The record in context

The most famous guitar riff of Roy Orbison’s career was written in about forty minutes, on a summer day in 1964, because his wife walked into the room. Orbison and Bill Dees were writing at Orbison’s house when Claudette came in to say she was going out. Orbison asked if she needed any money; Dees shot back, “A pretty woman never needs any money.” Forty minutes later, “Oh, Pretty Woman” was finished — one of the fastest-written, biggest-selling singles in pop history.

The recording session was Orbison’s most deliberate attempt yet to make a record that rocked. He booked Nashville’s finest — guitarists Billy Sanford and Jerry Kennedy among them — and, unsatisfied with a single drummer’s attack, brought in a second drummer so the beat would hit twice as hard. The details are pure Orbison eccentricity: the playful growl in the vocal was borrowed from a Bob Hope movie; the famous cry of “mercy!” came, by his own admission, at a moment when he could not quite hit the note he wanted — so he turned the miss into a hook.

Released in August 1964, the single did what had seemed impossible: it broke the British stranglehold on the American charts. It spent three weeks at number one in the US, topped the charts in Britain as well — the second of Orbison’s two UK number ones in that remarkable 68-week run — stayed on the American charts for fourteen weeks, and sold more than seven million copies worldwide. It entered the Grammy Hall of Fame, and a quarter-century later the film Pretty Woman would carry it to a whole new generation. It remains, by any measure, the biggest record Roy Orbison ever made.

Listen closely

Listen to the riff. Those opening guitar notes — dum-dum-dum-dum-dee-doo-wah — are among the most recognizable in pop, and they never let up. The song is built like a coiled spring: the riff repeats, the tension builds, and Orbison’s vocal rides above it with a leering, almost comic confidence that his ballads never allowed. This is Orbison having fun, and the fun is infectious.

Listen for the “mercy!” It arrives exactly where a lesser singer would have smoothed over a rough note, and it is the most human moment in the record — a yelp of desire that is also, if you listen closely, a yelp of effort. Pop history is full of accidents that became signatures; this is one of the greatest. And listen for the growl underneath the verses, that Bob Hope-inspired playfulness: the Big O, the high priest of heartbreak, doing comedy.

Then listen to the drums. Two drummers, pounding in unison, give the record a physical weight that none of Orbison’s earlier hits had. This was a man who had spent four years proving that space and strings could top the charts; now he proved he could do it with sheer force. The Beatles’ grip on 1964 was broken, in the end, not by another beat group but by a Texan in sunglasses with a forty-minute riff.

And listen to the story the song tells. For all its swagger, “Oh, Pretty Woman” is a fantasy — the singer watches the woman walk by, imagines her turning back, and the whole thing may be happening only in his head. Even at his most playful, Orbison couldn’t quite leave loneliness behind. The final “come with me, baby” is triumphant, but listen to how much wanting is underneath the triumph. That undercurrent is what separates a novelty from a classic.

Listen to the afterlife. “Oh, Pretty Woman” refused to fade: Van Halen took it back into the American Top 20 in 1982 with a faithful, guitar-heavy cover, and in 1990 the film Pretty Woman — named for the song, built around it — carried it to a generation born after its release. Few records have been revived so often without ever sounding dated, and the reason is in the grooves: the riff is elemental, the vocal is joyful, and the whole thing runs on an energy that doesn’t belong to any era. It is the rare oldie that still sounds like it could be a hit tomorrow. Pretty woman, indeed — the song, like its subject, never seems to age.