OK, I'll play. Easy to pick my number 1. 2-5 are in no particular order.
1. The Who (1980) -- We had tenth row center seats, and I just remember standing there as they started Baba O'Riley (third song) and grinning ear to ear.
2. Talking Heads (1982?) -- Tina Weymouth was pregnant and Tom Tom Club opened up for the Heads.
3. Supertramp (1979) -- 1979 One of my earliest concerts and though we had bad seats I couldn't believe how good they sounded.
4. Eagles -- Alpine Valley, WI. We had third row seats and Jackson Browne, who we had seen the night before in Chicago, came out to perform Take It Easy with them.
5. Todd Rundgren and Utopia -- I've seen Utopia 2 times and Todd solo thric, but my favorite concert was probably Utopia at Alpine Valley. Good seats, great weather, and an experienced Utopia crowd. The energy during songs like Love is the Answer and Just One Victory was amazing.
Stevie Wonder in the round at Assembly Hall in Champaign, IL.
Keb Mo at House of Blues in Chicago. Seen him 4 times, but the small venue and it being the first time made it the best.
Aretha Franklin, also at House of Blues. She had to take a fairly long break in the middle, but it was still great seeing this icon.
Girlfriend at the time bought tickets for a night with Windham Hill artists. Wasn't exactly the most invigorating concert, and then Michael Hedges cam on stage with just his guitar. Incredible.