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“It was an exceptionally long time to spend on one song” – the co-writer and guitarist on Roy Orbison's Oh, Pretty Woman tell the story of a classic song

Roy Orbison
(Image credit: David Redfern/Redferns)

The '60s was the decade that shot the humble guitar riff to the forefront of the songwriting pantheon, changing the face of modern music and duly launching a thousand guitar heroes in the process. From The Kinks’ You Really Got Me through Jimi’s Purple Haze onto Led Zep’s Whole Lotta Love, the riff was now king and here to stay for the long haul – and Roy Orbison’s Oh, Pretty Woman deserves to be judged up there with the best of them.

By the time the track was released in the late-summer of 1964, Orbison – with his characteristically cool Ray-Bans, black threads and dyed black hair – had become one of the most successful singers on the planet, and this riff-fuelled love song scored him yet another chart topper on both sides of the pond. 

But with the ‘British Invasion’ bands cockily waiting in the wings and on the verge of re-writing the rock ’n’ roll script forever, sadly Oh, Pretty Woman would be the last big hit that Roy Orbison ever had. The song was co-written by Orbison and Bill Dees, who had been working with Roy since 1962, and 1964 had already gifted the pair a UK No 1 and US Top 10 placing with It’s Over.

After that, we both chipped in and within an hour and a half – before she got back to the house – we had it written

Billy Dees

Dees told Total Guitar in 2011 about how their second smash hit was inspired by Roy’s first wife, Claudette: “[Roy and I] were sitting at their kitchen table and [Claudette] came bopping down the stairs. And she says, ‘Let me have some money’ and he says, ‘What do you need some money for?’ and she said, ‘I’m going to the store’. 

"Then they walked off about 15 or 20 foot and it was all kissy-kissy whispering and, when he came back to the table, I was standing up with a guitar and I sang, ‘Pretty woman…don’t need no money’ and then he sang, ‘Pretty woman… walking down the street’. After that, we both chipped in and within an hour and a half – before she got back to the house – we had it written.”

The following Monday morning Dees and Orbison played this early arrangement to Monument Records boss Fred Foster but he told them the song needed a “happy ending”, which the guys duly added with the ‘She’s walking back to me’ section. It wasn’t too long before Oh, Pretty Woman was being laid down in Foster’s Nashville Studio. 

The final version featured bass, piano, Bill Dees singing harmony vocals, two drummers, two sax players and three guitarists – Wayne Moss, Billy Sanford and Jerry Kennedy. Quite a bit of time was spent fine-tuning the arrangement including changing a few bars to 2/4 time so Roy could “catch his breath” and extending that guitar riff.

“They had a lick that his “They had a lick that his guitarist Billy Sanford had been working on and we were kind of working around that and changed it somewhat,” recalled legendary Nashville session man, Wayne Moss to Total Guitar. “It started off just as that, ‘Da da da da dow’ but we ended up playing ‘Da da da da dow da da da’ and that ended up being the lick on the record!”

The riff’s simplistic and wholly effective build-up was achieved by each guitarist successively playing the same thing. “There’s only one part, but as one guy played the riff, another would come in and play it,” explained Moss. “A guitar would add each time we were trying to build it. Then one of them played the tremolo in the bridge part, but I don’t remember who that was… but I just waited for that lick to come up. Roy Orbison had a 12-string with him and you don’t hear a lot of it on there, but he played one. I played a [Fender] Jazzmaster and a Gibson amp, which is what I generally did with Roy. 

"The other two guys had different kinds of guitars. Jerry Kennedy had a red Gibson and I don’t remember what Sanford was playing, but the combination sounded good.”

If you can play a whole bunch of notes in a row, really complicated and real fast, I don’t think it proves as much as playing something you can go down the road humming or whistling

Wayne Moss

As far as mid-'60s Nashville sessions go, Oh, Pretty Woman took a long time to cut with a total of three hours accrued to nail it plus another half hour to record its B-side, Yo Te Amo Maria. Union rules for session musicians were strict and if recording time exceeded a three-hour limit, then overtime rates would come into play. But aside from the extra pay, the guys playing on this particular session were more than happy to carry on as they could all sense the track’s hit potential.

“It was an exceptionally long time to spend on one song,” says Wayne. “But I think the producer [Fred Foster] and Roy and everybody involved knew that it was gonna be a hit record, so we were gonna take the time to get it right. We could just feel the magic in the studio and everybody was lighting up. It had a good driving beat to it and it just started to sound like money, you know? We all knew we were onto something.”

When Total Guitar asked Wayne Moss why he thought the Oh, Pretty Woman guitar riff has been so oft-played and loved by successive generations, he didn't hesitate with his answer. “If you can play a whole bunch of notes in a row, really complicated and real fast, I don’t think it proves as much as playing something you can go down the road humming or whistling. It’s repetitious and just one of those things that’s easy to relate to.”