Recording and Production
Marshall recorded Dear Sir in December 1994 in a small basement studio near Mott Street in New York City at the same time she recorded Myra Lee (1996), which was released nearly two years later, with guitarist Tim Foljahn and Sonic Youth drummer Steve Shelley; Marshall and Shelley had initially met after she played a show opening for Liz Phair in 1993. A total of 20 songs were recorded in a single day by the trio, all of which were split into two records, making up Dear Sir and Myra Lee.
According to Foljahn, the recording session was "mellow" and "quick", and he referred to their recording space— purportedly a moist basement lined with musical equipment and empty beer cans— as "literally the third subbasement. It was so New York". Contrarily, Marshall described the recording session as "anxiety-ridden". "Most of the time Steve and Tim ended up looking at each other like, "What do we do"?" said Marshall. "I wasn't sure what to tell them since I had never really written songs with a band in mind."
Although Dear Sir is considered Marshall's debut album, she expressed herself in a 1996 interview that she considered it an EP. The original 1995 release of the album by Runt Records featured a total of only eight tracks; however, the 2001 re-issue by Plain Recordings featured the addition of the song "Great Expectations", giving the album a total of nine tracks (note that another version of the song "Great Expectations" is also featured on Cat Power's second album, Myra Lee). Both versions of Dear Sir end with the song "Headlights", which is a re-recording of an early song by Marshall's first backing band, and had priorly been released as a 7" single in 1993.
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