"Uncle Pen" is a song written by Bill Monroe about his uncle and musical mentor, Pendleton Vandiver. Besides Monroe, the song was recorded by Porter Wagoner in 1956, Goose Creek Symphony in 1971, Michael Nesmith of "The Monkees" in 1973 on his solo album Pretty Much Your Standard Ranch Stash, and Ricky Skaggs in 1984. "Uncle Pen" was Ricky Skaggs' ninth number one single on the country chart. The single went to number one for one week and spent a total of thirteen weeks on the country chart. Bill Monroe played a character named "Uncle Pen" disappointed at the citification of Ricky Skaggs in the 1985 video for "Country Boy". The improvisational-rock band Phish has performed their cover version of Uncle Pen over 200 times in the band's 30-year career.

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