Great American Songbook & The Greatest Generation

I might not have spotted Brack's mention of the new Yes album, but I do know there are many forum residents whose parents were of the "Greatest Generation".  And that goes for both sides of the pond.  Today's been a veg-out type day devoted to putting together a disc for a doctor friend.  I got side-tracked with ZZ Top (thanks to Rocket), but the rest has been coming up with a Great American Songbook disc that the Doc loves.  I have to admit I do too since this music was playing all the time throughout my childhood.  Yesterday I put together an entire disc of Frank since he practically wrote the songbook himself.  That was fairly easy.  It's the second disc though that being both a chore and labor of love has morphed into an emotional rollercoaster.
I had almost forgotten adding Streisand since she didn't delve too deep into the "songbook", but the lady was huge back in the day and I included her song "People" for the list.  Looking at her catalog of music I remembered all those album covers strewn next to the family's Hi Fi and felt a stab of loss for the person responsible for the clutter.  My Mother.  My Mom absolutely adored Barbra, but she said on more than one occasion that Sinatra was her musicman.  She's the one that kindled my love for music.  Well I put together most of the playlist till I realized there wasn't any Tony Bennett.  I checked my library and there wasn't a single TB song in there.  Gotta say I was a bit shocked about this since I have in my possession what's left of her music on cd and thought I'd ripped everything into my computer.  When I pulled out her stuff I found three Tony Bennett cds that I hadn't touched.  When I opened up the case for the Ultimate Tony Bennett album I discovered a disc with fingerprints and crud all over it.  It cleaned up better than I thought and downloaded perfectly and when I started listening I found out why it was in the shape it was in.  Nurses, both at home and later at the nursing home had played this disc repeatedly for her.  It was difficult, but I remembered when she was slipping away that she still remembered all the words to these songs.  When I listened to the album I realized that it's Tony Bennett that's the epitome of singers of the songbook.  Sinatra himself conceded the pop crown to Tony and I definitely now agree.
I'd be curious what others think about this music and later I'll post my playlist for those that want to know what I came up with.