Lists like this are typically hard to do, mostly because it is so subjective and there really isn’t any metrics to compare one person to the next.
My top five list could totally change from one day to the next.
Instead of making a top five list, I will just list some people that could be in my top five at any given moment, but I will exclude any artist that was previously mentioned.
Also, I purposely listed some artists that people may not think of, but imo, deserve to be mentioned.
Males, everyone has some great artists so far, my list has some that I think could top those already mentioned:
Andrea Bocelli – I am surprised he hasn’t been mentioned already.
Chris Cornell – Powerful voice, so recognizable.
Tom Jones – One of the greats.
Axl Rose – Probably not on most people’s radar, but worth considering. His vocal style is like a male version of Janis Joplin, imo.
George Michael – People tend to forget the amazing voice he had.
Johnny Cash – Wasn’t always a fan, but his vocals in “Hurt” gives me chills.
Frank Sinatra – Another one I was surprise didn’t get a mention.
Jeff Buckley – His version of Hallelujah is my favorite, so sad.
Elton John - So iconic, but so many younger people today can’t even name one of his songs…. Sad
Willie Nelson - Probably another one that gets forgotten about.
Females, I tend to like female artists with an angelic sounding voice, so my list might be biased that way, but I am surprised that a few hasn’t been mentioned so far:
Sarah Brightman – The most angelic voice, so beautiful. I don't think she was on the Rolling Stone top 100 either, not sure how she was missed.
Celine Dion - How was she not mentioned so far?
Sarah McLachlan - Her song “Angel” was perfectly sad long before it was about sad puppies.
Alison Krauss - Another angelic voice.
Alicia Keys - Not always a fan of modern R&B, but Alicia Keys has such a wonderful voice.
Lana Del Rey - She would probably be considered pop, but there is something "old" about her sound, and in a good way.
Sara Bareilles - Just listen to 'Gravity'.
LeAnn Rimes - I think she often gets forgotten about, maybe she isn’t for everyone, but I love her voice.
Sheryl Crow - Nice vocals, she does one of my favorite Bond songs.
Dolly Parton - Another one people forget about. Since most people’s list would probably include Whitney Houston (and justifiably so), and Houston’s version of “I will always love you” was arguably her most popular song, I personally think that Dolly’s version better captures the sadness of the lyrics. Which is a little ironic, considering Houston’s character in the movie ‘Body Guard’ makes a comment about how sad the lyrics of the song. Houston’s version just sounds too loud, imo. I wouldn’t rate Dolly above Houston overall, but it is interesting to see the difference in styles on a song that both sing.