"#41" was originally written by Dave Matthews as a reply to lawsuits brought forth by Ross Hoffman, a former associate and manager of the band. Hoffman owned rights to a number of the band's songs in the early 1990s; however, due to creative differences, he was eventually fired by the band, and the band's present manager, Coran Capshaw, was hired. As an owner to the band's songs, Hoffman felt he deserved a share of the profits, which later caused a legal dispute between him and the band. Matthews wrote the song based upon the broken-hearted feelings he was experiencing as he was going through legal disputes with a former mentor of his.

On April 7, 1995, "#41" debuted under the title "41 Police." As the band had not come up with an official title for the song, the number 41 was used as it was the band's 41st song, and it sounded similar to a song by The Police, "Bring on the Night". The original performance was played at Cameron Indoor Stadium at Duke University, and lasted around nine minutes. This version of the song was played a total of 19 times before evolving into the "#41" that exists today.

In fall 1995, the song was officially named "#41" after several lyric and chord changes were made. This song was the band's fourth "numbered" song at the time, following "#34," "#36," and "#40." After "41 Police" became a defunct song, the first performance of the "#41" live was played on October 4, 1995 at the Tinker Street Café in . The show featured frequent collaborator Tim Reynolds on the electric guitar. In the fall of 1995 the band, along with Reynolds, recorded the song in the studio for the album Crash with producer Steve Lillywhite. On the album, a flute bridge by LeRoi Moore segues the song into the following track, "Say Goodbye," and was often played in this fashion during live shows after the song's debut. During that year, "#41" became the most played song on their summer tour.

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