I tend to steer clear of specials by famous observational comics. At a certain level of fame, I find, their observations just aren’t interesting anymore. Without naming names, I think you’ll agree there is a class of contemporary comedians who may or may not have deserved to become successful some years ago and now live on a different planet. Their problems are the problems of famous people, which don’t interest me, and when they try to talk about the real world, I can tell it’s basically a thought experiment to them. This is probably inevitable; at the very least, it's reliably observable. Comedians mine their subject matter from some combination of the self and the world, and success is apt to warp one’s perspective of both. The cruel bargain of the opinion-having business is that if you’re good at it, your reward is a set of material conditions that might just make you bad at it. Which is partly why I gravitate towards artists who operate in more performative modes, the ones less likely to bring personality-altering success and more likely to involve a subordination of the self, although naturally there are plenty of exceptions on all sides.
On the other hand, I think there is a narrow level of success that heightens rather than diminishes an observational comic’s powers, and it’s whatever level Todd Barry is in. He brags about his own celebrity status repeatedly throughout his new special, Domestic Shorthair, striking a deliciously smug tone that may only be possible when that status is, well, a joke. In comics who haven’t earned the right to brag, smugness about one’s reputation is just distracting: hang on, am I supposed to give a shit about this asshole? In comics who have earned the right to brag, smugness can be very disturbing: wow, so, six specials about trans people, huh? Somewhere in the middle lies the magic zone, the domain of the journeyman comic, where smugness becomes a self-deprecating joke we’re all in on: it is, in fact, pretty funny to pretend that having a bit part in Pootie Tang gives someone prestige.