“Celebrating their first anniversary of music”
They really need to learn how to enjoy their work.
Jesse Wagner & Jillian Todd AKA: Jess & Jill – “Celebrating their first anniversary of music”
The hottest duo in Key West, Jess & Jill, is a Gen Z – Gen X mashup of talent that really works. These two artists bonded in a unique way through a fairly obscure Bob Dylan song. On August 18, 2023, they were performing a gig with Gary Hempsey at Schooner Wharf Bar. Jesse called for “Tangled Up in Blue”, a Dylan song from his Blood on the Tracks album. It’s a folksy song that takes the listener on a long journey of two lovers. Jillian always loved the song and crept into the vocals a bit. Jesse gave her a look and they both felt something at the same moment – their voices harmonized beautifully, it was very special.
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They almost immediately scheduled a gig together knowing they had tapped into something. Both of them felt music with the same passion and heart. Their voices and instruments blended in a special harmony – they approach their music like one musician.
Their duets have become a primary focus for both of them. Their shows include Dylan, Grateful Dead, Joni Mitchell, folk covers, all sprinkled with their own creativity and harmony. Naturally, both of them have been writing originals that express a deep heartfelt love of music.
Their musical journeys are different and yet, similar. Jillian Todd was born in 1999 near Potsdam, New York, in the foothills of the Adirondack mountains, close to the Canadian border. At age 6, she began taking piano lessons from a really cool hippie lady who lived across the street.
Her father, Ben, played guitar in an 80’s rock/country cover band along with his day job. Her mother Alisah played piano. Music was how her parents met while in college. “Mom has the perfect Janis Joplin voice”. Her sister, Shannon, says “Mom’s voice is like a picture of a rose with a scratch through it.”
Gary Hempsey taught Jillian some fairly complex guitar techniques and was surprised a couple of weeks later to see she had mastered them so quickly.
Jesse is the most experienced part of the duo and a master guitarist.
Jesse Wagner was born in 1977, he considers himself a Xennial. A micro-generation between 77-83 when the original Star Wars trilogy was released. They learned how to research in a physical library. They owned cassettes, CDs, and an MP3 players and were among the first to use a personal computer in school. He was raised in Montgomery County, Pennsylvania, located between Allentown and Philadelphia. He considers himself part of the “Philly Mafia” of the Key West music scene along with Gary Hempsey, Ross Brown, and several others.
Around 1985, Jesse’s father started teaching him to play the guitar and where he first learned the Beatles’ music. His mother was a folk guitarist in the 60s and 70s. His “prettiest” high school teacher encouraged his vocals and he joined the chorus. He also learned harmony and music structure. His grandmother, Betty Jean Wagner, took him to a Willie Nelson concert while he was in high school. It convinced him to perform music live.
Jesse and his band, Happy Dog, frequented Key West and in 2011, they decided to stop leaving. Jillian graduated from college and accepted a season contract at the Waterfront Playhouse in 2021. She was encouraged by her new friend Belle Jampol, to buy a guitar a sing. She practiced a few songs, and started busking on Duval Street and Mallory Square on her days off. She connected with Gary Hempsey and was invited to perform with That Hippie Band on Earth Day in 2023 and again in 2024. Jillian topped off an amazing year with a sold out two-day solo show in March 2024 at the Tennessee Williams Cabaret Theatre.
Performing their signature song by Bob Dylan “Tangled Up In Blue”
This past July, Jesse and Jillian traveled to the Grateful Hotel located in Playa Grande, a beach village in the province of Tamarindo, Costa Rica. The hotel has a cool rootsy Grateful Dead theme. Jesse’s long association with other deadheads tipped him off to the hotel resulting in the week-long gig. There were murals, mosaics, and direct quotes of Jerry Garcia adorning the hotel walls.
Costa Rican culture promotes unity with nature and that was definitely evident at this place. The food at the hotel restaurant, Sugaree Bar & Grill, was phenomenal. The dishes were creative and the fresh ingredients superlative.
The hotel was completely booked with a crew of their friends. It felt like a week-long family celebration with no drama. They would explore Costa Rica by day and at night, their friends gathered to hear the duo sing. They would love to return next year for two weeks.
Jesse hasn’t been inspired to write music for a while but this new collaboration has resulted in a number of new original songs by the duo. They are adding original songs to shows and are writing and recording for a potential new album. They recently debuted new originals “Abreast at the Bow”, “Blue and Rolling”, “Apples and Piper Green” at a Green Parrot Sunday show. Some of their newer songs have what they term, a unique “modern-antique blues” style. They’re theatrically melodic like something you would hear in an old movie.
To Jillian, Key West is 100 miles off the mainland, yet has a cosmopolitan feeling, and a strange sense of egalitarianism and peace. 
She knows there is magic here. Everyone talks about Key West like it is an animate being. She just seems to “get” Key West in a very soulful way and trusts this island.
Jesse has been here longer and got a few pointers from some of the older performers. 
He likes many of the newer performers in Key West and says many are making music that is original, with heart, and often is not derivative of any particular group or genre – it’s Key West inspired. Don’t miss a chance to hear this amazing duo.
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