Okay, if we're going for personal lists (this is gonna be tough):
1. Tom Zé -- Park West, Chicago 1998
2. Big Star -- Metro, Chicago 1994
3. Fishbone -- Jesse Hall, Columbia, MO 1989
4. Violent Femmes/The Pogues/Mojo Nixon -- Poplar Creek, Hoffman Estates, IL 1989
5. fIREHOSE/Uncle Tupelo -- The Blue Note, Columbia, MO 1989
6. Television -- Mississippi Nights, St. Louis 1992
7. Neutral Milk Hotel -- Lounge Ax, Chicago 1998
8. Super Furry Animals -- Lounge Ax, Chicago 1997
9. Jonathan Richman -- multiple times, multiple venues
10. Meat Puppets -- Metro, Chicago 1988

Honorable mentions:
Prince -- The Mark, Moline, IL 1998
Roger Waters -- World Music Theater, Tinley Park, IL 2009
Stereolab/Tortoise -- Lounge Ax, Chicago 1996
U2 -- Rosemont Horizon, Rosemont, IL 1987
Pixies -- The Blue Note, Columbia, MO 1989
The Pogues -- Riviera, Chicago 2009

Yeah, 1989 was a very good year for me and live music.