Throughout the 1990s he was a fixture in the East Lansing indie-rock scene, alongside fellow local acts like The Verve Pipe.
While majoring in political science at Michigan State University's James Madison College,[1] he performed at various Lansing-area open mic nights, gaining significant local popularity.
His classic 1992 "Songs About Stuff" LP featured fan favorites like "Small Time Drug Dealer" and "Psycho Roommate."
Pleasant has performed throughout the United States over the years, especially in areas where large numbers of MSU Spartan alumni have settled.
Primarily a solo artist, Pleasant performed occasionally in the 1990s with individual sidemen (electric guitarists, bassists) and with a four-piece band, The Happy Neighborhood.