A jam band coming out of the Midwest in the mid-'90s, Umphrey's McGee edged toward the Frank Zappa side of the improv ock scale, as opposed to the Grateful Dead/Allman Brothers Band direction espoused by many of their contemporaries, like the Big Wu. The members of Umphrey's McGee met at the University of Notre Dame in South Bend, IN. The original four bandmembers (keyboardist Joel Cummins, guitarist Brendan Bayliss, bassist Ryan Stasik, and drummer Mike Mirro) had been playing in various campus bands when they got together in December 1997, naming themselves after a cousin of Bayliss. With the national jam band infrastructure already in place, the band quickly began disseminating their live shows and soon released their first album, Greatest Hits, Vol. 3. The fourth-generation jam band often included songs by Phish and moe. in their live sets, along with the usual selection of wacky covers.

The quartet won a large following in the South Bend area. As bandmembers graduated, the group instated a more and more rigorous rehearsal schedule. Half of the band had degrees in music, so emphasis was placed on constant precision. The band religiously studied tapes of their performances in order to improve them. While their record sales never reached high levels, they used live recordings to pave the way for gigs in parts of the country they'd never been to before. A story circulates of the band selling out shows in Colorado before their first trip there due to the distribution of live CDs. In 1999, the band released a live recording, titled Songs for Older Women, their first recording to feature percussionist Andy Farag. In 2000, the band became a sextet with the addition of guitarist Jake Cinninger, a former member of a fellow South Bend group Ali Babba's Tahini, which had broken up, and they made the move to the bustling metropolis of Chicago. From their new home base, the band went on two-week jaunts throughout the Midwest, occasionally hitting other markets and sharing the stage with a variety of musicians, including Dr. Didg (aka Graham Wiggins), the Chicago-based lues harmonica player Sugar Blue, Béla Fleck, Topaz, and many others.