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Childhood friend of Trey's from Princeton. Holloway co-wrote "Aftermath" with Anastasio, which appeared on The White Tape in 1986. The lyrics to both "AC/DC Bag" and "Wilson" reference Holloway. At the beginning of the second set on 4/14/93, Holloway got on stage and proposed to his girlfriend Jen. She said yes and the band performed "AC/DC Bag" in response to start the set. On 5/7/99, at a Trey Anastasio solo show, Holloway joined his old friend for the only known public performance of "Aftermath."