After 36 seasons, MTV’s The Challenge is a reality television institution: No TV show has pitted more former, current, and future reality stars against one another—often at the same time. The first iteration of the show came when the casts of The Real World: Boston and Road Rules: Islands met while the Real World cast vacationed in Puerto Rico. The Real World alumni pranked their Road Rules counterparts during Challenge 2000. While in Miami during Challenge 2000, The Real World team organized a fake mission to trick their Road Rules opponents. As of 2021, Devenanzio—who originally appeared on The Real World: Key West in 2006—has made the most appearances on The Challenge, with 20.