I'm a huge fan of Melissa Etheridge. I'm pretty sure I have everything she has ever done on both vinyl and CD. I really like her earlier stuff better.
My favorite albums are:
Melissa Etheridge
Brave and Crazy
Never Enough
Yes I Am
You could just start with "Greatest Hits: The Road Less Traveled" and go from there.
Can't really help you with Dean Martin, although I did just get the new MOFI LP release of "This Time I'm Swingin" and it is really good.