am I right, guys?" gags which have felt ubiquitous since the early 2010s and the rise of listicles. It's all been done to death and probably didn't need to be done again.
As to why the non-comedic mental health diary portions of this project largely don't land, plenty of folks have already said it much better than I could. You can find lots of reviews here articulating why white millionaire celebrities crying for the camera about the most insulated version of 2020 trauma imaginable—while also repeatedly emphasizing how hard it was to watch virtually everyone else in the world have a much worse time of it—might just be a tone deaf thing to put out into the world as a Netflix special.
Yes, Bo, lockdown sucked. I too was really depressed this year and aware of the extraordinarily privileged position from which I experienced that depression. That part's not deep. If you want to talk about the hurt you could just talk about it without all the irony-laden performative handwringing (and worse, handwaving) about other people's suffering and the nature of cracking jokes while the world burns. News flash: the world has always been burning in the sense you seem to mean here, of wide-scale and systemic suffering occurring outside—and sometimes within—your direct field of vision.
Or, at least, if you're going to raise issues like mass death and systemic racism and police brutality, you could treat them with more depth than as recurring punchlines about your own remove from them.
Should go without saying I hope real-life Bo is getting the help he needs and finding a way back to a better place than he was when he wrote this. Depression sucks whether or not you're a person with the resources to seek treatment. One of the things that sucks about depression is how difficult it can make it to separate the mental state we're in at a given moment from the reality of the world around us. Whoever greenlit this project for Netflix maybe should have helped identify that.