| 1 | Angel Eyes | great arrangements |
| 2 | Begin the Beguine | mood-changing music |
| 3 | The Brooklyn Bridge | bridges |
| 4 | Come Fly With Me | flying |
| 5 | Fools Rush In | proverbs & idioms |
| 6 | High Hopes (with Eddie Hodges) | children performing |
| 7 | I Get a Kick Out of You | boredom |
| 8 | In the Wee Small Hours of the Morning | sleep & insomnia |
| 9 | It Was a Very Good Year | getting older |
| 10 | It Was a Very Good Year | old age |
| 11 | Just One of Those Things | impermanence |
| 12 | Me and My Shadow (with Sammy Davis Jr.) | empathy |
| 13 | One for My Baby (And One More for the Road) | pubs & bars |
| 14 | September Song | autumn |
| 15 | Strangers in the Night | flirting |
| 16 | Summer Wind | personification |
| 17 | That’s Life | starting over |
| 18 | Then Suddenly Love | firsts & lasts |
| 19 | They Can’t Take That Away from Me | upbeat break-up |
| 20 | You Make Me Feel So Young | joyous |
| 21 | Young at Heart | youthfulness |