The Day of the Locust by Nathanael West
Think criticism of Los Angeles as a soulless husk of a place is a product of the excessive '80s or the corporate oughts? The bitterness goes way back. West's 1939 book starts with disillusionment and ends in a riot.
All the characters are broken people, somehow loathsome and sympathetic at once, and while all aspire to life in The Pictures, their Hollywood is one of chipped glamor masking delusion and rage.
Though it's a raw story, and bad stuff happens to nearly everybody, much of the prose is just gorgeous. The descriptions of Homer Simpson's (not that one) hands, for starters.
Macabre fact of the day: West died in a car crash while speeding to attend F. Scott Fitzgerald's funeral.