His mother was a nurse and his father an architect. His father's stereo and record collection inspired Moakler,[3] who started playing guitar and writing songs at age 14, and forming his first band in middle school.[1] He played throughout Pittsburgh during his high school years. He graduated from Bethel Park High School in 2006 and turned down an independent record deal to move to Nashville.[1]
Moakler attended Belmont University in Nashville, taking classes during the week and playing shows on the weekends. After two years he left school to focus full-time on his music career.[1]
As a performer and recording artist, Moakler's work has been praised by Rolling Stone Country as "thoughtful singer-songwriter fare in the blue-collar vein."[9] His first record, All the Faint Lights, was self-published. In 2011 he formed his own label, Free the Birds, and released two more albums independently, Watching Time Run and Wide Open. The label also used the money raised to combat sex trafficking.[10] In 2014, Beth Laird of Creative Nation sought out Moakler and retained him under management.[11] In 2016, he worked with Creative Nation producer Luke Laird on a self-titled EP, whose songs made up the first half of his 2017 album, Steel Town.[6] Moakler says the latter album was inspired by his upbringing in Pittsburgh.[12] It has been called a more personal album,[1][6] as well as his "most country" album.[13][14] The first single, "Suitcase," became his first radio hit and first music video.[6] The second single was "Love Drunk," followed by a third single, "Wheels."[13] Moakler released his fifth album, Born Ready, in 2018. The album has been critically acclaimed,[15][16] with Bobby Moore praising its "pop gems that clear the barrier between Americana and the country charts."[17]
Moakler has been named an artist to watch by numerous outlets,[12] including Rolling Stone Country,[9]Spotify,[18] and Taste of Country.[5] He has been heavily promoted by SiriusXM’s senior director of programming J.R. Schumann[19] on station “The Highway.” The station also had him open their inaugural “The Highway Finds Tour.”[12][20][8] Moakler made his Grand Ole Opry debut on March 19, 2016.[21] He opened for parts of Dan + Shay's "Obsessed Tour", Old Dominion's "Meat & Candy Tour",[22]Willie Nelson's "God's Problem Child Tour", and Tim McGraw and Faith Hill's "Soul2Soul World Tour".[23] Moakler toured in late 2017 and late 2018 on the "Hometowns and Campgrounds Tour,"[24] and he headlined in spring 2018 on the "Born Ready Tour."[25]
Moakler's music has been featured in several movies, TV shows, and commercials.[26] Two of Moakler's songs appeared in the movie October Baby, and two songs also featured in the Netflix show The Ranch. In 2017, Mack Trucks commissioned him to write and perform a song, “Born Ready,” for the release of their Anthem truck series.[27][28]