‘Gilmore Girls’: 1 Supporting Actor Felt Like They Were Playing a ‘Cartoon Version’ of Themselves

The fictional world of Stars Hollow, Connecticut, wouldn’t be complete without the town troubadour. Played by singer-songwriter Grant-Lee Phillips, the town troubadour added some small-town charm to the place Lorelai (Lauren Graham) and Rory Gilmore (Alexis Bledel) called home. One of the many supporting actors on Gilmore Girls, Phillips felt he played a “cartoon version” of himself. 

Grant-Lee Phillips joined the ‘Gilmore Girls’ cast as the town troubadour in 2000

Alexis Bledel as Rory Gilmore, Lauren Graham as Lorelai Gilmore
Alexis Bledel and Lauren Graham on Gilmore Girls | Mitchell Haddad/CBS Photo Archive via Getty Images

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Phillips joined the Gilmore Girls cast during season 1. According to his IMDb credits, he made his debut in Gilmore Girls Season 1 Episode 16: “Star Crossed Lovers and Other Strangers,” performing an acoustic version of his song, “Heavenly.” From that point on, Phillips would occasionally provide musical breaks in between scenes. 

Don’t get this Phillips confused with Sam Phillips. The latter Phillips is the musician responsible for the “La La’s” on Gilmore Girls. Town troubadour Phillips said as much on Twitter in March 2020. Both singer-songwriters just so happened to work on the same TV show and have identical last names.

Phillips performed in 13 episodes total throughout seven seasons of Gilmore Girls. He played covers of songs such as Wham!’s “Wake Me Up Before You Go-Go,” Cat Stevens’ “Peace Train,” Paul Simon’s “Me and Julio Down By The Schoolyard,” and The Beach Boys’ “Be True To Your School.” 

Although he only appeared in just a fraction of the show’s episodes — Gilmore Girls had 150-plus episodes — Phillips’ turn as the town troubadour became a memorable fixture in Stars Hollow. So much so, the writers behind Gilmore Girls included a storyline about him having competition. Phillips went on to reprise his role in 2016’s Gilmore Girls: A Year in the Life

The singer-songwriter sees his ‘Gilmore Girls’ role as a ‘cartoon version’ of himself

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During a 2020 interview with Variety marking the show’s 20th anniversary, Phillips reflected on his town troubadour role. He explained that what fans of Gilmore Girls see on-screen isn’t the real him. 

“I think of it as being sort of a cartoon version of myself,” he said. “I always got a kick out of the fact that it seemed as though my character was always worked up about something.” 

In Gilmore Girls Season 1, the town troubadour didn’t appreciate it when another person tried to replace him. The situation was resolved at a town meeting when Phillips’s character became the town’s official town troubadour. However, he ended up performing a duet with his competition. 

Phillips continued, suggesting that having his “turf” threatened may have contributed to the town troubadour’s demeanor. 

“It might have to do with some other troubadour treading on my turf — a war with my sister played by Louise Goffin,” Phillips said. “But I wondered, ‘What am I projecting that they keep writing all of this anger into my character?’”

Goffin is the daughter of Carole King, the musician who sings the Gilmore Girls theme song, “Where You Lead.” In fact, Goffin sang backup vocals on the track when it was re-recorded for the show in 2000. She made a cameo in the Netflix revival alongside Phillips. Goffin sang part of her song, “Archives,” before Phillips chased her away. 

The biggest challenge playing the town troubadour on ‘Gilmore Girls’ involved walking fast while playing guitar slowly

Playing the town troubadour’s not as easy as it might appear on Gilmore Girls. Phillips sang, played the guitar, and sometimes the harmonica, all while walking through the streets of Stars Hollow. Multitasking wasn’t necessarily the hardest part. Doing things at different speeds Phillips found particularly difficult. 

“For me, the challenge was when I had to strum a little slower—and walk a little faster,” he told Salon during a February 2016 phone interview. “That involves good coordination. That was my challenge: walking faster, strumming a little slower.”