| 1 | The Lady Is a Tramp | ♡ | 3:25 | Richard Rodgers / Lorenz Hart / Billy Byers | Frank Sinatra / Luther Vandross |
| 2 | What Now, My Love? | ♡ | 3:15 | Pierre Delanoë / Gilbert Bécaud / Patrick Williams / Don Costa | Frank Sinatra / Aretha Franklin |
| 3 | I’ve Got a Crush on You | ♡ | 3:24 | Ira Gershwin / George Gershwin / Patrick Williams | Frank Sinatra / Barbra Streisand |
| 4 | Summer Wind | ♡ | 2:33 | Johnny Mercer / Henry Mayer / Nelson Riddle | Frank Sinatra / Julio Iglesias |
| 5 | Come Rain or Come Shine | ♡ | 4:04 | Harold Arlen / Johnny Mercer / Don Costa | Frank Sinatra / Gloria Estefan |
| 6 | New York, New York | ♡ | 3:30 | John Kander / Fred Ebb / Don Costa | Frank Sinatra / Tony Bennett |
| 7 | They Can’t Take That Away from Me | ♡ | 3:11 | Ira Gershwin / George Gershwin / Patrick Williams | Frank Sinatra / Natalie Cole |
| 8 | You Make Me Feel so Young | ♡ | 3:06 | Josef Myrow / Mack Gordon / Quincy Jones | Frank Sinatra / Charles Aznavour |
| 9 | Guess I’ll Hang My Tears Out to Dry/In the Wee Small Hours of the … | ♡ | 3:57 | Nelson Riddle / Bob Hilliard / Sammy Cahn / David Mann / Jule Styne | Frank Sinatra / Carly Simon |
| 10 | I’ve Got the World on a String | ♡ | 2:19 | Harold Arlen / Ted Koehler / Nelson Riddle | Frank Sinatra / Liza Minnelli |
| 11 | Witchcraft | ♡ | 3:22 | Cy Coleman / Carolyn Leigh / Patrick Williams / Nelson Riddle | Frank Sinatra / Anita Baker |
| 12 | I’ve Got You Under My Skin | ♡ | 3:33 | Cole Porter / Nelson Riddle | Frank Sinatra / Bono |
| 13 | All the Way/One for My Baby (And One More for the Road) | ♡ | 6:04 | Patrick Williams / Nelson Riddle / Johnny Mercer / Sammy Cahn / Harold Arlen / Jimmy Van Heusen | Frank Sinatra / Kenny G |