"American Legend" Contest

I've been driving around with the same CD playing in the car for at least 3 weeks. The CD is from an American Legends series. I greatly admire this artist, while Sandra is extremely annoyed by them and opts for the radio when she is riding with me.

Who is the artist?


Who is this American legend?

It is not Tom T. Hall, Willie Nelson, Johnny Cash, or Roy Orbison.

The person who can identify this American Legend in 3 guesses or less will win a t-shirt from Ross Dress for Less.

I am going to work, please enter your guesses in the comments.
I will review your answers early this evening.
First person to guess correctly in 3 or fewer guesses wins.

If nobody guesses correctly, I will answer 3 questions about the American Legend and then all contestants will have 3 more guesses.

After my workout at the gym tonight, I will stop by Ross Dress for Less and choose a t-shirt.

Good luck and no cheating.