Luke Bryan follows up his double “Billboard Music Awards” wins and performances by adding a new Billboard history making moment to his career. Billboard reported on May 20, 2014 that Bryan reached a record breaking milestone by reaching the number one spot on Billboard's Country Airplay chart with "Play It Again" and "This Is How We Roll" landing in the second spot on the chart with Florida Georgia Line.
That makes Bryan the first artist to hold the top two positions on the chart simultaneously since it began on Jan. 20, 1990. Bryan has also been sitting in the number one and number two positions on the Hot Country Songs chart for four of the last five weeks with "Play It Again" and "This Is How We Roll" with Florida Georgia Line which makes Bryan the third artist since 1958 to land in the number one and number two spots after multiple country rankings were moved into a single chart.
Buck Owens and Taylor Swift are the only two other artists that have reached the double song milestone on that chart. Owens made it happen in 1964 with "Together Again" and "My Heart Skips a Beat" and Swift did it when "We Are Never Ever Getting Back Together" reached the number one spot and "Red" made its debut by landing in the number two position for the week of Oct. 20, 2012.
Bryan also added two more trophies during the “Billboard Music Awards” by walking away the winner as the “Top Country Artist” winner and claiming the “Top Country Album” category for “Crash My Party.” Bryan hit the stage for two performances during the “Billboard Music Awards” performing his hit “Play It Again” and joining fellow “Billboard Music Awards” winners Florida Georgia Line that received the win with “Cruise” in the “Top Country Song” category for a show stopping performance of "This Is How We Roll."