Barack Obama be scared o' me cuz I don' swallow knowledge and I spit it fo' free!
— Dean Pelton
Pelton trying to compose another rap masterpiece.
In the study group's fifth year at Greendale, Dean Pelton had to tell Jeff and Hickey that payroll had been delayed. In order to make the announcement more palatable to them, he dressed up as a "Payday" candy bar to deliver the news through a free style rap. He arrived in costume at a Save Greendale Committee the two faculty members were attending accompanied by a keyboardist. After making a brief statement about the payroll delay, he then launched into his free style rap. What started out as a pleasant and upbeat ditty soon turned into a hard and fierce rhyme. Pelton stopped rapping and ran out of the room overcome by his passionate performance. The "Payday Apology Rap" was first heard in the Season Five episode "VCR Maintenance and Educational Publishing."
The Payday candy bar was invented in 1932 by the Hollywood Candy Company of Minneapolis, Minnesota. The inventors didn't know what to call their new creation. Finally one of them suggested Payday since it just happened to be payday at the company. The name stuck (source).
Jim Rash joked at the 2019 Vulture Festival Community reunion that he did the entire rap in only one take: according to Gillian Jacobs and a fan named Rebecca Coleman who visited the set that day, the scene actually took multiple takes because no one could keep a straight face. Jacobs recalls ruining several takes because she could not stop laughing, and even in the finished episode she is clearly smiling when turning back to the camera.