| Position | Title | Main Artist | Main Genre | Release Date | Up Vote(s) | Down Vote(s) | |
|---|---|---|---|---|---|---|---|
| 1 | An Apple for the Teacher | Bing Crosby | Jazz | 1992-01-01 | |||
| 2 | In My Merry Oldsmobile | Bing Crosby | Jazz | 1962-01-01 | |||
| 3 | A Man and His Dream | Bing Crosby | Jazz | 1992-01-01 | |||
| 4 | Gus Edwards Medley of Song Hits | Bing Crosby | classic pop | 1962-01-01 | |||
| 5 | Still the Bluebird Sings | Bing Crosby | Jazz | 1992-01-01 | |||
| 6 | Go Fly A Kite | Bing Crosby | Jazz | 1992-01-01 | |||
| 7 | If I Had My Way | Bing Crosby | Jazz | 1992-01-01 | |||
| 8 | Too Romantic | Bing Crosby | Jazz | 1992-01-01 | |||
| 9 | Sweet Potato Piper | Bing Crosby | Jazz | 1995-01-01 | |||
| 10 | April Played The Fiddle | Bing Crosby | Jazz | 1995-01-01 | |||
| 11 | The Moon and the Willow Tree | Bing Crosby | classic pop | 1962-01-01 | |||
| 12 | I Haven't Time to Be a Millionaire | Bing Crosby | Jazz | 1992-01-01 | |||
| 13 | Meet the Sun Half-Way | Bing Crosby | Jazz | 1992-01-01 | |||
| 14 | Pessimistic Character (With the Crab-Apple Face) | Bing Crosby | Jazz | 1999-01-01 |