A year later, ILoveMakonnen presented mixtapes 3 Suns and Drink More Water 2. In 2014, he released Drink More Water 3 and Drink More Water 4. The same year, the musician signed contracts with OVO Sound and Warner Bros. and recorded his debut LP, iLoveMakonnen. The album featured such hits as "Too Much", "Club Goin' Up on a Tuesday", "Tonight", "I Don't Sell Molly No More", and "Meant to Be". “Tuesday” topped Billboard’s R&B Songs Chart and became platinum in the USA. It seems to be the most popular artist’s work to date. The album itself reached the 48th spot of Top R&B/Hip-Hop Albums and settled on the 72nd spot of Billboard 200.
Other artists often invited Makonnen as a guest for their songs. He helped record "Nokia" for Father L1L, "FriendsMaybe" for Rome Fortune, "Look at Wrist" for Father, "I Understand" for Key!, "Swerve" and "Syrup in My Soda" for Mike WiLL, as well as a remix for Tunji Ige’s " Day2Day". At that time many fans tried to book ILoveMakonnen for their events, but he was rarely available.
In 2015, the same two labels helped the rapper record his second LP, iLoveMakonnen 2. It was less popular than the predecessor, didn’t make it into Billboard 200 but climbed to the 40th position of Top R&B/Hip-Hop Albums Chart.
The same year, ILOveMakonnen recorded two more mixtapes, Drink More Water 5 and Whip It Up. He also worked with many artists to help record their songs. At that time, it seemed as if the rapper worked more on other musicians’ songs than he did on his own. However, he diligently continued releasing mixtapes. By 2016, he recorded Drink More Water 6 and Red Trap Dragon (with Danny Wolf). The rapper stopped working with labels and started releasing the albums independently. He continued working with other artists as well.
In 2017, the singer released his third LP, Fun Summer 17 Vol. 1. A year later, another LP, ILOVEMAKONNEN X RONNY J, recorded with Ronny J, came out. Both albums were released independently and neither made it into the charts. The same year Makonnen openly announced on Twitter that he is gay.
In July 2018, the rapper presented one more independent album, iLOVEAMERICA. So far, it hasn’t made it into the charts but managed to gain popularity among the singer’s numerous fans.
ILoveMakonnen works hard on promoting his albums and recording new ones. He enjoys performing live.