The band arrived two hours late for the concert due to becoming lost on an alternate route they were forced to take when a snowstorm struck.
As a result, the band jammed the music that would later become "Proudest Monkey" to test their equipment, with Matthews making up lyrics on the spot.
Matthews kept that experience in mind when reworking the lyrics to the song, establishing the image of the monkey as a metaphor for the entrapment he and the band were feeling at the time (both the literal, in being trapped on a bus in the snowy mountains; and the symbolic, in being trapped in a seemingly endless cycle of repetitive performing, and thus feeling limited in their music).
After a number of teases and partial performances, "Proudest Monkey" debuted proper on December 29, 1994 during a show at the Grady Cole Center in Charlotte, North Carolina, albeit with unfinished lyrics.
The song would make appearances at shows throughout 1995, gradually evolving into the extended jam form that it would take when it was recorded for Crash.