In April 1990, when Phish performed "Uncle Pen" at the Woodbury Ski & Raquet Club, they were in the early stages of their career, having just released their sophomore studio album, "Lawn Boy," in 1990. This album marked a significant step in the band's evolution, showcasing their unique blend of rock, jazz, bluegrass, and progressive music. "Lawn Boy" included fan favorites like "Bathtub Gin" and "Lizards," but it was during live performances, like the one captured in the "Live and Outdoors - Phish" VHS, that the band really began to develop their improvisational prowess, which would become a hallmark of their live shows. This period was crucial, as Phish was establishing a dedicated fan base and honing their craft, setting the foundation for their future as an influential jam band. The choice to perform "Uncle Pen," a Bill Monroe cover, reflects their appreciation for bluegrass roots, further illustrating their eclectic musical influences.