Bing Crosby

Harry Lillis Crosby Jr. came up in 1926 as recording technology shifted, and he bent the new microphones to his advantage: a low, close style that made every listener feel like the only one in the room. By World War II, Yank magazine called him the single biggest morale boost for overseas servicemen, and in 1948 American polls named him the most admired man alive, ahead of Jackie Robinson and the Pope. He won an Oscar for Going My Way in 1944, ruled the box office for five straight years, and in 1946 alone starred in three of the year's five highest-grossing films. Between pictures he recorded over 1,600 songs, bankrolled the magnetic tape revolution at Ampex with $50,000, and convinced ABC to let him prerecord his radio shows - a practice that became industry standard. He also bought TV stations, bred racehorses, and co-owned the Pittsburgh Pirates through two World Series wins. He died in 1977, three decades after "White Christmas" made him the sound of every holiday since.