He sang with the soul of an old sage, but Otis Redding didn’t live to see his 27th birthday. Less than two weeks before Christmas in 1967, Redding was killed in a plane crash in rural Wisconsin, along with his manager, three bandmates and the plane’s pilot. Just months before the fatal crash, Redding introduced songs like “Try a Little Tenderness” and “These Arms of Mine” to an entirely new fan base at the Monterey Pop Festival, a California concert that would inspire Woodstock two years later. But it was the posthumously released “(Sittin’ On) The Dock of the Bay,” a bittersweet ballad recorded just three days before his death, that became Redding’s first and only No. 1 single. In the three years following his death, his record company released three albums — The Immortal Otis Redding, Love Man, and Tell the Truth — all of which produced a spate of hits, including “Hard to Handle” and “I’ve Got Dreams to Remember.” In 1989 he was inducted into the Rock and Roll Hall of Fame.