Books about male characters who are a total mess?

Hey! I recently finished the television show Fleabag, which was an absolutely wonderful work of art. For those who haven’t seen, it’s about a well-intentioned woman who ultimately engages in a ton of self-destructive behaviors; she’s full of love, but an absolute mess.

I’m looking for a book with a similar character, but a man; I think it would be interesting to see a character like this on the other side of the gender divide.