| 1 | Together | Frank Sinatra, Bing Crosby & Dean Martin | 3:44 |
| 2 | I’ll Never Smile Again | Frank Sinatra & The Hi‐Lo’s | 2:10 |
| 3 | Can’t We Be Friends | Frank Sinatra & Ella Fitzgerald | 3:04 |
| 4 | Medley: You Make Me Feel So Young / Them There Eyes / A Foggy Day / I’ve Got You Under My Skin / Taking a Chance on Love / They Can’t Take That Away From Me / All of Me / Daddy / I Can’t Give You Anything but Love / You Must Have Been a Beautiful Baby | Frank Sinatra & Dinah Shore | 5:50 |
| 5 | Nice Work If You Can Get It | Frank Sinatra & Peggy Lee | 2:31 |
| 6 | Side by Side | Frank Sinatra & Nancy Sinatra | 2:14 |
| 7 | Something’s Gotta Give | Frank Sinatra & The McGuire Sisters | 2:16 |
| 8 | High Hopes | Frank Sinatra and kids | 2:43 |
| 9 | If I Loved You | Frank Sinatra & Shirley Jones | 3:26 |
| 10 | Birth of the Blues | Frank Sinatra & Louis Armstrong | 3:23 |
| 11 | Medley: Sunday, Monday or Always / On a Slow Boat to China / Saturday Night Is the Loneliest Night of the Week / Memories Are Made of This / The Girl That I Marry / Innamorata / I’ve Got a Crush on You / Oh, Marie / Don’t Cry, Joe | Frank Sinatra & Dean Martin | 4:49 |
| 12 | Me and My Shadow | Frank Sinatra & Sammy Davis Jr. | 2:38 |
| 13 | September Song | Frank Sinatra & Bing Crosby | 1:57 |
| 14 | You’re the Top | Frank Sinatra & Ethel Merman | 1:39 |
| 15 | I Can’t Believe That You’re in Love With Me | Frank Sinatra, Louis Prima & Keely Smith | 1:05 |
| 16 | Harold Arlen (medley) | Frank Sinatra & Lena Horne | 3:59 |
| 17 | You Make Me Feel So Young | Frank Sinatra & Nancy Sinatra | 1:55 |
| 18 | Witchcraft / Love Me Tender | Frank Sinatra & Elvis Presley | 2:15 |
| 19 | Our Love Is Here to Stay | Frank Sinatra & Peggy Lee | 2:22 |
| 20 | Moonlight in Vermont / I May Be Wrong | Frank Sinatra & Ella Fitzgerald | 4:33 |
| 21 | Put Your Dreams Away | Frank Sinatra & Ella Fitzgerald | 0:47 |