I watched two seasons and the first episode of the third season, but I think I'm done with this show. It started off as interesting and funny but then got really uncomfortable and depressing early in the second season. The episode at the end of the season with Chris Rock (in which Louis ends up stranded in New Jersey) was especially painful.
I understand the appeal of the "awkward and embarrassing" style of humor in a philosophical sense, but it doesn't particularly appeal to me personally. For what it's worth, I wasn't a big fan of Curb Your Enthusiasm either. I mean, I got it, but I didn't enjoy it.
I am a major supporter of the "no hugging no learning" Seinfeld brand of humor, and yet I didn't like Seinfeld itself because I don't find irony to be automatically funny.
I guess, for me, humor has two components:
(1) It needs to be good-natured – although I think I might be using a special definition of "good-natured" here. Humor can be gross or angry or sarcastic or politically incorrect, but it needs to be coming from a good place. For example, mocking the weak from the vantage point of the strong is never going to be funny. Likewise, reinforcing stupid stereotypes is never going to be funny. Irony can be brilliant, but only if it overturns majority opinions instead of reinforcing them.
(2) It needs to be clever and original and unexpected. I don't like "wacky" humor because it follows set patterns, but I can get behind "over the top" humor because it challenges boundaries. I think this is one of the reasons why gallows humor works so well and always stays fresh – because death/disfigurement/disease is a fairly strong boundary, and most of us are always in a sustained state of individual negotiations with it.
So yes, rape jokes can be funny. Gay panic can be funny. Dead baby jokes are funny. Horror movies are especially funny. The ridiculous and hateful shit that people write on 4chan and Reddit and Something Awful is fucking hilarious (as long as you don't take it seriously or it doesn't actually become serious).
Louie works best when it focuses on Louis's two daughters and his struggles as a single dad. This is outside the show, of course, but my favorite Louis CK routine is
the Jizanthapus story. This is funny not just because kids are weird and do bizarre and random things that are funny in and of themselves, but also because we as a society don't really talk about the more terrible aspects of raising a child. It's absolutely not acceptable, for instance, to talk about removing liquid feces from your daughter's vagina, but this is a real thing that happens, and it's impossible to discuss without either creating a humorous situation or coming off as a total creeper. In other words, we need to talk about that sort of thing, and we need humor to talk about it. Louie does this type of "acceptable social outlet" humor really, really well – and not just with kids, but also with topics like the stigma surrounding discussions of race and sexuality.
Louie doesn't work when it's being self-indulgent. When it's about an adult white man with a modest amount of money and success not being given something he wants and then getting upset about it, it's just not funny. When it's about how relationships don't work because men are lazy and women end up overcompensating, I don't care. When it's about how men don't listen to women and engage in invasive and stalker-ish behavior, it's kind of a downer.
Anyway, people keep recommending Parks and Recreation. I tried to watch it from the beginning a year or two ago and didn't like it, but apparently one needs to start from the second season. I'm going to give it another shot this weekend. Wish me luck?