In comes an intro that isn’t messing around… Sturdy, confident drums… Then Dun-dun-dun-dun-dun… An intro that builds – a layer added with every repetition – until it morphs into a chain-link of a riff.

Oh, Pretty Woman, by Roy Orbison (his 3^rd and final #1)

2 weeks, from 8^th – 22^nd October / 1 week, from 12^th – 19^th November 1964 (3 weeks total)

And then in comes that voice. The Big O. Reigning it in a little compared to his last, full on operetta of a #1 single, ‘It’s Over’. Pretty woman, Walkin’ down the street, Pretty woman, The kind I’d like to meet…  Now, let’s pause for just a second. That ‘I’d’ right there, twenty seconds in, makes or breaks this song. ‘I’d like to meet…’ suggests that he’s been a little unlucky in love. Make it ‘I like to meet…’ as some sources do claim, and the singer suddenly becomes a player, a predator, and the song a little icky. I’m going to trust that it’s an ‘I’d’…

Anyway. Roy’s just hanging out, chilling, watching the girls go by. Pretty woman… I don’t believe you, You’re not the truth, No-one could look as good as you… And then a spoken Mercy! that is truly sublime. Pretty woman, Won’t you pardon me, Pretty woman, I couldn’t help but see… That you look lovely as can be, Are you lonely, Just like me…? He may be ogling and approaching passers-by, but he’s a perfect gentleman about it. Plus, he’s lonely. There’s a tenderness to this song that lifts it above other stalker-anthems like ‘I’m Walking Behind You’ and ‘Every Breath You Take.’

Then, though, Roy does something that even he probably can’t get away with. The grrrrrooooowwwwllllll. Let’s pretend the growl never happens, OK? We get to the bridge – a real fifties rock ‘n’ roll throwback – that seals this record’s place among the greats. Pretty woman, Stop a while, Pretty woman, Talk a while… while the drums roll, and a piano tinkles.

As with ‘It’s Over’, ‘Oh, Pretty Woman’ stands out against the musical landscape of 1964. It could have been a hit five years earlier, or ten years later. I’m not sure you could say the same of ‘Do Wah Diddy Diddy’. The Roy Orbison renaissance (the Roynaissance, if I may) of ’64 is probably the most pleasant surprise in a spectacular year of pop music. Though to be honest, he hadn’t been anywhere, and had been scoring big hits throughout the early sixties. It’s just that none of them had made it to the top of the charts.

We get to the climax of the song, and an already brilliant song is elevated even further. The rules of pop music never applied to Roy Orbison, and he bends them to great effect here. He serves us a cliff-hanger, similar to the one he dishes up at the end of ‘Running Scared’. The woman doesn’t stop, and he’s left disappointed. He slows it down, in his trademark talking-singing-freestyling style: Don’t walk away, Hey…. OK… If that’s the way it must be, OK… Then another moment of perfection – But, wait… Cut to the same drumbeat that opened the song. What’s that I see…? She’s turned around. She’s coming back! Of course she’s coming back. Was there a woman alive who could resist the Orbison charm?

I, as I’m sure you’ve realised, love this record. It’s a Rolling Stone Top 500, Rock n Roll Hall of Fame kind of record. A song that nobody can say a bad word about. I love Roy Orbison too, and still remember getting his greatest hits as a Christmas present back as a kid. Perhaps with the exception of Elvis, no other star of the fifties and sixties had an identifiable image like Roy Orbison. Dark suit, dark glasses, guitar, quiff. It’s up there with Michael Jackson’s hat and glove, and Madonna’s pointy bra. You may think it’s superficial; but it’s a hallmark of the very best pop stars.

Following this, Orbison suffered some pretty lean years in terms of chart hits, and some unimaginable tragedies: he lost his wife and his two eldest sons in the space of two years. But, as with all the greats he came back – The Travelling Wilburys, ‘You Got It’ and all that. And then, just as his comeback was picking up speed, and in a twist befitting one of his greatest ballads, he had a heart-attack and died, in 1988, aged just fifty-two. He’s a legend – plain and simple. The songs that defied convention, the operatic voice, and the dark glasses. The Big O.