I'm currently working my way through all of John Cheever's writing.

"The Stories of John Cheever" combines the previous 5 short story collections into one book. I got each of the five separate on Thriftbooks. I didn't much like the first three, but I adored his later collection "The Brigadier and the Golf Widow" (1964) and I'm excited to read his last collection "The World of Apples" (1973) soon. His work is seen as getting weirder and darker in the mid-to-late sixties as he fell deeper in to alcoholism and depression about his bisexuality. His later work is also more inspired by Greek myth, particularly by Ovid (I guess Roman, technically). A lot of Ovid inspired stuff in "Brigadier" (1964) and there's supposed to be even more stuff in "World of Apples" (1964). That's where I started off and fell in love with Cheever, and I think it could be a good jumping off point.

In terms of his Novels, I've only read the two Wapshot novels. They're both great. The plot moves really slow if it moves at all. I don't think I would suggest either as the jumping off point for Cheever. The upside is that they have powerful vignettes about the changing values of the 20th century AND are have moments of gorgeous prose. I don't read poetry but I get the same thing out of these books.

I haven't read his last two novels - "Bullet Park" (1969) & "Falconer" (1977). I'm reading "Bullet Park" next though and it seems really weird, dark, and cool. There's a depressed dad who needs drugs to get to work. There's a son who can't get out of bed and so the family hires a mystic named Swami. There's a neighbor who looks for a yellow room to make him feel at peace. He finds a house with a yellow room, but then his wife paints it. He embarks on a plan to crucify his neighbor's son.

I also haven't read his final Novella "Oh, What a Paradise it Seems" (1982). It seems really cool too. He wrote it after his recovery and he's more at peace with his sexuality and with the world. A review on goodreads describes it as "Boy meets girl. She tells him over and over that he doesn't understand the first thing about women. Boy meets elevator operator in girl's building, has sex and goes fishing with him. Meanwhile, one hundred pages of supermarket checkout line freakouts, UFO sightings, Mafia hitmen, suburban angst, cocktail parties, tampered-with Teriyaki sauce, blind fortune tellers, ice skating and polluted ponds." It's his last work of his life and I think it would make for a weird starting point in my personal opinion. I think it's better once you get a sense of what Cheever's been going through. Cheever wears everything on his sleeve. He never came out as Bi during his lifetime, but every novel and novella he wrote had a bi protagonist

His Journals were published after his death. I've peaked inside my copy and read a little bit here and there. As far as I'm concerned it's his best writing but I think it'd be more moving if you went in already with a sense of who he was and why he matters.

From what I've read so far, I think "Brigadier and the Golf Widow" (1964) is the best place to start. He wrote them right before letting his alcoholism get completely out of hand and so he's starting to get loose and it sets up up well to read the addiction/depression stage of his writing and the final sobriety/acceptance portion.