What's in a title? Perhaps the whole story, or nothing at all. The following books all start with Down And Out In... and diverge wildly from there. Most are humorous, though the style of humor varies. Whether it's the Paris slums or The Happiest Place On Earth, there's something to discontent everyone.
Down and Out in Paris and London is the granddaddy of them all, and the book that got George Orwell noticed. Autobiographical in nature, it tells of the very poor in both cities between the World Wars, even after the main character gets a job washing dishes in a luxurious Parisian hotel. Orwell's sardonic humor and view of society is on full display here, a precursor to his later works.
Down and Out in the Magic Kingdom has Cory Doctorow heading in the opposite financial direction, though his eye is definitely on Orwell. In a world without death, government, or money, what does one do? One can live at Disney World with a girlfriend a quarter of one's age and have a bromance with a guy who actually wants to go off into that good night in this delightful satire.
Kathryn Leigh Scott's Down and Out in Beverly Heels is a romp behind the scenes of Hollywood with someone who knows. Meg Barnes' husband scammed a bunch of people and disappeared just as Meg's acting career was starting to peter out and took her money with him. Back for pilot season, a determined Meg is told her husband may be alive and in California; hilarity (and romance) ensues.
Graciela "Ace" Jones is back from misadventures in Florida in Down and Out in Bugtussle and wants her job as art teacher back. Stephanie McAfee spins another down home yarn about the eccentric residents of this small, southern town and the outsize Ace.
A good introduction to the influential Tim Powers might be Down and Out in Purgatory, a collection of his short stories. A dark blend of genres, these tales are mostly set in California, but not the one in the tourist brochures. Atmospheric, compelling, and acclaimed, this may appeal to fans of Jim Butcher and China Mieville.
Have other places to be Down And Out? Tell us in the comments.