After “Only the Lonely” netted Roy Orbison his first hit in 1960, nearly all of his subsequent singles followed the same template: rock and roll arias of rejection and loneliness showing off his epic range and vibrato. But unlike contemporaries who continued to churn out rehashed versions of their Big Hit to diminishing returns, Orbison’s formula never grew stale, both because of the consistently high quality of the material and because he was the sole occupant of his niche. No one else in the charts had a voice with the power and the pathos of Orbison’s; no one else could blend classical structure with pop without sounding gimmicky or pretentious.
Yet “Oh, Pretty Woman,” Orbison’s biggest hit, appears at first blush to be a far cry from heartrending ballads like “Crying” and “It’s Over.” The ornate orchestral instrumentation of his previous hits has been subbed with a straightforward rock and roll set-up reminiscent of his days at Sun Studios. The tempo is upbeat, and Orbison, for once, seems to be having fun. (If you remember one thing about the song, it’s the loping guitar riff. If you remember a second thing, it’s the endearingly cartoony growl after “No one could look as good as you.”) But strip away the snappy drums and the tongue-in-cheek machismo, and what’s left behind is a clearly-identifiable product of the saddest voice in pop.
Thematically, “Oh, Pretty Woman” is “Running Scared” played as romantic comedy: boy falls for girl, boy appears to have lost girl, girl surprises boy by coming back for him. (It’s a scenario that would have personal resonance for Orbison: he and his wife Claudette divorced as a result of her infidelity, then remarried the following year.) The lyrics are littered with references to being rejected and ignored. “Are you lonely just like me?” Orbison asks, before begging, “Pretty woman, don’t make me cry/Pretty woman, don’t walk away.” Finally, he resigns himself to his status as the man who too sensitive to be loved: “If that’s the way it must be, OK/I guess I’ll go on home, it’s late.”
Contrasting an upbeat melody with secretly morose lyrics has become a tired cliché in the wake of lesser artists using it as shorthand for depth. But the juxtaposition works in “Oh, Pretty Woman,” largely because Orbison is so convincing in the persona of the lovesick loner with the painfully sincere voice. And because it strikes at the ambiguity lurking beneath all the best love songs: how thin the line dividing love and loss, how arbitrary the distinction between acceptance and rejection. 8
Hit #1 on September 26, 1964; total of 3 weeks at #1
118 of 989 #1′s reviewed; 11.93% through the Hot 100