Simultaneously, the out there groove of the Garcia/Wales jamming - as captured on the Side Trips Vol. I CD - plus the open-ended Dark Stars and other like-minded explorations, primed me with open ears to absorb the late 60's/early 70's electric Bitches Brew style jazz of Miles Davis. As you probably know, a discovery of Miles Davis can be a home base of its own leading in all kinds of interesting directions, the most rewarding of which may be a step back in time to explore the history and roots of jazz, or a leap forward to check out more modern practitioners such as Medeski Martin and Wood or Bill Frisell.
It was the Jerry Garcia Band that I would see first, at the Richmond Coliseum in 1993, completely naive to the scene. Then, in the summers of 1994 and 1995, I got to see the Grateful Dead a handful of times before Garcia's passing. From that fleeting glimpse, I was made hip to the power of live music, which segwayed symbiotically into the peak of the jamband movement, coinciding with many crazy nights enjoying the likes of Phish, moe., Leftover Salmon, Yonder Mountain Stringband, and - dare I say - String Cheese Incident.
When I finally started to play music with a focus on the melodic instrumental tunes of Ireland and Appalachia, it wasn't clear to me if this interest stemmed from something I had listened to previously or from some other motivating factor. This music was just far enough removed to lessen the intimidation factor and allowed me to learn to "pick" without having to be in the direct shadow of any known musical heroes. A song of my own, in other words. But what at first seemed unrelated may have a connection after all. There's a melodic continuity in Jerry's improvisations and a link to old-timey music that you can really hang your hat on.
The Jerry Garcia songbook is basically the American songbook, and it's definitely worth looking into from the perspective of a player as well as a listener.