The Stars Hollow Troubadour was a staple in the rich fabric of Gilmore Girls. The Troubadour, played by Grant-Lee Phillips as himself, appeared in 19 episodes of Gilmore Girls between 2001 and 2007. Grant’s first appearance was on "That Damn Donna Reed", and his last appearance was for "Hay Bale Maze".
During his stint on Gilmore Girls, Grant-Lee Phillips performed: "Beautiful Dreamers", "Heavenly", "Lily A Passion", "Mona Lisa", "Sadness Soot", "Smile", "Spring Released", and "Sunday Best". Grant Lee Buffalo songs featured on the show include "Everybody Needs A Little Sanctuary", "Honey Don’t Think", "It’s the Life", "Mockingbirds", and "Truly, Truly." This video segment includes all of the songs that Grant-Lee Phillips performed as the Stars Hollow Troubadour on Gilmore Girls:
Grant-Lee Phillips began his career in the acclaimed group Grant Lee Buffalo with their debut album Fuzzy in 1993. The band reached an impasse in 1999, when Grant-Lee Phillips struck out on his own as a solo artist. Grant-Lee is both a singer and songwriter and multi-instrumentalist known for his dexterity on the acoustic twelve-string guitar. His most recent albums include Nineteeneighties from 2006 and Strangelet from 2007.
As if the world were not small enough, Grant-Lee Phillips created the original score for The Return of Jezebel James! I haven’t been able to find any video files featuring the score, so if you do, let me know!
Sources: grantleephillips.com, imdb.com, wikipedia.org