To play wavering, keyboard heavy music in mid-90s Seattle was no small feat, Jessamine were swimming against a flannel tide. Guitarist Rex Ritter moved to the Pacific Northwest from Ohio (where he played in a band with his brother who contributed drums to some of the early Jessamine recordings) and met up with keyboardist Andy Brown and bassist/singer Dawn Smithson.
As it was noted in the Nov. 15, 1994 issue of The Stranger;
After signing on the dotted line and getting some recording equipment, the band recorded over the course of three months with the band rehearsing, taping and playing live shows to hammer down the material before finishing basic tracks in two days.
The self-titled Jessamine debut album came wrapped in translucent paper and received accolades in the press.
The Lizard magazine note that
And as Dave Segal recognized "even though they peddle massive doses of distortion and flirt with chaos, these libertines of the effects box can also craft songs full of memorable hooks and melodies." Sub Pop asked Jessamine to record a single for their label, Drunken Fish asked them to contribute to the Harmony of the Spheres compilation alongside Flying Saucer Attack, Bardo Pond, Charalambides, and others. With the drum position secured by Michael Faeth, the band began touring the United States.
Jessamine recorded their second album, Long Arm of Coincidence in their home studio. Touring had made the band airtight, honing their melodic material as it fed their musical ambition. kranky released the double LP/CD in 1996.
Jessamine began a nationwide tour with Bardo Pond, then pulled up stakes and moved from Seattle to Portland in late 1996. With more room for home recording equipment. A sixteen track recording set up came together. A number of singles came out (later collected on the band's own Histrionic label as the CD Another Fictionalized History) and the group collaborated with Sonic Boom's Spectrum band for a cover of The Silver Apples' "A Pox On You." A massive live collaboration between Jessamine and Experimental Audio Research would later be released on Histrionic as well.
Then, in 1998, came the third album, Don't Stay Too Long. The band had tightened up on the extended interplay of previous recordings, concentrating on song structures.
Chris Wodskou wrote in Exclaim! that
At the point when so many musicians supposedly advancing the soundform were content to lean on the effects peddles, noodle away or dabble with breakbeats, Jessamine had crafted their best album, demonstrating how instrumental aptitude and sonic experimentation could be focussed into songs. For better or for worse, the band quit while they were on top. Dawn Smithson returned to college in Seattle and Michael Faeth moved to Davis, CA while Rex Ritter and Andy Brown completed their new studio Magnetic Park and began putting together Fontanelle.