Pap Finn - The Adventures of Huckleberry Finn by Mark Twain
Regularly beats the stuffing out of one of the Western canon's most beloved protagonists. Ghostlike, disheveled and typically "drunk as a fiddler," he even tries to steal Huck's reward money, which the poor kid spent the entire last third of The Adventures of Tom Sawyer earning.
Abe North - Tender Is the Night by F. Scott Fitzgerald
Failed musician with a propensity for getting his friends caught up in dangerous trouble. Abe gets robbed at gunpoint while drunk, accuses the wrong man of the crime, and ends up bludgeoned to death in a speakeasy.
Sebastian Flyte - Brideshead Revisited by Evelyn Waugh
Literature's most famous lapsed Catholic. Flyte drinks either out of guilt over abandoning the church, or repressed homosexuality, or some combination of the two. None of this is presumably helped by the constant presence of his handsome, agnostic school chum Charles, who narrates and eventually falls for Sebastian's sister. After Sebastian gets kicked out of the university, everyone gives up on him, with the lone exception of his darling stuffed teddy bear, Aloysius.
Julian English - Appointment in Samarra by John O'Hara
Depressive, womanizing Cadillac dealer who self-destructively, and somewhat inexplicably, stumbles toward his inevitable rendezvous with death. The protagonist is almost as unlikable as John O'Hara himself, a man who spent his entire career alienating other writers and demanding a Nobel Prize. Julian commits suicide via carbon monoxide in the end, while O'Hara, despite the lack of a Nobel, passed away of natural causes, inscribing for himself the modest epitaph "Better than anyone else, he told the truth about his time."
Michael Henchard - The Mayor of Casterbridge by Thomas Hardy
"Hay-trusser" who becomes so soused he sells his wife and daughter at a country fair for five guineas. Penitent, he swears off alcohol for good and goes on to become a successful merchant and mayor of Casterbridge. Then his wife and daughter show up and ruin everything. His final wish is to be forever forgotten.
Adapted from Scatterbrained (HarperCollins), which is available at leading bookstores. For a daily dose of quirky fun, visit MentalFloss.com and check out mental_floss magazine at your local newsstand.