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Roy Orbison
Charted: #1 in September 1964
Oh, Pretty Woman" held the #1 position for three weeks in the summer of 1964 and was the high watermark in Roy Orbison's career. With a simple, straightforward arrangement, it was markedly different from Orbison's previous hits. What it lacked in orchestration was compensated by a driving rock-and-roll rhythm, and where Orbison's voice would previously ascend to angelic heights, it now descended into a lustful growl. The song has him idly watching a pretty woman as she walks past him, while he imagines being able to seduce her. The growl became a trademark of sorts and helped Orbison seem less pathetic than his previous material had painted him to be. He even gives the song an upbeat ending, when the mysterious woman turns around and walks back toward him.
After "Oh, Pretty Woman," Orbison was destined for some drastic and devastating changes. He changed labels, from the small, independent Monument to the corporate monolith of MGM. He, along with just about everybody, was overrun by the British Invasion, and his records became less and less popular. His last entry on the Top 40 was in May 1966, with an incongruous song called "Twinkle Toes." In June 1966, tragedy began to take away what remained of his life when his wife was killed in a motorcycle accident. Then, two years later, two of his three children died when his house caught fire.
After an understandable period of mourning and confusion, Orbison returned to music with his credibility and talent firmly intact. Before his untimely death by a massive heart attack on December 6, 1988, he became a member of the mega-superstar group The Traveling Wilburys and was subsequently inducted into the Rock and Roll Hall of Fame.
 
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