reprobate

These days, calling someone a "reprobate" is hardly a condemnation to hellfire and brimstone, but the original reprobates of the 16th century were hardened sinners who had fallen from God's grace. By the 19th century, "reprobate" had acquired the milder, but still utterly condemnatory, sense of "a depraved person." Gradually, though, the criticism implied by "reprobate" became touched with tolerance and even a bit of humor. It is now most likely to be used as it was in this August 1995 New Yorker magazine article about the death of musician Jerry Garcia: "It was suddenly obvious that Garcia had become, against all odds, an American icon: by Thursday morning, the avuncular old reprobate had smuggled his way onto the front pages of newspapers around the world."