Initially the band concentrated on playing their own versions of classic blues songs, particularly electric Chicago-style blues, and performed their first concert at Phyllis’ Musical Inn in Chicago on October 29, 1998. The band quickly progressed from covering blues tunes to writing their own music. Their influences include the Allman Brothers Band, Free, Cream, Led Zeppelin, the Rolling Stones, and Humble Pie, in addition to blues artists such as Muddy Waters, Robert Johnson, and John Lee Hooker.

In 1999 the band met singer-songwriter Michael Connelly, who collaborated with them on their inaugural effort, the five-song EP Goin’ Back Home. The Steepwater Band returned the favor by performing on Connelly’s project, Bottles of Wine. Connelly officially joined The Steepwater Band in 2000. The years of 1999 and 2000 saw the band performing relentlessly in Chicago and the surrounding region. During this time they continued to write new material and hone their gritty guitar-based blues-rock sound. The buzz in the local music community increased and on June 8, 2000, The Steepwater Band performed at their first Chicago Blues Festival, kicking off that year’s event at high noon.

The band released its first full-length CD in 2001. Titled Brother to the Snake, the CD was released with the support of radio station WXRT and Jim Beam to a packed house at Chicago’s Double Door. During the year the band also released a live-in-the-studio album, Live…Half in the Bag. The band continued to play in the Midwest in 2002 and 2003, often being selected for opening act slots for international acts including Bad Company, 38 Special, The Fabulous Thunderbirds, Sonny Landreth, Buddy Guy, and Taj Mahal. The band also signed a recording, management, and publishing deal with Funzalo Records/Mike’s Artist Management during this period. This relationship resulted in the production of one album, Dharmakaya, which was recorded with producers Sean Slade and Paul Kolderie (Radiohead, Warren Zevon, the Pixies, Uncle Tupelo) in Boston and released on May 18, 2004. Connelly departed in October 2004, and the band and Mike’s Artist Management ended their relationship in early 2005.