Her reputation was confirmed when Kurt Cobain's diaries were posthumously published in 2002 included this mention: "Call Nan Warshaw" appears on his to-do list.

[7] While having drinks at a bar, Warshaw, Miller, and Babcock made a wish-list on a cocktail napkin of unheralded Chicago bands and musicians they loved[9] — who all had a thread of old school country running through their music.

[10] The album included artists such as The Bottle Rockets, Freakwater, The Handsome Family, and Robbie Fulks, as well as The Sundowners,[6] a country music trio that started in the 1950s.

In 1997, singer and Bloodshot Records artist, Kelly Hogan was the first paid employee, working as the label's publicist.

allowed Warshaw and Miller to dedicate themselves full-time to running the label, move to a bigger office space in the northwest side of Chicago, and begin to hire employees.

The Chicago twang, country, and punk scene, often described as a sort of an anti-Nashville, continued to expand, often led by various projects involving The Mekons' Jon Langford.

[25] Starting in the mid 1990s, Bloodshot hosted a free barbecue-and-music day-long showcase at both Austin, Texas' SXSW and New York City's CMJ music festivals.

A month later she announced that she was not just stepping away, but resigning, with Miller to continue the work of running the label with Warshaw still retaining 50% ownership.

[30] In mid-July 2020, after an internal audit, Bloodshot Records staff issued a statement further accusing Warshaw of long-term negligence in regard to royalty payments and accounting.

Warshaw said, "This passing of the torch ensures that the legacy of nurturing and celebrating unique indie music will live on.

Some of the early artists who started out on Bloodshot went on to sign with larger major record labels, specifically Old 97's and Ryan Adams.