The band began its career in 2015 and signed with Steady Records, which belongs to Emi Universal. In addition to the label, Drew Dirksen was created by fellow group The Vamps. The Vamps' Austin Corini and Levi Jones helped the group form. Drew Dirksen was selected from an audition with the help of other members of the band. Their first two albums, Young Love and MCMXCVI, were released in 2016 and 2017.