As a side project Glover raps as Childish Gambino, a name he found from a Wu-Tang Clan name generator. He released an album entitled "Sick Boi" on June 5, 2008, in which he thanks himself. On September 17, 2009, 'Childish Gambino' released the album Poindexter. A pair of mixtapes entitled I Am Just A Rapper, and I Am Just A Rapper 2 were released in close succession in early 2010. The track listings for his albums on I AM JUST A RAPPER and I AM JUST A RAPPER 2 consist of the name of the song "he" raps, followed by the song he raps over. His latest and third album, Culdesac, was set to be released on July 2, 2010, but a couple of last minute additions caused the album to be delayed for a day. The album was made available on July 3.Glover has stated in interviews that on "Sick Boi" and "Poindexter" he felt he had to hide behind gimmicks, such as pink hoodies. But with his subsequent projects, he has touched on more personal subject matter, including family, schoolyard bullying, troubled romantic relationships, suicidal thoughts and alcoholism. He has disowned his 2002 album, The Younger I Get, as the too-raw ramblings of what he calls a "decrepit Drake."
On December 1 2010, Glover released the first track off of his EP titled "Be Alone". He released the next track, "Freaks and Geeks", as well as a five-song track list, on February 11. On February 25 2011, Donald released the dates for the IAMDONALD tour and also his very first music video for "Freaks and Geeks. "On March 8, 2011 Donald released his newest EP via his official website.
Glover also refers to himself as Cheezy, Bambino X, Bam-B, Sir Durton Cloud 9, Ms. Long-Lady Stanhope, Elroy, and Bambini.