In no particular order:

1. Tony Bennett
2. Joe Williams (deceased)
3. George Jones (deceased)
4. K D Lang

What? No Sinatra?

Frank Sinatra, in my opinion, is a "big room" entertainer. These four can work a "small room" (aka: "saloon") with the best of them.

To Tony Bennett and KD Lang I would add Diana Krall and Linda Ronstadt.
Wait . . . Maybe scratch Diana Krall and add Taj Mahal.

To Tony Bennett and KD Lang I would add Diana Krall and Linda Ronstadt.
Wait . . . Maybe scratch Diana Krall and add Taj Mahal.

Don't be scratchin' Diana!!:Smiley122

Don't be scratchin' Diana!!:Smiley122
That thought crossed my mind right after I typed it, but I chose not to edit the post. =)
(I've mentioned this before, but I actually saw Taj Mahal and Linda Ronstadt in a saloon,
a small room called Tulagi, and believe me: They could work it.)

I like Ken's list, but given a choice, I would swap Enya for K D Lang. I like Lang ok, but well, yeah, I liked Enya better back when I was prone to just spend an evening sipping, thinking and visiting.

Frank Sinatra and Linda Ronstadt have powerfully beautiful voices. I can't comment on Taj Mahal.

He would add variety and diversity to the mix. Sort of an homage to roots music and blues. Plus, the time I saw him he started the one-man show by playing the kalimba (Africa thumb piano). Truly an amazing artist and performer. No back-up band at all. Although, technically, I don't suppose he would be labeled a "saloon singer" . . . so put Ms. Krall back in the lineup.

(i might like to have Enya over for Samhain or Solstice entertainment. I'm not so sure about a New Year's Eve saloon. A small room might be too small to contain Oranoco Flow.)

... I can't comment on Taj Mahal.
Taj Mahal is cool for the blues.

all great!! could sit, sip, and listen to all of the above for way too many hours!!

I've always been a fan of Sammy Davis, Jr. Not because he was a
great Jazz singer, he wasn't, but because he was a major talent.

In other words, Sammy could sing, dance and act better than anyone.
Sammy was the consummate entertainer. He was the supreme Triple
Threat. Nobody could compare to Sammy. Frank and Dino were close,
but they didn't get the cigar.

At the top of this thread, I immediately thought of Diana Krall. And how about Ruth Brown and Sophie Milman?