With his close, sighing delivery, Bing Crosby set the template for romantic crooners for decades to come. The approachable singer and Hollywood star held breezy sway over audiences from the late 1920s well into the ‘50s, and his quivering yuletide chestnut “White Christmas” is still the best-selling single of all time. But beyond his jaunty vocal charisma on playful hits like “Swinging On a Star,” Crosby immortalized the broken dreams of the Great Depression with the haunting “Brother, Can You Spare a Dime?”—a remarkable adaptability that kept him fresh through rapidly changing eras.