Al Jolson

At the dawn of the 20th Century, Al Jolson ushered in the age of the media superstar. He ruled stage, records, and screen with the first crossover talking picture, The Jazz Singer, but his over-the-top style went out of fashion following the commercial ascent of Louis Armstrong and Bing Crosby. He earned a new audience by tirelessly entertaining the troops during WWII, and by his old LPs being name-dropped as the collector's ne plus ultra on Seinfeld.