That was my last midnight release, and I did love that one, but it still had it's trademark humor sprinkled in so I didn't take it as serious.
Man, I replayed it recently and it's hard to find a lot of the story funny imo. It's just everything goes bad once Niko gets here. They bomb Romans business, kidnap him, you gotta choose between Playboy x and Dwayne, the two Irish brothers, that one Dominican chick gets paranoid and shoots that one nikka while he's shooting his show and goes to prison
And then the two endings leave somebody very important dead and people hating you.
It's one of the most nihilistic games because at the end of the day you realize you and the ones that survived (besides kate and kinda roman) are some of the worst people alive and your only satisfaction is the money you got that you can't even spend.