| 1 | Jolene | Dolly Parton | | 4.25 | 2:41 |
| 2 | I Walk the Line | Johnny Cash | | | 2:56 |
| 3 | Crazy | Patsy Cline | | 4.15 | 2:44 |
| 4 | I’m So Lonesome I Could Cry | Hank Williams with His Drifting Cowboys | | 4.25 | 2:48 |
| 5 | He Stopped Loving Her Today | George Jones | | | ?:?? |
| 6 | You Don’t Know Me | Ray Charles | | | 3:16 |
| 7 | Blue Yodel No. 9 (Standin’ on the Corner) | Jimmie Rodgers & Louis Armstrong | | 3 | 2:40 |
| 8 | Stand by Your Man | Tammy Wynette | | 4 | 2:41 |
| 9 | Mama Tried | Merle Haggard | | 5 | 2:11 |
| 10 | Amarillo by Morning | George Strait | | 5 | 2:53 |
| 11 | It Wasn’t God Who Made Honky Tonk Angels | Kitty Wells | | | ?:?? |
| 12 | Wichita Lineman | Glen Campbell | | 3.65 | 3:05 |
| 13 | New San Antonio Rose | Bob Wills and His Texas Playboys | | | 2:48 |
| 14 | Coal Miner’s Daughter | Loretta Lynn | | 4 | 3:01 |
| 15 | Can the Circle Be Unbroken (Bye and Bye) | The Carter Family | | | 3:08 |
| 16 | I’ve Got a Tiger by the Tail | Buck Owens | | | 2:14 |
| 17 | Walking the Floor Over You | Ernest Tubb | | | 2:05 |
| 18 | If You’ve Got the Money I’ve Got the Time | Lefty Frizzell | | | 2:57 |
| 19 | Kiss an Angel Good Mornin’ | Charley Pride | | 4.5 | 2:04 |
| 20 | Mean | Taylor Swift | | 4 | 3:58 |
| 21 | The Gambler | Kenny Rogers | | 4.5 | 3:32 |
| 22 | Man of Constant Sorrow | The Stanley Brothers | | | 2:57 |
| 23 | Goodbye Earl | Dixie Chicks | | 4.5 | 4:20 |
| 24 | Behind Closed Doors | Charlie Rich | | | ?:?? |
| 25 | Ring of Fire | Johnny Cash | | 4.25 | 2:37 |
| 26 | Hello Walls | Faron Young | | | 3:24 |
| 27 | Blue Eyes Crying in the Rain | Willie Nelson | | 4 | 2:21 |
| 28 | Your Cheatin’ Heart | Hank Williams | | 4 | 2:43 |
| 29 | Sitting on Top of the World, No. 2 | Mississippi Sheiks | | | 3:20 |
| 30 | Man! I Feel Like a Woman! | Shania Twain | | 3 | 3:53 |
| 31 | A Satisfied Mind | Porter Wagoner | | | 2:43 |
| 32 | Wildwood Flower | The Carter Family | | 4 | 3:12 |
| 33 | Bye Bye Love | The Everly Brothers | | 4.35 | 2:22 |
| 34 | Are You Sure Hank Done It This Way | Waylon Jennings | | | 2:53 |
| 35 | Friends in Low Places | Garth Brooks | | 4.6 | 4:19 |
| 36 | Follow Your Arrow | Kacey Musgraves | | 3.5 | 3:20 |
| 37 | Pancho and Lefty | Townes van Zandt | | | 3:41 |
| 38 | Don’t Come Home a Drinkin’ (With Lovin’ on Your Mind) | Loretta Lynn | | 4 | 2:09 |
| 39 | She’s Actin’ Single (I’m Drinkin’ Doubles) | Gary Stewart | | 5 | 2:49 |
| 40 | The Grand Tour | George Jones | | 4 | 3:08 |
| 41 | Neon Moon | Brooks & Dunn | | 4.5 | 4:22 |
| 42 | Blue Yodel (T for Texas) | Jimmie Rodgers | | 3.5 | 3:25 |
| 43 | Lost Highway | Hank Williams | | | 2:09 |
| 44 | I Wanna Be a Cowboy’s Sweetheart | Patsy Montana | | | 3:08 |
| 45 | Independence Day | Martina McBride | | 4.65 | 3:25 |
| 46 | Coat of Many Colors | Dolly Parton | | 4 | 3:05 |
| 47 | Before the Next Teardrop Falls | Freddy Fender | | | 2:16 |
| 48 | Forever and Ever, Amen | Randy Travis | | 4.65 | 3:33 |
| 49 | Blue Moon of Kentucky | Elvis Presley | | 3.5 | 2:05 |
| 50 | Old Dogs, Children and Watermelon Wine | Tom T. Hall | | | 4:12 |
| 51 | Ode to Billie Joe | Bobbie Gentry | | 5 | 4:15 |
| 52 | Drive (for Daddy Gene) | Alan Jackson | | 4.5 | 4:03 |
| 53 | Wabash Cannonball | Roy Acuff | | 3 | 2:36 |
| 54 | Folsom Prison Blues | Johnny Cash | | 4.85 | 2:44 |
| 55 | I Saw the Light | Hank Williams, Jr. | | | 2:45 |
| 56 | Take This Job and Shove It | Johnny Paycheck | | | 2:39 |
| 57 | Foggy Mountain Breakdown | Lester Flatt & Earl Scruggs | | | 2:21 |
| 58 | Springsteen | Eric Church | | 4 | 4:23 |
| 59 | D‐I‐V‐O‐R‐C‐E | Tammy Wynette | | 4 | 2:57 |
| 60 | King of the Road | Billy Strange | | | 2:32 |
| 61 | Mountain Music | Alabama | | | ?:?? |
| 62 | The Long Black Veil | Lefty Frizzell | | 4 | 3:05 |
| 63 | Golden Ring | George Jones & Tammy Wynette | | | 3:02 |
| 64 | Uncle Pen | Bill Monroe and the Bluegrass Boys | | | ?:?? |
| 65 | Fancy | Reba | | 3.5 | 4:58 |
| 66 | El Paso | Marty Robbins | | 5 | 4:23 |
| 67 | Before He Cheats | Carrie Underwood | | 3.9 | 3:20 |
| 68 | Delta Dawn | Tanya Tucker | | | 4:14 |
| 69 | Mammas Don’t Let Your Babies Grow up to Be Cowboys | Waylon Jennings & Willie Nelson | | | 2:34 |
| 70 | Act Naturally | Buck Owens | | | 2:11 |
| 71 | Help Me Make It Through the Night | Sammi Smith | | | 2:25 |
| 72 | I Fall to Pieces | Patsy Cline | | 5 | 2:50 |
| 73 | Seven Year Ache | Rosanne Cash | | | 3:16 |
| 74 | Race Is On | George Jones | | | 2:05 |
| 75 | I Hope You Dance | Lee Ann Womack special guest appearance Sons of the Desert | | 4.65 | 4:55 |
| 76 | Songs About Rain | Gary Allan | | 5 | 3:54 |
| 77 | The House That Built Me | Miranda Lambert | | 3.65 | 3:57 |
| 78 | Harper Valley P.T.A. | Jeannie C. Riley | | 4 | 3:15 |
| 79 | Settin’ the Woods on Fire | Hank Williams | | | 2:38 |
| 80 | Girl Crush | Little Big Town | | 3.9 | 3:13 |
| 81 | Angel From Montgomery | John Prine | | 4.35 | 3:44 |
| 82 | Rocky Top | Brothers Osborne | | | 2:37 |
| 83 | Family Tradition | Hank Williams, Jr. | | | 4:04 |
| 84 | Why Not Me | The Judds | | 4.5 | 3:30 |
| 85 | Wild and Blue | John Anderson | | 5 | 2:48 |
| 86 | Color Him Father | Linda Martell | | | 2:41 |
| 87 | I Don’t Believe You’ve Met My Baby | The Louvin Brothers | | | 2:08 |
| 88 | Rose Garden | Lynn Anderson | | | 2:58 |
| 89 | Dallas | The Flatlanders | | 3 | 2:49 |
| 90 | Tennessee Whiskey | Chris Stapleton | | 4.35 | 4:53 |
| 91 | When I Call Your Name | Vince Gill | | 4 | 4:16 |
| 92 | Lovesick Blues | Emmett Miller | | | ?:?? |
| 93 | My Church | Maren Morris | | 3.4 | 3:17 |
| 94 | Take Me Home, Country Roads | John Denver | | 4.3 | 3:12 |
| 95 | What Made Milwaukee Famous (Has Made a Loser Out of Me) | Jerry Lee Lewis | | | 2:37 |
| 96 | Sunday Mornin’ Comin’ Down | Kris Kristofferson | | 3.5 | 4:32 |
| 97 | Happiest Girl in the Whole USA | Donna Fargo | | | 2:33 |
| 98 | I Love This Bar | Toby Keith | | 4.5 | 5:35 |
| 99 | Streets of Baltimore | Bobby Bare | | | 2:41 |
| 100 | Passionate Kisses | Lucinda Williams | | | 2:38 |
