Pistol Annies made their debut on April 22, 2011, on the Academy of Country Music's Girls' Night Out: Superstar Women of Country on CBS, performing "Hell on Heels". The women gave themselves the nicknames "Lonestar Annie" (Lambert), "Hippie Annie" (Monroe), and "Holler Annie" (Presley). They released the album Hell on Heels on August 23, 2011, with the title song being released for purchase on their website two months earlier, on June 12. After a series of performances during Lambert concerts, the Pistol Annies performed three sold-out headlining shows in December 2011 with guest performances by John Fogerty and Blake Shelton.
Annie Up, the trio's second studio album, was released on May 7, 2013. It was preceded by the lead single "Hush Hush," which became the Pistol Annies' first chart entry on the U.S. BillboardHot Country Songs chart. The group is also featured on the Blake Shelton single, "Boys 'Round Here," from his 2013 album, Based on a True Story….
The group cancelled all tour stops in June 2013, according to their record label, "due to unforeseen circumstances". Lambert still performed as a solo act in June. Monroe went to the Mermaids of Alcatraz Tour with Train. In August 2014, Angeleena Presley confirmed that the group was on temporary hiatus, saying that due to the success of Lambert's and Monroe's solo careers, the band "just had to take a little break but never say never."