Billy Flynn isn’t just a guitarist; he’s a living conduit for the rich, electrified history of the blues. With five decades in the game, he’s earned his status as a first-call session master and a nuanced bandleader, known for his ability to perfectly conjure the sound of Chicago legends while maintaining a versatile, original voice. From the stinging West Side sound to swinging rockabilly, Flynn’s repertoire is as deep as his roots.
Let’s drop the needle on three essential tracks that define the breadth of his artistry.
Track Spotlight: Three Sides of Billy Flynn
1. “If It Wasn’t for the Blues” (from Lonesome Highway, 2017)
If you want to understand who Billy Flynn is, listen to this track. As a key cut from his celebrated Delmark Records debut, Lonesome Highway, this song is pure, unadulterated West Side Chicago Blues.
Here, Flynn’s guitar work is raw, piercing, and emotionally charged. It’s the sound of the master paying tribute to his mentor, the late, great Jimmy Dawkins. The track features a signature grungy tone and a heavy emphasis on feel over flash. It’s a powerful reminder that while Flynn plays with immaculate taste, he never forgets the emotional punch at the heart of the blues tradition. This is the sound of the ‘Lonesome Highway’ itself—a road well-traveled and deeply felt.
2. “Good Navigator” (from Lonesome Highway, 2017)
From gritty Chicago to swinging rock ‘n’ roll—that’s the turn Flynn makes with the rocking opener, “Good Navigator.” This track is a masterclass in versatility, showcasing his ability to fuse blues with early rock and roll.
The tone is bright, the rhythm is propulsive, and the playing is often cited by critics for its uncanny resemblance to the legendary Chuck Berry. Flynn sings a fantastic duet with guest vocalist Deitra Farr, trading lines in a call-and-response structure before he unleashes a fantastic, melodic solo. This song demonstrates that Flynn isn’t afraid to step outside the 12-bar box, using his deep knowledge of roots music to deliver something dynamic, joyful, and utterly infectious. He truly is a “Good Navigator” across the entire landscape of American roots music.
3. “Gimme Some of That” (from The Royal Treatment, 2006)
Though perhaps less discussed than his Delmark debut, the 2006 album The Royal Treatment established Flynn’s consistent quality as a bandleader and songwriter. “Gimme Some of That” is a testament to the fact that Flynn’s work has been essential for decades.
This track is a prime example of his work that touches upon his broader influences—a combination of classic blues, R&B, and soul. It showcases his ability to maintain a sharp, clean sound even within a complex arrangement. It’s solid proof that whether he’s lending his talents to others or commanding the stage himself, Billy Flynn’s tasteful playing and deep grasp of classic styles always shine through.
The Takeaway
Billy Flynn’s music is a historian’s delight and a blues lover’s treasure. He is the genuine article: a guitarist who can summon the ghosts of the West Side and then turn around and lay down a track that makes you want to dance, all within the space of a single album.
