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Scudder debuted in 1976's The Sins of the Fathers as an alcoholic ex-cop who had recently quit the NYPD and left his family after accidentally causing the death of a young girl. Living in a rent-controlled hotel room in Hell's Kitchen, he earns his living as an unlicensed private investigator - or, as he puts it, "doing favors for friends." The series' overarching theme is mortality: the early entries are filled with scenes of Scudder alone in churches, compulsively tithing his small income, lighting candles for whatever deceased figures happen to be on his mind - and always for the girl whose life he had inadvertently taken.
The fifth entry, 1982's Eight Million Ways to Die (often cited as the best), is the first to notably move the character forward, concluding with Scudder introducing himself at an Alcoholics Anonymous meeting. Block planned to end the series there, but a promise he'd made to supply an editor friend with an original short resulted in "By the Dawn's Early Light," a story set during Scudder's drinking days but told from the perspective of a recoverer. Block would go on to expand on that with 1986's When the Sacred Ginmill Closes, which not only resurrected the series, but proved a favorite of both the author and his fans.
From then on, Scudder's circumstances rarely remain the same for long: 1990's A Ticket to the Boneyard reunites him with Elaine Mardell, a hooker from his days on the force, and concludes with him staging the suicide of a man who had threatened their lives - a decision he recalls in a number of subsequent volumes. 1991's A Dance at the Slaughterhouse introduces TJ, a young Times Square hustler who becomes Scudder's protégé and closest ally. 1992's A Walk Among the Tombstones sees him struggling with Elaine's role as a prostitute (as well as a pair of violent kidnappers), while 1994's A Long Line of Dead Men ends with the two marrying.
Though Scudder never takes another drink (coming closest in Boneyard), alcohol continues to play a large role in his life: he continues to attend Alcoholics Anonymous meetings (which constitute a central setting of the later novels), and his best friend, Mick Ballou, is a career criminal and saloonkeeper with whom he often spends long nights. He also has a standing Sunday night dinner with his sponsor, Jim Faber, who eventually becomes a surrogate father figure.
Scudder has relaxed somewhat in recent entries, and is now far more apt to enjoy an evening at Lincoln Center with Elaine than he is to take on a job. 2005's All the Flowers Are Dying, the sixteenth title in the series, seemed to have been written as a possible final chapter, but a new Scudder book, titled A Drop of the Hard Stuff, -- a second "flashback" novel -- was published in 2011.