These are the songs that reached number one on the Top 100 Best Sellers chart in 1959 as published by Cash Box magazine.
| Indicates best-performing single of 1959 |
| Issue date | Song | Artist | |
|---|---|---|---|
| January 3 | Chipmunks with David Seville | ||
| January 10 | |||
| January 17 | |||
| January 24 | |||
| January 31 | |||
| February 7 | |||
| February 14 | |||
| February 21 | |||
| February 28 | |||
| March 7 | Frankie Avalon | ||
| March 14 | |||
| March 21 | |||
| March 28 | |||
| April 4 | |||
| April 11 | |||
| April 18 | |||
| April 25 | |||
| May 2 | |||
| May 9 | Dave "Baby" Cortez | ||
| May 16 | |||
| May 23 | |||
| May 30 | Johnny Horton | ||
| June 6 | |||
| June 13 | |||
| June 20 | |||
| June 27 | |||
| July 4 | |||
| July 11 | |||
| July 18 | |||
| July 25 | |||
| August 1 | |||
| August 8 | |||
| August 15 | The Drifters | ||
| August 22 | |||
| August 29 | The Browns | ||
| September 5 | |||
| September 12 | |||
| September 19 | |||
| September 26 | bgcolor=#FFFF99 rowspan="7" | Bobby Darin | |
| October 3 | |||
| October 10 | |||
| October 17 | |||
| October 24 | |||
| October 31 | |||
| November 7 | |||
| November 14 | The Fleetwoods | ||
| November 21 | Della Reese | ||
| November 28 | Mr. Blue | The Fleetwoods | |
| December 5 | Don't You Know | Della Reese | |
| December 12 | Mack the Knife | Bobby Darin | |
| December 19 | Guy Mitchell | ||
| December 26 |