Fifty years ago, Roy Orbison’s “Oh, Pretty Woman” skyrocketed to Billboard’s Number One spot. Written (along with Bill Dees) in tribute to Orbison’s first wife, Claudette, the iconic track was a departure from his usual themes of heartbreak. Nevertheless, fans loved it, and it topped Billboard for three weeks and reached Number One in 22 countries simultaneously, in the end standing as the most celebrated single of Orbison’s career.  Its popularity grew even more once it inspired the title of and was featured in the much-loved 1990 film Pretty Woman. The following year, Orbison received a posthumous Grammy for the live version of “Oh, Pretty Woman” featured in his 1987 “A Black and White Night” concert, which was aired as an HBO special January of 1988. The distinguished backing band included Elvis Costello, Tom Waits, kd lang, T Bone Burnett, Bruce Springsteen and Jackson Browne (an honoree at next Wednesday’s AMA Awards), but even then it was Orbison’s stage presence that swayed the focus back onto him, defining the classic that still sounds fresh and original 50 years later.

Check out some of Orbison’s “A Black and White Night” performance below.

– Samantha M. Lopez