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 | The Chipmunk Song | Chipmunks with David Seville |
| January 10 | ||
| January 17 | Smoke Gets In Your Eyes | The Platters |
| January 24 | ||
| January 31 | ||
| February 7 | ||
| February 14 | Stagger Lee | Lloyd Price |
| February 21 | ||
| February 28 | ||
| March 7 | Venus | Frankie Avalon |
| March 14 | ||
| March 21 | ||
| March 28 | ||
| April 4 | ||
| April 11 | Come Softly To Me | The Fleetwoods |
| April 18 | ||
| April 25 | ||
| May 2 | ||
| May 9 | The Happy Organ | Dave "Baby" Cortez |
| May 16 | ||
| May 23 | Kansas City | Wilbert Harrison |
| May 30 | The Battle of New Orleans | Johnny Horton |
| June 6 | ||
| June 13 | ||
| June 20 | ||
| June 27 | ||
| July 4 | ||
| July 11 | ||
| July 18 | ||
| July 25 | ||
| August 1 | Lonely Boy | Paul Anka |
| August 8 | ||
| August 15 | There Goes My Baby | The Drifters |
| August 22 | ||
| August 29 | The Three Bells | The Browns |
| September 5 | ||
| September 12 | ||
| September 19 | ||
| September 26 | Mack the Knife † | Bobby Darin |
| October 3 | ||
| October 10 | ||
| October 17 | ||
| October 24 | ||
| October 31 | ||
| November 7 | ||
| November 14 | Mr. Blue | The Fleetwoods |
| November 21 | Don't You Know? | 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 | Heartaches By The Number | Guy Mitchell |
| December 26 |