The Walden Jazz Band was Jeremy Shatan and Michael Diamond's first foray into the performing arts--although the line-up that featured them was actually the band's second incarnation. The original line-up consisted of Amy Burton on vocals, Jeremy's brother Greg Shatan on saxophone, Matt Penn on drums, Dave Chalat on guitar, and Joe Chalat on bass. Stan Free, composer of the early synthesizer hit "Popcorn" was the group's music director and vibes player.

The original Walden Jazz Band played together from 1975 to 1976, during which time they played at least one full-length concert and one or two songs at the occasional Walden School assembly. When most of the musicians graduated in 1976, the Walden Jazz Band folded.

In 1978, the Walden Jazz Band reformed with new band members under the guidance of a new music teacher at Walden named Phil. Following in the footsteps of his older brother, Jeremy Shatan signed up to be the band's piano player. He was joined by Leo Shapiro on trumpet, Evan, a guest musician from St. Ann's School, on bass, Phil on saxophone, and Michael Diamond on drums. By signing up to be a part of the jazz band, an elective part of their education at Walden, the musicians promised that they would set aside time to meet and practice once or twice a week throughout the school year. These practices were held with the end goal of perfecting a couple of jazz selections, which would later be performed before an audience at the school's annual talent show, "A Musical Evening at Walden."

In an October 2005 interview with Beastiemania.com, Jeremy Shatan recalled that in addition to performing with the Walden Jazz Band, he had the honor of being the master of ceremonies for "A Musical Evening at Walden" in both 1978 and 1979. When asked what he recalled of these historic nights in musical history, Shatan replied, "I recall that I wore a gold lame jacket and that we played two jazz classics. One was 'Watermelon Man' by Herbie Hancock and the other was 'Mercy, Mercy Me' by Joe Zawinul."