1. Stardust. I try to play this on the ukulele, and my voice always cracks when I get to the bit about “The nightingale tells his fairy tale, of Paradise where roses bloom.” But, truth be told, this song made me weep before I even heard the lyrics (and there were several hit records made of the tune before words were even penned for it, by Mitchell Parish). The solo piano recording of “Stardust” by its composer Hoagy Carmichael is one of the most beautiful records ever made.
2. This Guy’s in Love With You. I’m a child of the ‘60s, so this song (and Herb Alpert) have always been a part of my life. There was a little train-car diner in Northampton which had this on the jukebox for decades, just proving its timelessness. The barely sung, understated vocal here is a masterstroke of soft-pop production, contrasting with the trumpet blasts the way a later Bacharach/David cover, “Close to You,” would set Karen Carpenter against a booming angelic synth-choir. Due to the fact that you don’t need a strong voice to sing it, “This Guy” is one of the few Burt Bacharach tunes which Burt Bacharach himself can pull off as a concert vocalist; his recorded version is darn good, though of course no rendition can compete with Alpert’s.
3. Mr. Bojangles. A man who has nothing left mourns the dearest friend he ever had. I always start bawling when that line about the dog up-and-dying comes along. Doesn’t matter who’s singing—Sammy Davis Jr., Jim Stafford, the cast of Bob Fosse’s Dancin’…
4. Marie. From the finest concept album ever made, Randy Newman’s Good Old Boys. It’s a song of regret and vulnerability and and great, great love. Newman’s voice wobbles dramatically when he repeats “I loved you the first time I saw you/And I always will love you Marie,” showing how hard it is for his self-admittingly weak, lazy and hurtful narrator to say the words he needs to say.
5. When She Loved Me. Randy Newman again. I think there’s something in the chords he chooses that sets my tears flowing on so many of his songs, but his lyrics—which nail the fragility of affection—surely help. This is the song Sarah McLachlan sings to illustrate how a young girl in Toy Story 2 grows up and forsakes her former favorite toy, the cowgirl Jessie.