Penny, I used to carry my boombox around all the time too!
I love almost all kinds of music so I will just list my very top faves.
Hands down, Skynyrd is at the top! The rest are in no particular order.
Lynyrd Skynyrd (have seen at least 8 times)
Prince (never saw in concert
)
Corey Stevens (lost count of how many times we've seen him after we hit 50 times)
Kid Rock (I think I'm up to 5 times now)
Travis Tritt (I think 3 times)
Dwight Yoakam (I think twice)
Darius Rucker (still hoping to see him soon!)
There are so many others I love too!
ETA: How could I forget my still-beloved New Kids on the Block!?