It's been quite a while since I read The Crying of Lot 49 but I don't remember enjoying it that much. The only previous Pynchon book I read with enjoyment was Vineland and that's considered one of his worst. Gravity's Rainbow was over my head and Mason and Dixon wore me down (even though it contained some very good bits).
Take this with a grain of salt (I heard it from a guy I only know on the internet, and he said to take it with a grain of salt himself - like, his nephew played on a softball team with Pynchon's son, one of those kinds of stories) but anyway according to him
Vineland is Pynchon's favorite of his own novels.
Also, a
Naked Lunch aside -- I still have the copy I read at age 19, and my wife had to read it for grad school. But then she noticed that like 30 pages were missing from the last third. So I said, oh no, it's not going to make any sense now! I crack myself up.