On March 28, 2016, rapper Big Sean and singer-songwriter Jhené Aiko announced that they were forming a duo, called TWENTY88. The Los Angeles songstress and the Detroit rapper have previously collaborated on the songs "Beware" (with Lil Wayne) from Sean's second album Hall of Fame (2013), as well as "I Know" from Sean's third album Dark Sky Paradise (2015). According to a press release from Tidal, the album will tell the story of the highs and lows of a relationship, with insights into conflict, memories, love, sex and more.
On March 29, Sean and Aiko appeared together on the cover of Flaunt Magazine to promote the album, TWENTY88. For the cover story, they talked about the origin of the duo TWENTY88, and their vision for the album. Jhene Aiko says: "Music now doesn't really cater to the feelings of a real relationship. It's all about trapping and bragging. I feel like this project is something that's needed right now. Especially a whole project, is just good for people to see. That duality is a perfect combination. It's a 70's aesthetic, but we're in the future." They draw from various influences: Blaxploitation films like Coffy, where a smart, strong Pam Grier empowers herself and goes vigilante against organized crime, James Bond films: style, luxury, and debonair masculinity are definitive parts of Sean's undeniable appeal and even Ex Machina.