I'm not really ashamed of anything I listen to.
I listen mostly to country music, but none of that travis tritt/toby keith shit. that's just pop music, ya might as well be listening to Brittany Spears...
some bands i love:
Lucinda Williams
Johnny Cash
Hank Williams
Whiskeytown
Okkervil River
Puerto Muerto
Old 97's
Sixteen Horsepower
...there's really a sick country "underground" out there
One of the trendy-er things i listen to is Ryan Adams. His new album is great. total Hank Williams style

I guess the one singer I'm ashamed to admit loving is Pat Boone. I saw him a few years ago, at a high school in RI. His opening act was the local mentally retarded chorus!
one of the greatest things i've ever seen in my life...