A Lyrical Meditation on Dreams Out of Reach: The Enduring Poignancy of Roy Orbison‘s Late-Career Classic
There are songs that simply exist, and then there are those that carry the weight of memory, a bittersweet ache that time only deepens. “Windsurfer,” a gem tucked away on Roy Orbison’s magnificent, posthumously released 1989 album, Mystery Girl, belongs firmly to the latter category. Though the album’s lead single, “You Got It,” soared to the top ten in both the US and the UK—hitting a peak of US Billboard Hot 100 at No. 9 and UK Singles Chart at No. 3—and the album itself was a massive commercial success, peaking at No. 5 on the US Billboard 200 and No. 2 on the UK Albums Chart, “Windsurfer” never saw a single release and thus, has no chart history of its own. Its significance, however, is not measured in sales but in the quiet, profound melancholy it imparts.
Released on February 7, 1989, just two months after Orbison‘s untimely death in December 1988, Mystery Girl was a stunning testament to the enduring power of “The Big O’s” unique, operatic voice and emotional depth. “Windsurfer,” co-written by Orbison and long-time collaborator Bill Dees (who co-wrote classics like “Oh, Pretty Woman”), captures a nostalgic, almost mythical seaside wistfulness. The lyrics paint the picture of a lone figure—the windsurfer—sailing endlessly, “flying in the sun,” before coming ashore to write a single, heartbreaking question in the sand: “Why do we always go for something out of reach?”
The story behind the song adds a chilling layer of darkness to its gentle beauty. According to Orbison’s sons, the original iteration of the song was starkly different—an “overt suicide song” where the lonely windsurfer was found “face down in the sand.” Producer Jeff Lynne, one of the many superstar collaborators on Mystery Girl, heard the demo and loved the music but gently suggested to Orbison and Dees, “Does the windsurfer have to die?” The resulting re-write softened the tragedy, transforming a story of death into a more universal reflection on unfulfilled yearning and the pursuit of unattainable dreams. It is this final version, with its wistful ode to a solitary, endless summer and its profound question about the human condition, that we find on the album.
Musically, the track is a masterclass in late-period Orbison refinement. Produced by Orbison and Mike Campbell (of Tom Petty and the Heartbreakers), it features a shimmering, almost ethereal acoustic arrangement, anchored by Rick Vito’s exquisite, weeping slide guitar work. That slide guitar is the sound of pure, bottled-up longing, a fitting counterpoint to Orbison‘s voice, which, even in his final recordings, possessed an unparalleled vulnerability and power. Listening to it now, it’s impossible not to hear the ghost of a classic era in rock and roll, a man who, despite his own recent resurgence and creative energy, still carried the weight of past sorrows in every soaring vocal phrase.
For those of us who grew up with the dramatic, leather-clad figure behind the dark glasses, “Windsurfer” feels like a final, meditative sigh—a quiet moment of seaside reflection before the curtain falls. It’s a moment of clarity on the eternal human struggle: the desire for the things we can’t quite grasp, whether they are loves lost to time or dreams that forever hover just beyond the horizon. It’s a bittersweet farewell from a man who always understood the most profound kind of ache.