Can you recommend Jazz for some one that doesn't like Jazz?

I'm in the same boat. Most jazz is just too busy and complex for me to enjoy. I like jazz ballads best. Simple and soulful music is my thing. 

Like you, I found Bill Frissell and Pat Matheny to be the most listenable. While both do their share of "complex" stuff, much of their work is more accessible to me. Stanley Turrentine has an album of ballads I like a lot. 

Bottom line for me is "do I feel it". Most jazz feels emotionless to me. It's music for musicians. 

Crusaders - Chain Reaction" LP is hard not to like.

I think that a big reason for the popularity of "jazz fusion" was because it felt somewhat familiar to rock music fans, yet it also represented a new avenue to explore. So, if "familiarity" is what you're looking for than your mention of Holly Cole might be important, since she tends to cover some well known songs that you are probably already familiar with.

If jazz vocalists are a priority, I'd add Michael Franks to your list.

@ fthompson251

Welcome to the Club!

I have tried to like Jazz for decades, as well, including a dozen deliberate weeks of "maybe this time", "maybe this group".  During the journey, I have found a few very good performers, but mostly duds.  Listening to 'giants' (Monk, Coltrane, Davis, etc.) was, mostly, painful.  I wish I could have these hours back...

With that perspective - I have some recommendations of Jazz performances that I truly enjoy and may be unique.

Getz/Jocbin

Boots Randolf

Henry James

Lenny Marcus - great Jazz transcriptions of Beethoven, plus some new pieces

Benny Goodman

Tommy & Jimmy Dorsey

Most of the Windham Hill artists - Montreux, Barbra Higbe, Daryl Anger, Michael Manring, Alex de Grassi, some Shadowfax, etc.

LA4

As someone suggested I listened to "Jazz at the Pawnshop" on Qubuz by Aren Domnerus. I made it through! 

There is an overwhelming about of infor mation on the thread, I can refer back ot it but this is a lot. Thanks to everyone. I've added about 15-20 songs to my Jazz playlist so far. What I do is use the qubuz web player keeping the window open and go through the suggestions on here from another window, then add those I like to the playlist after I listen. I use headphone fo that. All this takes time.