Roy Orbison's 'Oh, Pretty Woman': From Chart-Topper to Landmark Copyright Case (2025)

On October 8, 1964, Roy Orbison's "Oh, Pretty Woman" Dominated the Charts and Later Sparked a Game-Changing Legal Battle. The song wasn’t just a massive hit—it became a cultural milestone with a lasting impact far beyond music. But here’s where it gets controversial: decades after topping charts worldwide, it became central to a pivotal federal copyright lawsuit that reshaped how parody is protected in the United States.

On this very day in 1964, Roy Orbison held the number one spot on the UK Singles Chart with "Oh, Pretty Woman." This success marked his third song to reach the summit in the UK and it remained there for three consecutive weeks. Across the Atlantic, it was his second and final number one hit on the US charts, cementing Orbison’s place in music history. Yet, the journey of this iconic track extended well beyond its commercial triumph.

Co-written by Orbison and Bill Dees, "Oh, Pretty Woman" was released on August 15, 1964, quickly capturing global audiences. It achieved number one status not only in the US and UK but also in countries like Austria, Belgium, Canada, Ireland, New Zealand, Norway, Singapore, Switzerland, West Germany, and even Hong Kong. Such widespread acclaim is a testament to the song’s universal appeal.

The inspiration behind the song’s catchy opening lines is a charming story: during a songwriting session, Orbison’s wife Claudette announced she was stepping out for some errands. When Orbison asked if she needed money, Bill Dees chimed in with the phrase, "Pretty woman never needs money." Those words sparked Orbison’s imagination, and he began singing the famous opening melody almost instantly.

Bill Dees later shared, "We wrote 'Oh, Pretty Woman' on a Friday, recorded it the following Friday, and by the next Friday, it was released." This rapid creation and release schedule is remarkable, especially considering the track’s enduring influence. That influence can still be felt today, as the song features prominently in film and television, most notably in the 1990 romantic comedy Pretty Woman.

But here’s the part most people miss: this song also played a surprising role in shaping federal copyright law in the US.

More than two decades after Roy Orbison first enraptured audiences, a new chapter in the song’s legacy began. A year following Orbison’s death, the rap group 2 Live Crew crafted a parody of "Oh, Pretty Woman" for their album As Clean As They Wanna Be—a censored version of their notorious As Nasty As They Wanna Be. This parody did not go unnoticed. Acuff-Rose Music, which held the song’s publishing rights, sued 2 Live Crew, setting off a legal battle that would ascend all the way to the United States Supreme Court.

This case sparked intense debate about the balance between intellectual property rights and freedom of expression. Ultimately, the Supreme Court ruled in favor of 2 Live Crew, affirming that parody constitutes fair use under copyright law, alongside criticism and commentary. This landmark decision was groundbreaking because it protected parodic works in music, film, and other creative media, fostering greater artistic freedom nationwide.

Isn’t it fascinating that a chart-topping hit from the ’60s could later become the centerpiece of a case that fundamentally changed how we understand creativity and legal boundaries today? What do you think—is parody essential for art’s evolution, or does it sometimes cross the line? Share your thoughts below and join the conversation.

Featured Image by Evening Standard/Getty Images

Roy Orbison's 'Oh, Pretty Woman': From Chart-Topper to Landmark Copyright Case (2025)
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