1. Under the Volcano
by Malcolm Lowry
An absolute masterpiece of spiraling inebriation unto death, written by the drunkest of drunks. Utilizing dramatic flashbacks and bursting with mystical symbolism, this novel charts the final, mescal-addled day in the life of fallen British Consul Geoffery Firmin. Under the Volcano plumbs the psychological depths of a willfully sought alcoholic hell. It is a testament to Lowry's vision that we eventually come to understand, even sympathize with, the protagonist's glorious failure. Neither justification nor condemnation, this haunting, beautiful book is a landmark of alcoholic fiction (and beyond that, one of the greatest epic novels, ever.)
2. Leaving Las Vegas
by John O'Brien
The movie is great; the book is even better. The prose is corkscrewed and wildly colorful in its depiction of the doomed affair of liquored-up Ben and whoring Sera--two decent souls who have simply given up on life. For sheer poetic renderings of the alcoholic mind, few contemporary writers have matched O'Brien's powerful, debauched style. Too bad he's gone. He shot himself dead in 1994.
by Charles Willeford
The pulpier side of dipsomania. It's a relentless narrative of skid-row despair and self-destructive love, buoyed by an endless flow of cheap whiskey. An utterly compelling and irredemptive read--like watching a train wreck, hungover.
by Charles Bukowski
This barely functioning alcoholic cornered the market on barfly bravado, and Factotum is perhaps the clearest, or bleariest, expression of Bukowski's unique genius. A dizzying travelogue of shitty jobs gained and lost on a tidal wave of rotgut hootch, it's funny, sad, vulgar, and infinitely readable. Love it or hate it, Bukowski's intoxicated oeuvre is America's most durable contribution to the international literature of delirium tremors.
5. Alcoholics Anonymous, a.k.a. the Big Book,
written by and for drunks
Lastly, for a compendium of boozy bad luck, you really can't beat this encyclopedia of crapulous behavior. It's the definitive bible of bottoming out. Each chapter gives testimony to the devilish allure of drink and its uncanny ability to sneak up and bite you in the ass. The accounts are bold, scary, and without self-pity. It ain't exactly high lit, but it's real.