TROUBADOUR: I’ve been the town troubadour for six months now, and I think I’ve done a pretty good job and then, he shows up (points to other troubadour).
RIVAL TROUBADOUR: Hey.
TROUBADOUR: And there’s no room for a second troubadour in Stars Hollow.
Even though we’ve only seen the Town Troubadour since That Damn Donna Reed, which took place in February, he’s actually been in town since early November at least. We learn that the Troubadour is a real man of mystery, as we don’t know how he supports himself. He doesn’t play music in the streets for money, even refusing it when offered.
Nor do we know where he lives: he is never shown shopping or eating at the diner, and nobody seems to know anything about him, so he isn’t a regular part of the town. On the other hand, we never see him driving, cycling, catching a bus, or even walking home, so we don’t know where he goes when he finishes playing music in Stars Hollow. This is all part of the “mystique” that he believes troubadours are meant to have.
Is he even human? Is he an angel, or a spirit from the stars, sent to bring music to Stars Hollow? Is he from another dimension, or the real Grant Lee Phillips able to project himself somehow into the Gilmore Girls universe? These questions will never be answered.
His role seems to be to guide people’s lives through song, and to help them learn to express emotions – all part of Stars Hollow being a place where love can be nurtured and developed. Later in the scene, Rory stands up and says that the Troubadour is able to express how the townspeople feel through his songs, and to say what they are thinking. This certainly seems to be case in this episode.
(Interestingly, the Troubadour only seems to have come to Stars Hollow when Rory had begun dating Dean, and Lorelai had begun dating Max. Did their love affairs attract him to the town, as if they now needed his emotional guidance?)