After collaborating with other artists during her early to mid-teens, she took a brief hiatus to finish her education. In 2011, she released her comeback mixtape, Sailing Soul(s), comprising dreamy, minimal R&B vocals; it was entirely written by Aiko and featured collaborations with Drake, Gucci Mane, and Kanye West. In 2012, she signed with Def Jam through No I.D.'s ARTium imprint and released the single "3:16AM." The following year proved to be pivotal for Aiko -- she was featured on Big Sean's Top 40 hit "Beware" and teamed up with Drake for an appearance on his highly anticipated album Nothing Was the Same. Critics praised her performance with Drake, which raised her profile globally. In November 2013, she released her debut EP, Sail Out, which included the tracks "Bed Peace" (featuring Childish Gambino) and "The Worst," the latter of which peaked at number nine on Billboard's R&B chart. The album also garnered two Grammy nominations, including Best Urban Contemporary Album and Best R&B Song for "The Worst."

Souled Out, her proper debut album, was released the following September and hit number three on the Billboard 200. The album also spawned several singles, including "To Love & Die," "The Pressure," and "Spotless Mind." Aiko then collaborated with rapper Big Sean on the 2016 side project TWENTY88. Several more singles followed, including "Maniac," "Hello Ego," and "While We're Young," the last of which was featured on her 2017 full-length, Trip. ~ Aneet Nijjar, Rovi