1996
Brooks & Dunn released a cover version of "My Maria" (originally a 1973 hit for B. W. Stevenson) which gave the duo their tenth country #1 hit. The #1 country song of 1996 according to Billboard, and the track won the duo its second Grammy Award for Best Country Performance by a Vocal Group or Duo.

2000
Toby Keith was at #1 on the US Country chart with "How Do You Like Me Now?!" Taken from his album How Do You Like Me Now?! The song spent five weeks at #1 on the chart and became his first major crossover hit.

2000
Dixie Chicks fifth studio album Fly was at #1 on the country chart. The album earned 4 Grammy nominations in 2000, and the group won 2: Best Country Performance by a Duo or Group with Vocal for "Ready to Run" and Best Country Album. It was also nominated for Album of the Year and the writers of "Ready to Run", Marcus Hummon and Martie Seidel were nominated for Best Country Song.

2001
Toby Keith's father was killed in a car accident on Interstate 35. On December 25, 2007, the family was awarded $2.8 million for the wrongful death of H.K. Covel, (Keith's father). Elias and Pedro Rodriguez, operators of Rodriguez Transportes of Tulsa, and the Republic Western Insurance Co. were found liable as they failed to properly equip the charter bus with properly working air brakes.

2012
Wild Eagle opened at the Dollywood theme park in Pigeon Forge, Tennessee, the first Bolliger & Mabillard Wing Coaster in the United States. It was also the biggest investment in Dollywood history.

2018
Bebe Rexha and Florida Georgia Line spent the eleventh week at the top of the charts with "Meant to Be" surpassing Taylor Swift's "We Are Never Ever Getting Back Together" as the longest-running #1 song on the chart for a lead female artist.