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Luke Bryan makes Billboard history with 'Play It Again' & 'This is How We Roll'

LAS VEGAS, NV - MAY 18: Singer Luke Bryan poses in the press room during the 2014 Billboard Music Awards at the MGM Grand Garden Arena on May 18, 2014 in Las Vegas, Nevada.
Photo by Frazer Harrison/Getty Images

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 No. 1 spot on Billboard's Country Airplay chart with "Play It Again" and "This Is How We Roll" landing in the No. 2 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 No. 1 and No. 2 positions on the Hot Country Songs chart for four of the last five weeks with "Play It Again" and "This Is How We Roll," which makes Bryan the third artist since 1958 to land in the No. 1 and No. 2 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." Swift did it when "We Are Never Ever Getting Back Together" reached the No. 1 spot, and when "Red" made its debut by landing in the No. 2 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 and claiming the Top Country Album category for Crash My Party. Bryan hit the stage for two performances during the award show as well, performing his hit “Play It Again” and joining fellow Billboard Music Awards winners Florida Georgia Line, who received the win with “Cruise” in the Top Country Song category, for a show stopping performance of "This Is How We Roll."