He was originally nicknamed “Puffy” at school because he always puffed his chest out. And this led him to adopt the moniker of “Puff Daddy” in the early ’90s. Then in 2001 he changed it to “P. Diddy,” which was the name that long-time compatriot Biggie Smalls had called him by.
He subsequently shortened this to “Diddy” in 2005, before returning to his roots in 2008 with “Sean John,” which are his real first and middle names. However, in 2012 he would go back to a more out-there title yet again, this time calling himself “Swag,” albeit for just one week.