"Tuesday" also received a nomination Best Rap/Sung Collaboration at the 57th Annual Grammy Awards, and served as the lead single for his likewise re-issued self-titled debut extended play (2014), which moderately entered the Billboard 200.

Makonnen also created a blog, where he would post interviews with musicians such as Lil B and Soulja Boy Tell'em.

[9] After a period under house arrest following the fatal accidental shooting of a friend,[10] he enrolled in a cosmetology school and became a part of a group called Phantom Posse.

Later, after recording six songs together, Metro brought these fellow Atlanta producers Sonny Digital and 808 Mafia, who were all unusually impressed with him.

Two days later, Makonnen recorded the song, titled "Don't Sell Molly No More" with Sonny Digital, which would later launch his music career.

He started gaining local fame within the community with songs such as "Living on the Southside", "Sneaky Lady" and "My New Friend".

In July 2014, the singer released his self-titled EP iLoveMakonnen, which included the singles "Tuesday" and "I Don't Sell Molly No More".

[13][15][non-primary source needed] On August 15, 2014, Vice included his song "Whip It" in their Staff Picks for the Week list, commenting: "Makonnen's voice is incredible!

"[6] The remix, simply titled "Tuesday" went viral and led to increased media interest in iLoveMakonnen.

On September 1, 2014, it was announced that Makonnen had signed to Drake's label OVO Sound, which is distributed by Warner Bros.

[19] In an interview with The Fader in December 2015, more than a year after signing to Drake's OVO Sound, Makonnen said the label delayed tracks from iLoveMakonnen 2 from coming out.

The song "Second Chance," for example, was finished in January 2015 and intended for a summer release,[20] but ended up being self-released by Makonnen in November 2015.

"[20] Makonnen also claimed "extra bullshit in the industry" stopped "Teach Me How To Whip It" and "No Ma'am" from getting radio play.

"[20] On February 8, 2016, it was announced that alongside Travis Scott and Vic Mensa, Makonnen would be part of the "Wangsquad", an Alexander Wang campaign.

[22] On April 18, 2016, Makonnen parted ways with Drake's label OVO Sound, saying the "choice to be solely on Warner Bros. Records was the right thing for me and for my best interest.

"[23] On May 7, 2016, Makonnen announced he would be retiring from music to focus on acting but released a new song shortly after, with confirmation of a new project.

[25] On August 17, 2018, Makonnen announced a single he co-wrote titled "Falling Down", a reworking of "Sunlight On Your Skin" that he recorded with Peep during the sessions in London.