Augustine began rapping while in high school. He began publicly performing while attending LSU. After graduating from LSU in 2008, he started teaching middle school math in Baton Rouge. By the end of 2008, he had released three mixtapes: It's Only Tha Beginning, Still We Rise and I Am Who I Am. Dee-1 has been featured in national media outlets such as CNN, Billboard, and the Washington Post. He has also received attention from Louisiana newspapers and music magazines. After two years of teaching, he resigned before the 2010–2011 school year to focus on his music as a career.
Music career
His first studio album, David & Goliath, was released April 13, 2009. In August 2009, Dee-1 released a Saints-themed song with trumpet player and Rapper Ty Ochsen, titled "Bring Em to the Dome". Additionally, Dee-1 has performed alongside nationally touring acts such as Lil Wayne, Lupe Fiasco, Drake, Trey Songz, Akon, The Roots, Mýa, The Clipse, Musiq Soulchild, Fat Joe, Lil Boosie, Juvenile, Big K.R.I.T. and Big Boi. In October 2010, he was named Artist of the Year at the NOLA Underground Hip Hop Awards. Dee-1 majorly rose to hip-hop's spotlight after the release of his song and music video, "Jay, 50, & Weezy" in 2010. The single received national attention and was praised for its narrative-driven storytelling and “sheer audacity that he displayed by calling out three of the game's biggest rappers, but mostly because of the song's strong message.” In the same year, Dee-1 released his fourth mixtape, I Hope They Hear Me Vol.1.The project received positive attention, and after his Vol 1.5 installation to the mixtape series, he released I Hope They Hear Me Vol. 2. With acclaimed tracks, such as "Jay, 50 & Weezy" occupying the 18-song track list, Dee-1's collaboration with Mannie Fresh made for another high-profile record from the project, "The One That Got Away". The track was produced by Flight School Productions complete with a music video for the 2011 single. In 2011, Dee-1 toured with Atlanta rappers Killer Mike and Young Dro, as well as the southern California-based rap groupPac Div. Following that tour, between 2011-2013, he has also toured with artists such as Macklemore, Murs, and Lecrae. Dee-1 developed a close relationship with Chicago rapper Lupe Fiasco while joining him on the Tetsuo Youth Tour of 2013 as well. Dee-1's unique artistry brought him to BET's 2014 Hip Hop Awards along with O.T. Genasis, Lil Mama, Logic and Detroit Che. Dee-1's The Focus Tape helped sustain his career momentum next, released in 2012 and featured a handful of hip-hop's biggest names; "Work" featuring Lecrae, "The Man In My City" featuring Juvenile and Mannie Fresh, "The Very Best" featuring Yassin Bey and Mannie Fresh, and "Never Clockin Out " featuring Killer Mike name a few. His released the consciously-driven singles such as "You Stupid Fool" and "Shut Up And Grind". After signing with RCA Inspiration in 2013, he released his first EP, 3s Up, featuring six tracks and heralding Dee-1's three-piece motto: "Be Real. Be Righteous. Be Relevant.". The EP peaked at No. 9 on Billboard's Top Rap Albums in 2015. "Against Us" was the first single from the EP, released in 2014. The track delivered a powerful testament combating the ills of society and the Hollywood industry. Dee-1 created the "Against Us " in 2016 and enlisted Big K.R.I.T. and Lupe Fiasco as featuring acts. Among other topics, he addressed his affecting lyrical subject matter and personal faith, like that of "Against Us", on popular radio segment Sway's Universe with Sway Calloway. He discussed the importance of improving his personal life and increasing his faith among some of the music industry's moral corruption. The interview inspired the track on 3s Up, fittingly titled, "The Sway Interview". Dee-1 admitted that he was spiritually in a dark place during the time in his life when the interview was conducted. He credits it as "life-saving", to which Calloway praised as a "Grammy" honor for him. "I'm Not Perfect " from the 3s Up EP also emphasizes the depth of his Christianity. What would have been Dee-1's latest mixtape, Separated at Birth, was influenced by the sound and production of Lil Wayne, scheduled to be released in 2015. Due to conflicts with the mixtape's lyrical content and Cash Money Records, Lil Wayne's home label, the project was not publicly released. Dee-1 released "Sallie Mae Back" in 2016, a hyper-energetic track celebrating the completion of his student loan payoffs. In addition to his own budgeting, he used a part of his label signing advance to pay off the loans. The track received critical acclaim from CNN, ESPN, Forbes and Time magazine. The Washington Post called it the "anthem of a generation" and landed Dee-1 a seat on Fox's leading talk show, The Real, as well as ESPN's His & Hers with Michael Smith and Jemele Hill. The success of the track also led to ESPN recruiting Dee-1 for the theme song, "We Are The Undefeated", of its sports, race, and culture website, The Undefeated. He also penned lyrics for the "F.A.S.T. Song", a track for the American Heart Association raising stroke awareness. Dee-1 headlined his first nationwide tour of 2016 in 2016 titled The Slingshot David Mixtape Tour, following the release of The Slingshot David Mixtape in July that year. His first studio album under the RCA imprint, Slingshot David, was released on November 10, 2017. The album's lead single, "Hood Villains", was handpicked by Lupe Fiasco, and the project boasts names such as Sevyn Streeter and Avery Wilson. In 2019, it was announced that Dee-1 left RCA Records and started up his own independent label called Mission Vission Music. He released his second studio album God and Girls under the new label. On April 30, 2020, Dee-1 released a solo project titled Timeless, ahead of his upcoming collaborative album with Murs.
