| | Song Title | Artist | CD Link | Track |
| | Please Mr. Postman | Marvelettes | 35 | 8 |
| | Please Please Me | Beatles | 20 | 12 |
| | Policeman's Lot is Not a Happy | Gilbert & Sullivan | 72 | 16 |
| | Poncho and Lefty | Willie Nelson | 25 | 11 |
| | Poor Wandering One | Gilbert & Sullivan | 72 | 14 |
| | Poor, Poor Pitiful Me | Terri Clark | 61 | 13 |
| | Pop | Nsync | 80 | 4 |
| | Pop a Top | Alan Jackson | 66 | 16 |
| | Pop Me Up Beside the Jukebox | Joe Diffie | 33 | 7 |
| | Positively 4th Street | Bob Dylan | 71 | 5 |
| | Pour Me | Trick Pony | 67 | 4 |
| | Precious Memories | Gospel | 6 | 2 |
| | Prisoner of the Highway | Ronnie Milsap | 18 | 9 |
| | Proud Mary | Creedence Clearwater Revival | 36 | 14 |
| | Pure Love | Ronnie Milsap | 17 | 1 |
| | Push It | Salt N Pepa | 81 | 6 |
| | Put You in a Song | Keith Urban | 88 | 7 |
| | Quando, Quando, Quando | Michael Buble | 31 | 6 |
| | Rag Doll | Four Seasons | 84 | 14 |
| | Rainy Day People | Gordon Lightfoot | 53 | 3 |
| | Rainy Day Women #12 & 35 | Bob Dylan | 71 | 6 |
| | Ramblin' Man | Allman Brothers | 36 | 11 |
| | Ramblin' Rose | Nat King Cole | 65 | 4 |
| | Rapid Roy (the Stock Car Boy) | Jim Croce | 53 | 8 |
| | Rapper's Delight | Sugar Hill Gang | 78 | 7 |
| | Rave On | Buddy Holly | 9 | 11 |
| | Raymond | Brett Eldridge | 90 | 7 |
| | Ready to Run | Dixie Chicks | 66 | 5 |
| | Red Red Wine | UB40 | 42 | 8 |
| | Red River Valley | Folk | 4 | 4 |
| | Refried Dreams | Tim McGraw | 33 | 5 |
| | Release Me | Ray Price | 63 | 7 |
| | Respect | Aretha Franklin | 59 | 7 |
| | Return to Sender | Elvis Presley | 69 | 20 |
| | Rhinestone Cowboy | Glen Campbell | 15 | 11 |
| | Right or Wrong | George Strait | 48 | 19 |
| | Ring of Fire | Johnny Cash | 65 | 1 |
| | River, The | Garth Brooks | 55 | 11 |
| | Rock and Roll Music | Chuck Berry | 11 | 11 |
| | Rock Around the Clock | Bill Haley & The Comets | 59 | 1 |
| | Rock My World | Brooks & Dunn | 33 | 10 |
| | Rock of Ages | Gospel | 6 | 8 |
| | Rock Show | Blink 182 | 77 | 15 |
| | Page 17 |