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

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.

@wsrrsw

I think you mean "Swiss Movement" , no?

@fthompson251 

Good! ;-)  Now try Ben Webster at the Renaissance.  Another great live recording, captured on an improvised early stereo setup by Webster's record producer.

There have been some excellent comments about the nature of jazz and what to listen for.  I'm a somewhat conservative fan.  I like it when I can:

1) Recognize the tune, or at least the chord changes, which are typically based on a standard tune, like "I Got Rhythm" or "How High the Moon" or something like that.   Certain sets of "changes" can be inspiring for the soloist and allow him or her to create interesting and memorable improvisations.

2) Tap my foot!  Whether it's a ballad or an up-tempo number, the rhythm section really has to swing.  I'm not knocking other approaches to jazz, but I do like to be moved to dance around the room a bit. ;-)  It's worth bearing in mind that many, many fine jazz albums of the '50's and '60's were geared toward people having cocktails and dancing in their homes.  It was hard to sell a record you couldn't dance to!