| 1 | If I Knew You Were Comin I’d Have Baked a Cake | Bing Crosby & Bob Hope | 2:50 |
| 2 | On a Slow Boat to China | Bing Crosby & Peggy Lee | 2:13 |
| 3 | When You Wore a Tulip and I Wore a Big Red Rose | Bing Crosby & Judy Garland | 2:59 |
| 4 | Till We Meet Again / Meet Me Tonight in Dreamland / There’s a Long Long Trail | Bing Crosby & Frank Sinatra | 4:39 |
| 5 | Moonlight Bay | Bing Crosby & Gary Crosby | 3:18 |
| 6 | I Don’t Know Why (I Just Do) | Bing Crosby & Lauren Bacall | 2:20 |
| 7 | The One I Love Belongs to Somebody Else | Bing Crosby & Al Jolson | 1:56 |
| 8 | May the Good Lord Bless and Keep You | Bing Crosby, Nat King Cole & The Andrews Sisters | 3:17 |
| 9 | It Could Happen to You / I Heard You Cry Last Night / I’ll Get By / I Don’t Believe It / Out of Nowhere / Going My Way / Sunday, Monday or Always | Bing Crosby & Frank Sinatra | 2:19 |
| 10 | Basin Street Blues | Bing Crosby & Ella Fitzgerald | 2:58 |
| 11 | Hand Holdin’ Music | Bing Crosby, Rudy Vallée & Walter O’Keefe | 3:25 |
| 12 | (Up A) Lazy River / Paper Doll | Bing Crosby & The Mills Brothers | 3:28 |
| 13 | On Top of Old Smokey | Bing Crosby & Burl Ives | 3:07 |
| 14 | You Are My Sunshine / Sonny Boy / You’re the Top | Bing Crosby, Frank Sinatra & Bob Hope | 3:05 |
| 15 | Clancy Lowered the Boom | Bing Crosby & Dennis Day | 3:27 |
| 16 | Takes Two to Tango | Bing Crosby & Rosemary Clooney | 2:34 |
| 17 | You Came a Long Way from St. Louis | Bing Crosby & Peggy Lee | 2:38 |
| 18 | I Can Dream Can’t I | Bing Crosby & The Andrews Sisters | 3:01 |
| 19 | Among My Souvenirs / September Song / As Time Goes By | Bing Crosby & Frank Sinatra | 6:20 |
| 20 | Lullaby of Broadway | Bing Crosby & Dick Powell | 1:45 |
| 21 | The Surrey With the Fringe On Top | Bing Crosby & Helen O’Connell | 2:48 |
| 22 | Till We Meet Again | Bing Crosby & Patti Page | 2:30 |
| 23 | Groaner, Canary and Nose | Bing Crosby, Judy Garland & Jimmy Durante | 3:02 |
| 24 | The Christmas Song | Bing Crosby & Frank Sinatra | 1:40 |