I've tried to put these in chronological order.

Puberty to Parenthood:

Last Time - Rolling Stones
A Day in the Life - Beatles
Purple Haze - Jimi Hendrix
White Room - Cream
Fried Hockey Boogie - Canned Heat
Dazed and Confused - Led Zeppelin
Whipping Post - Allman Brothers Band
I Know You Rider - Grateful Dead
Take it Easy / Our Lady of the Well - Jackson Brown
Will the Circle be Unbroken (the whole album) - NGDB

Parenthood to Present:

Ginseng Sullivan - Norman Blake
Old Fashioned Love - John Fahey
Bully of the Town - Highwoods Stringband
Hello in There - John Prine
Another Auld Lang Syne - Dan Fogelberg
Christmas in the Trenches - John McCutcheon
Fisherman's Blues - Waterboys
1952 Vincent Black Lightning - Richard Thompson
Drop Down Mamma - North Mississippi Allstars
Land's End - String Cheese Incident

Bruce