Heartbreak Hotel • 1956

The single that made Elvis Presley a star had the saddest possible inspiration. The exact source for the “lonely street” walked by the singer in the lyrics (by Tommy Durden) has been attributed to a variety of events in newspaper stories over the years—including a suicide and a criminal who lost his life during a robbery. At the time, 21-year-old Elvis had just been signed to RCA Records and was an unproven seller, so the company’s executives initially questioned if such a morbid song would connect with his potential teen audience. But the tune’s palatable ache made fans swoon. “The way Elvis sang it captured a rebellious loneliness,” Schilling says. “It hit in the same way that James Dean and early Brando did at that time.” It topped both the country and pop charts.