Matthews later 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). The monkey metaphor would eventually see later use in songs like "Big Eyed Fish" and the unreleased "Monkey Man".
While the song was a staple of Matthews's tours with Tim Reynolds until 1999, the song remained one of the rarer tracks to appear in concert with the full band after 1995, though it did see some play during the main tours by the band until 1999 as well. After that, it was played very sparingly, except for appearances at some shows in the summer of 2002. However, the addition of Rashawn Ross as a regular guest artist to the band's tours in 2006 resulted in the return to the touring rotation of a number of songs of which brass instruments were a key component; one of which was "Proudest Monkey", and the song enjoyed its most exposure in a full band setting since 1995.