iLoveMakonnen attracted an online following with his surreal and lackadaisical mic approach before Drake turned his "Club Goin' Up on a Tuesday" into "Tuesday" (2014), a Top 20 and platinum pop hit nominated for a Grammy in the category of Best Rap/Sung Collaboration. The whimsical singer/rapper and producer has since built a large discography that includes over 20 mixtapes and EPs, and numerous collaborations highlighted by featured appearances on gold singles headlined by Carnage and Lil Peep, namely "I Like Tuh" (2015) and "I've Been Waiting" (2019). Following stints with Drake's OVO Sound and major-label Warner Records, Makonnen released his debut LP, My Parade, in 2021.

Makonnen Kamali Sheran spent the first years of his life in Los Angeles, and at the age of 13 moved near Atlanta. He got deep into a variety of genres by his late teens. Recording on his own, he uploaded songs to MySpace, and made other connections by interviewing artists and public figures for his blog. Across the first few years of the 2010s, Makonnen issued a slew of mixtapes, including the first volumes in his Drink More Water series. Miley Cyrus boosted his profile in mid-2014 by posting an image of the recently released I Love Makonnen EP on Instagram. More significantly, the EP attracted Drake, who inserted himself into a remix of "Club Goin' Up on a Tuesday" and in September released the result on his Warner-distributed OVO Sound label. Retitled "Tuesday," the track reached number 12 on the Billboard Hot 100 two months later, and was Grammy-nominated by the time it achieved platinum status. The parent EP, spiffed up by OVO Sound for commercial release in December, entered the Billboard 200 at number 72.

While signed to OVO Sound, Makonnen continued in 2015 with I Love Makonnen 2, his second charting EP, assisted on the gold single "I Like Tuh" by Carnage, and by the end of the following year had also offered the fifth and six volumes of Drink More Water and the Rich the Kid collaboration Whip It Kid. Drink More Water 6 was his first recording for Warner Records proper, and was followed by an assortment of self-released material before a return to Warner in 2019 with M3, an EP featuring Gucci Mane on the track "Spendin'." Also in 2019, Makonnen hit the Hot 100 again as a featured artist on Lil Peep's "I've Been Waiting." After a comparatively quiet 2020, Makonnen re-emerged on a new and independent label in April 2021 with My Parade, his first album. Another EP, Monster In the Woods, appeared that same year, followed in 2022 by singles like "Plastic" and "All My Shit is Stupid" featuring Young Boy Never Broke Again. ~ Andy Kellman, Rovi