#42 -- "Our Gang" by Philip Roth
Here's an example of a novel that I'm reading a couple decades late (and actually, "Portnoy's Complaint" probably falls into the same category). In its time, "Our Gang" was pretty obviously groundbreaking satire, but now, after a couple decades of the Onion, it loses some punch. It's hilarious (a send-up of Richard Nixon) and had a bunch of spots that made me laugh out loud, but seems kind of light. As far as Roth's comic novels go, I'd recommend "The Great American Novel" over this.