[3] Michigander's first song, the self-released Nineties single, debuted in 2016, followed by additional singles, including Mexico, and ATL, an Audiotree live session extended play, and the 2018 self-released Midland extended play, consisting of 6 tracks, all written solely by Singer.

[5] The EP features the single "In My Head", a collaboration with indie rock band Manchester Orchestra, and "Cannonball", a track written with Dashboard Confessional's frontman, Chris Carrabba.

[7] He and his bandmates built a following by playing opening acts for better-known bands during local stops on their tours.

[8] The song gained traction on streaming services such as Spotify and Apple Music, culminating in additional singles Mexico and ATL.

[10] The band has since maintained a busy schedule, landing slots at the 2021 Lollapalooza in Chicago, Illinois, in support of their extended play Everything Will Be Ok Eventually released in 2021,[11] and Austin City Limits in 2023,[12] in support of their extended play It Will Never Be The Same released that same year.