Sean “P. Diddy” Combs – Gladiator

To attend a 2004 party in New York, Sean John Combs, best known as P.Diddy, added his own twist to the Gladiator costume. While his attire is far from historically accurate, the bright colors and mask sure make it worth remembering. We also can’t leave out mentioning the fun shoes.

Over the years, his costumes evolved from fun to scary, and in 2018, he dressed up as the killer clown, It from the movie of the same name. In 2022, he made headlines for taking on the role of a peacemaker between Will Smith and Chris Rock following their dispute at the Oscars.