Introduction
Willie Nelson’s 1965 performance of a “Hit Medley” on the Grand Ole Opry holds a special place in the history of country music. At that time, Nelson had yet to adopt his now-iconic long hair and headband look. Instead, he presented a clean-cut image, dressed in a formal suit, performing without his guitar, Trigger. The medley featured a collection of his early hits, including “Funny How Time Slips Away,” “Crazy,” and “Hello Walls.” These songs had already gained significant popularity and were featured on his debut album, …And Then I Wrote.
This performance came at a pivotal time in Nelson’s career. Though he was gaining recognition as a songwriter, particularly for hits penned for other artists like Patsy Cline’s rendition of “Crazy,” he was still struggling to achieve mainstream success as a performer. The 1965 medley showcased his songwriting prowess and emotional depth. His rendition of “Crazy,” in particular, struck a chord, as Cline had tragically died just two years earlier. Nelson’s performance was poignant and heartfelt, a tribute to their collaboration.
Audiences watching this Grand Ole Opry appearance might have been surprised by the contrast between the polished appearance Nelson had in 1965 and the rugged, outlaw image he would later embrace in the 1970s. Nonetheless, even without his signature style, his songwriting talent and emotive delivery were unmistakable.
This medley is an important snapshot of Nelson’s early career, demonstrating his undeniable impact on the country music landscape, even before his transformation into an “outlaw” figure of the genre.