In 2004, the prom was awarded "Best Prom" by Reader's Digest as part of their "America's 100 Best" feature. In 2004, singer-songwriter John Mayer performed for a crowd of nearly a thousand students. Various other artists, including Maroon 5 have also performed at previous proms. In 2017, TV personality DJ Pauly D of Jersey Shore (TV series) fame made an appearance with Questlove. Pauly D performed again in 2018, preceded by singer and actor Drake Bell, best known for his role as Drake Parker on the Nickelodeon television show Drake & Josh. In 2019 Pauly D once again performed and rapper Desiigner made an appearance in front of an excited Pennsbury Prom audience.