2012: Early career

Don Trip's career began at 15, when he started rapping.^[6] After working on his craft, he began to release mixtapes and singles in very late 2000s, leading to a string of 9 projects being released between October 2010 (Crossface Crippler)^[8] and February 2012 (Guerilla).^[9] Releasing his mixtapes on websites such as Datpiff and HotNewHipHop, Don Trip began to amass a following as a street rapper. However, his song "Letter to My Son," (originally released in 2009) went semi-viral on YouTube, fueling his transition toward mainstream hip-hop.^[7] The song, which detailed Trip's struggle with being unable to see his son due to court ruling, was lauded for its accurate depiction of a hardship not often portrayed in rap music. In 2012, hot on the heels of "Letter to My Son," Don Trip was named one of XXL's 2012 freshmen, alongside Future, Danny Brown, Hopsin, and more.^[5] Soon after, he was signed to Epidemic Records, a joint enterprise between production duo Cool & Dre and Interscope Records.^[4]

2017—present: Step Brothers

Prior to his signing at Interscope, Don Trip scored big with his collaborative Step Brothers mixtape with Starlito.^[10] Released in 2011, the mixtape was peppered with references and in-jokes relating to the Judd Apatow movie Step Brothers, and gained a cult following among the rap community. A few months before the mixtape's release, Starlito and Don Trip were introduced to each other by Yo Gotti, with whom Don Trip was touring.^[7] Both rappers were already familiar with the other's music, and after discovering their musical compatibility, decided to make a joint project.^[11] Three studio sessions later, Step Brothers was fully recorded. Due to the success of the mixtape as well as their collaborative chemistry, Starlito and Don Trip continued to collaborate, releasing the Step Brothers 2 mixtape in 2013.^[12] While Don Trip was based in Memphis while Starlito was based in Nashville, the two continued to meet up to record, never emailing each other songs back and forth.^[13] Eventually, in 2017, the two linked up again for the third installment of the Step Brothers series,^[14] preceded by the Karate in the Garage collaborative mixtape.^[15] Released independently, like the two previous mixtapes, Step Brothers 3 received widespread critical acclaim from publications such as Pitchfork,^[16] XXL,^[17] and USA Today.^[18]

Mixtapes/EPs