Wonderful idea. There are so many songs that mark a place in time or a person for me.
For my son: Cats in the Cradle by Harry Chapin.
For my daughter: My girl by the Temptations, Love Me Tender by Elvis and Weave Me The Sunshine by Peter Paul and Mary (I used to sing these to her starting when she was a baby but probably until age 12 or something like that).
For my wife: The Joy That is You and Old Love by Neal and Leandra.
For both kids: For Baby (For Bobby) by John Denver. Forever Young by Bob Dylan (but I like Joan Baez’s version better).
Sophomore/Junior Year: Lay Lady Lay and a bunch of Bob Dylan. Crosby Stills and Nash (Suite Judy Blue Eyes) and others), Neil Young (Heart of Gold), Gordon Lightfoot (Early Mornin Rain)
Senior Year: Crazy Love by Van Morrison.
First Year of Grad School: Linda Ronstadt: Long, Long Time, Faithless Love, Willin’, When Will I Be Loved, …
Second Year of Grad School: Elvis Costello (Angels Want to Wear My Red Shoes, Oliver’s Army, Alison, …), Steve Forbert (Romeo’s Tune, Complications).
Please Come to Boston by Dave Loggins.
Danny’s Song by Loggins and Messina.
My Happy Song: Dancing in the Moonlight by Harvest. A few Beach Boys Songs:
More recent:
Angelina Jordan sings in a way that is somehow very moving: Summertime (when she was 8), Bohemian Rhapsody, Suspicious Minds, Always on My Mind. She is a star about to happen. She’s mostly on YouTube.
Janileigh Cohen: Blues Run The Game, Long Black Veil. She’s mostly on Youtube as well.
Leonard Cohen: Bird on The Wire, Hallelujah, Suzanne, Dance Me to the End of Love.
Billie Eilish: Ocean Eyes.
Toussaint McCall: Nothing Takes the Place of You.
Etta James At Last.
Janis Ian Seventeen.