| 1 | The Lady Is a Tramp | Frank Sinatra with Luther Vandross | 3:24 |
| 2 | What Now, My Love? | Frank Sinatra with Aretha Franklin | 3:15 |
| 3 | I’ve Got a Crush on You | Frank Sinatra with Barbra Streisand | 3:23 |
| 4 | Summer Wind | Frank Sinatra with Julio Iglesias | 2:32 |
| 5 | Come Rain or Come Shine | Frank Sinatra with Gloria Estefan | 4:04 |
| 6 | New York, New York | Frank Sinatra with Tony Bennett | 3:30 |
| 7 | They Can’t Take That Away From Me | Frank Sinatra with Natalie Cole | 3:11 |
| 8 | You Make Me Feel So Young | Frank Sinatra with Charles Aznavour | 3:05 |
| 9 | Guess I’ll Hang My Tears Out to Dry / In the Wee Small Hours of the Morning | Frank Sinatra with Carly Simon | 3:57 |
| 10 | I’ve Got the World on a String | Frank Sinatra with Liza Minnelli | 2:18 |
| 11 | Witchcraft | Frank Sinatra with Anita Baker | 3:22 |
| 12 | I’ve Got You Under My Skin | Frank Sinatra with Bono | 3:32 |
| 13 | All the Way / One for My Baby (And One More for the Road) | Frank Sinatra with Kenny G | 6:03 |
| 1 | For Once in My Life | Frank Sinatra with Gladys Knight and Stevie Wonder | 3:18 |
| 2 | Come Fly With Me | Frank Sinatra with Luis Miguel | 3:08 |
| 3 | Bewitched | Frank Sinatra with Patti LaBelle | 3:31 |
| 4 | The Best Is Yet to Come | Frank Sinatra with Jon Secada | 3:13 |
| 5 | Moonlight in Vermont | Frank Sinatra with Linda Ronstadt | 4:07 |
| 6 | Fly Me to the Moon | Frank Sinatra with Antonio Carlos Jobim | 3:06 |
| 7 | Luck Be a Lady | Frank Sinatra with Chrissie Hynde | 5:17 |
| 8 | A Foggy Day | Frank Sinatra with Willie Nelson | 2:24 |
| 9 | Where or When | Frank Sinatra with Steve Lawrence and Eydie Gorme | 3:53 |
| 10 | Embraceable You | Frank Sinatra with Lena Horne | 3:45 |
| 11 | Mack the Knife | Frank Sinatra with Jimmy Buffett | 4:26 |
| 12 | How Do You Keep the Music Playing? / My Funny Valentine | Frank Sinatra with Lorrie Morgan | 3:58 |
| 13 | My Kind of Town | Frank Sinatra with Frank Sinatra Jr. | 2:36 |
| 14 | The House I Live In (That’s America to Me) | Frank Sinatra with Neil Diamond | 4:15 |
| 1 | Introduction | Frank Sinatra, Barbara Sinatra, Sid Mark & Tony Renaud | 6:33 |
| 2 | Come Rain or Come Shine (with commentary) | Frank Sinatra with Gloria Estefan | 5:52 |
| 3 | New York, New York (with Commentary) | Frank Sinatra with Tony Bennett | 7:25 |
| 4 | I’ve Got You Under My Skin (with commentary) | Frank Sinatra with Bono | 9:40 |
| 5 | What Now, My Love? (with Commentary) | Frank Sinatra with Aretha Franklin | 6:28 |
| 6 | Guess I’ll Hang My Tears Out to Dry / In the Wee Small Hours of the Morning (with commentary) | Frank Sinatra with Carly Simon | 4:51 |
| 7 | They Can’t Take That Away From Me (with commentary) | Frank Sinatra with Natalie Cole | 3:15 |
| 8 | The Best Is Yet to Come (with commentary) | Frank Sinatra with Jon Secada | 3:17 |
| 9 | A Foggy Day (with commentary) | Frank Sinatra with Willie Nelson | 2:50 |
| 10 | Where or When (with commentary) | Frank Sinatra with Steve Lawrence and Eydie Gorme | 7:01 |
| 11 | Embraceable You (with commentary) | Frank Sinatra with Lena Horne | 4:01 |
| 12 | My Kind of Town (with commentary) | Frank Sinatra with Frank Sinatra, Jr. | 5:14 |