| 1. Lonestar - Amazed | not rated | 4:05 |
| 2. Kenny Chesney - How Forever Feels | not rated | 3:10 |
| 3. George Strait - Write This Down | not rated | 3:39 |
| 4. Tim McGraw - Something Like That | not rated | 3:03 |
| 5. Jo Dee Messina - Lesson In Leavin' | not rated | 3:36 |
| 6. Tim McGraw - Please Remember Me | not rated | 4:55 |
| 7. Martina McBride - I Love You | not rated | 2:56 |
| 8. Billboard Top Country Singles Of 1999 - 008 - Jo Dee Messina - Stand Beside Me | not rated | 3:42 |
| 9. Kenny Chesney - You Had Me From Hello | not rated | 3:48 |
| 10. Mark Chesnutt - I Don't Want To Miss A Thing | not rated | 4:06 |
| 11. Dixie Chicks - You Were Mine | not rated | 3:36 |
| 12. Terri Clark - You're Easy On The Eyes | not rated | 3:33 |
| 13. Mark Wills - Wish You Were Here | not rated | 4:01 |
| 14. Billboard Top Country Singles Of 1999 - 014 - Chely Wright - Single White Female | not rated | 3:19 |
| 15. George Strait - What Do You Say To That | not rated | 3:00 |
| 16. Martina Mcbride - Wrong Again | not rated | 3:15 |
| 17. Diamond Rio - Unbelievable | not rated | 2:21 |
| 18. Billboard Top Country Singles Of 1999 - 018 - Steve Wariner - I'm Already Taken | not rated | 1:16 |
| 19. Sarah Evans - No Place That Far | not rated | 3:37 |
| 20. Ty Herndon - It Must Be Love | not rated | 3:32 |
| 21. Andy Grigg - You Won't Ever Be Lonely | not rated | 3:32 |
| 22. Martina Mcbride - Whatever You Say | not rated | 4:30 |
| 23. ALABAMA - God Must Have Spent A Little.. | not rated | 3:25 |
| 24. Billboard Top Country Singles Of 1999 - 024 - Alan Jackson - Right On The Money | not rated | 3:46 |
| 25. Billboard Top Country Singles Of 1999 - 025 - Shedaisy - Little Goodbyes | not rated | 3:22 |
| 26. Faith Hill - Let Me Let Go | not rated | 4:24 |
| 27. Joe Diffie - A Night to Remember | not rated | 3:34 |
| 28. Steve Wariner - Two Teardrops | not rated | 4:30 |
| 29. Billboard Top Country Singles Of 1999 - 029 - Montgomery Gentry - Lonely And Gone | not rated | 3:20 |
| 30. Brooks & Dunn - Husbands And Wives | not rated | 3:10 |
| 31. Billboard Top Country Singles Of 1999 - 031 - Dixie Chicks - Ready To Run | not rated | 3:51 |
| 32. Billboard Top Country Singles Of 1999 - 032 - Lee Ann Womack - I'll Think Of A Reason Later | not rated | 3:38 |
| 33. Billy Ray Cyrus - Busy Man | not rated | 3:17 |
| 34. Faith Hill - The Secret of Life | not rated | 4:14 |
| 35. Collin Raye - Someone You Used To Know | not rated | 2:34 |
| 36. Alan Jackson - Alan Jackson - Little Man | not rated | 4:29 |
| 37. John Michael Montgomery - Hold On To Me | not rated | 4:10 |
| 38. Clay Walker - You're Beginning To Get To Me | not rated | 2:41 |
| 39. BlackHawk - There You Have It | not rated | 3:12 |
| 40. Collin Raye - Anyone Else | not rated | 0:51 |
| 41. Billboard Top Country Singles Of 1999 - 041 - Alabama - Christmas In Dixie | not rated | 3:35 |
| 42. Billboard Top Country Singles Of 1999 - 042 - Aaron Tippin - For You I Will | not rated | 3:32 |
| 43. Andy Griggs - I'll Go Crazy | not rated | 3:04 |
| 44. Randy Travis - Spirit Of A Boy, Wisdom Of A M | not rated | 3:51 |
| 45. Chad Brock - Ordinary Life | not rated | 3:57 |
| 46. Billboard Top Country Singles Of 1999 - 046 - Alan Jackson - Gone Crazy | not rated | 3:50 |
| 47. Billboard Top Country Singles Of 1999 - 047 - Trisha Yearwood - I'll Still Love You More | not rated | 4:23 |
| 48. Lila McCann - With You | not rated | 3:31 |
| 49. Ty Herndon - Hands Of A Working Man | not rated | 3:47 |
| 50. Billboard Top Country Singles Of 1999 - 050 - Shania Twain - Man, I Feel Like A Woman | not rated | 3:53 |
| 51. Billboard Top Country Singles Of 1999 - 051 - John Michael Montgomery - Home To You | not rated | 3:29 |
| 52. Billboard Top Country Singles Of 1999 - 052 - Clint Black - When I Said I Do | not rated | 4:30 |
| 53. Dixie Chicks - Tonight The Heartache's On Me | not rated | 3:26 |
| 54. Mark Wills - She's In Love | not rated | 4:44 |
| 55. Yankee Grey - All Things Considered | not rated | 2:40 |
| 56. Billboard Top Country Singles Of 1999 - 056 - Brad Paisley - He Didn't Have To Be | not rated | 4:36 |
| 57. Billboard Top Country Singles Of 1999 - 057 - Trisha Yearwood - Powerful Thing | not rated | 2:59 |
| 58. Billboard Top Country Singles Of 1999 - 058 - Sawyer Brown - Drive Me Wild | not rated | 3:35 |
| 59. George Strait - Meanwhile | not rated | 3:31 |
| 60. Brooks & Dunn - I Can't Get Over You | not rated | 4:08 |
| 61. Reba Mcentire - One Honest Heart | not rated | 3:54 |
| 62. brad paisley - Who Needs Pictures | not rated | 4:07 |
| 63. Lee Ann Womack - Now You Don't | not rated | 2:39 |
| 64. Shania Twain - That Dont Impre | not rated | 4:36 |
| 65. Faith Hill - Breathe | not rated | 4:09 |
| 66. Reba Mcentire - Wrong Night | not rated | 2:50 |
| 67. Reba McEntire - What Do You Say | not rated | 3:29 |
| 68. Terri Clark - Everytime I Cry | not rated | 3:48 |
| 69. Billboard Top Country Singles Of 1999 - 070 - Montgomery Gentry - Hillbilly Shoes | not rated | 3:16 |
| 70. Dwight Yoakam - Crazy Little Thing Called Love | not rated | 2:20 |
| 71. LeAnn Rimes - Big Deal | not rated | 3:05 |
| 72. Faith Hill - Love Ain't Like That | not rated | 3:49 |
| 73. Billboard Top Country Singles Of 1999 - 074 - Alabama - Keepin' Up | not rated | 3:06 |
| 74. shania twain - Shania Twain - You've Got A W | not rated | 3:29 |
| 75. Mark Chesnutt - This Heartache Never Sleeps | not rated | 3:48 |
| 76. Billboard Top Country Singles Of 1999 - 077 - Clay Walker - She's Always Right | not rated | 3:27 |
| 77. Billboard Top Country Singles Of 1999 - 079 - Chad Brock - Lightning Does The Work | not rated | 3:47 |
| 78. Randy Travis - A Man Ain't Made of Stone | not rated | 3:33 |
| 79. Doug Stone - Make Up In Love | not rated | 3:57 |
| 80. Billboard Top Country Singles Of 1999 - 082 - Aaron Tippin - I'm Leaving | not rated | 3:22 |
| 81. Billboard Top Country Singles Of 1999 - 083 - The Wilkinsons - Fly (The Angel Song) | not rated | 3:42 |
| 82. John Michael Montgomery - Hello L.O.V.E. | not rated | 2:26 |
| 83. Sammy Kershaw Lorrie Morgan - Maybe Not Tonight | not rated | 4:12 |
| 84. Brooks & Dunn - Missing You | not rated | 3:48 |
| 85. Billboard Top Country Singles Of 1999 - 087 - Clay Walker - Live, Laugh, Love | not rated | 4:04 |
| 86. Billboard Top Country Singles Of 1999 - 088 - Randy Travis - Stranger In My Mirror | not rated | 3:15 |
| 87. Billboard Top Country Singles Of 1999 - 089 - Ty Herndon - Steam | not rated | 3:37 |
| 88. Patty Loveless - Can't Get Enough | not rated | 2:56 |
| 89. Kenny Chesney - She Thinks My Tractor's Sexy | not rated | 4:08 |
| 90. The Kinleys - Somebody's Out There Watching | not rated | 3:50 |
| 91. Billboard Top Country Singles Of 1999 - 093 - Dixie Chicks - Cowboy Take Me Away | not rated | 5:12 |
| 92. Shane Minor - Slave To The Habit | not rated | 3:04 |
| 93. Tim Mcgraw - My Best Friend | not rated | 4:39 |
| 94. Track 02 | not rated | 4:22 |
| 95. Tracy Byrd - Put Your Hand In Mine | not rated | 4:35 |
| 96. Billboard Top Country Singles Of 1999 - 098 - Shane Minor - Ordinary Love | not rated | 2:55 |
| 97. Kenny Rogers - The Greatest | not rated | 3:11 |
| 98. Billboard Top Country Singles Of 1999 - 101 - Mary Chapin Carpenter - Almost Home | not rated | 4:38 |
| 99. Michael Peterson - By The Book | not rated | 3:02 |
| 100. Billboard Top Country Singles Of 1999 - 103 - Lonestar - Smile | not rated | 3:24 |
| 101. Jessica Andrews - You Go First | not rated | 3:16 |
| 102. Garth Brooks in...the life of Chris Gaines - it don't matter to the sun | not rated | 4:22 |
| 103. BlackHawk - Your Own Little Corner Of My Heart | not rated | 3:25 |
| 104. Joe Diffie - The Quittin' Kind | not rated | 3:27 |
| 105. Billboard Top Country Singles Of 1999 - 109 - Keith Urban - It's A Love Thing | not rated | 3:42 |
| 106. George Jones - Choices | not rated | 3:27 |
| 107. Vince Gill - Don't Come Cryin' To Me | not rated | 3:07 |
| 108. Vince Gill & Patty Loveless - My Kind Of Woman - My Kind Of Man | not rated | 3:56 |
| 109. Sherrie Austin - Never Been Kissed | not rated | 3:35 |
| 110. Trace Adkins - Don't Lie | not rated | 4:04 |
| 111. Billboard Top Country Singles Of 1999 - 115 - Jessica Andrews - I Will Be There For You | not rated | 3:20 |
| 112. Billboard Top Country Singles Of 1999 - 116 - Brooks & Dunn - Beer Thirty | not rated | 2:37 |
| 113. Billboard Top Country Singles Of 1999 - 117 - Deryl Dodd - A Bitter End | not rated | 3:41 |
| 114. Billboard Top Country Singles Of 1999 - 118 - Shane McAnally - Are Your Eyes Still Blue | not rated | 3:46 |
| 115. SheDaisy - This Woman Needs | not rated | 3:23 |
| 116. Billboard Top Country Singles Of 1999 - 120 - Mark Wills - Back At One | not rated | 4:08 |
| 117. Billboard Top Country Singles Of 1999 - 121 - Clint Black - You Don't Need Me Now | not rated | 3:39 |
| 118. Jo Dee Messina - Because You Love Me | not rated | 3:51 |
| 119. Warren Brothers - Better Man | not rated | 4:12 |
| 120. Lari White - Take Me | not rated | 3:33 |
| 121. George Strait - We Really Shouldn't Be Doing T | not rated | 2:31 |
| 122. Billboard Top Country Singles Of 1999 - 127 - Tracy Byrd - When Mama Ain't Happy | not rated | 3:21 |
| 123. Alabama - (alabama)-small_stuff | not rated | 4:00 |
| 124. Billboard Top Country Singles Of 1999 - 129 - Jason Sellers - A Matter Of Time | not rated | 3:46 |
| 125. Billboard Top Country Singles Of 1999 - 130 - Sara Evans - Fool I'm A Woman | not rated | 3:06 |
| 126. Tracy Lawrence - Lessons Learned | not rated | 2:57 |
| 127. Chely Wright - It Was | not rated | 3:51 |
| 128. Billboard Top Country Singles Of 1999 - 134 - Aaron Tippin - Her | not rated | 3:16 |
| 129. Billboard Top Country Singles Of 1999 - 135 - Diamond Rio - I Know How The River Feels | not rated | 3:41 |
| 130. Billboard Top Country Singles Of 1999 - 136 - Toby Keith - How Do You Like Me Now | not rated | 3:28 |
| 131. Garth Brooks - It's Your Song | not rated | 4:19 |
| 132. Steve_Holy(Blue_Moon)-11-Don`t Make Me Beg | not rated | 3:26 |
| 133. Toby Keith - Getcha Some | not rated | 3:16 |
| 134. Billboard Top Country Singles Of 1999 - 140 - Neal McCoy - I Was | not rated | 3:13 |
| 135. Billboard Top Country Singles Of 1999 - 141 - Deana Carter - Angels Working Overtime | not rated | 5:21 |
| 136. (jerry_kilgore)-love_trip | not rated | 3:21 |
| 137. Billboard Top Country Singles Of 1999 - 143 - Sammy Kershaw - One Day Left To Live | not rated | 2:55 |
| 138. Billboard Top Country Singles Of 1999 - 144 - Deanna Carter - You Still Shake Me | not rated | 2:48 |
| 139. Chad Brock - A Country Boy Can Survive (Y2K | not rated | 3:59 |
| 140. Billboard Top Country Singles Of 1999 - 146 - Steve Wariner - Every Little Whisper | not rated | 3:04 |
| 141. Billboard Top Country Singles Of 1999 - 147 - Linda Davis - I'm Yours | not rated | 3:30 |
| 142. Sammy Kershaw - when_you_love_someone | not rated | 4:14 |
| 143. Martina McBride - Love's The Only House | not rated | 5:14 |
| 144. Phil Vassar - Carlene | not rated | 4:07 |
| 145. Warren Brothers - She Wants To Rock | not rated | 2:53 |
| 146. Susan Ashton - You're Lucky I Love You | not rated | 3:32 |
| 147. Travis Tritt - No More Looking Over My Shoulder | not rated | 3:46 |
| 148. Billboard Top Country Singles Of 1999 - 154 - Montgomery Gentry - Daddy Won't Sell The Farm | not rated | 4:18 |
| 149. Billboard Top Country Singles Of 1999 - 155 - Paul Brandt - It's A Beautiful Thing | not rated | 4:29 |
| 150. Jeff Foxworthy - Redneck 12 Days Of Christmas | not rated | 2:21 |
| 151. Billboard Top Country Singles Of 1999 - 157 - Garth Brooks - You Move Me | not rated | 4:29 |
| 152. Collin Raye - Start Over Georgia | not rated | 3:06 |
| 153. Billboard Top Country Singles Of 1999 - 159 - Michael Peterson - Sure Feels Real Good | not rated | 2:51 |
| 154. Clint Black - Til' Santa's Gone (Milk & Cookies) | not rated | 2:41 |
| 155. Billboard Top Country Singles Of 1999 - 161 - Bill Engvall - Here's Your Sign Christmas | not rated | 2:19 |
| 156. Billboard Top Country Singles Of 1999 - 162 - Julie Reeves - Trouble Is A Woman | not rated | 2:26 |
| 157. Bryan White - You're Still Beautiful To Me | not rated | 5:14 |
| 158. Kenny Rogers - Buy Me A Rose | not rated | 3:48 |
| 9:27:00 |
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