Judges for the 2021 Jimmys were comprised of notable theatre professionals including Tony Award-winning producers, award-winning casting experts and industry professionals. Winners, finalists, and semifinalists were selected by Kent Gash, Montego Glover, Brian Moreland, Alecia Parker, Tara Rubin, Luis Salgado, Nick Scandalios and Bernie Telsey. Preliminary judges who evaluated and cast nominees included Pun Bandhu, Rashad Chambers, Kristian Charbonier, Stephanie Klapper, Kevin Metzger-Timson and Thoms Sesma.

The annual Broadway-focused talent showcase included medley and production performances by all 72 nominees from 36 regions around the US and featured solos by select finalists. In 2021, all coaching, rehearsals, and activities took place online. The industry coaches who mentored the nominees included: Jenni Barber, Janet Dacal, Eden Espinosa, Maryann Hu, Adam Kantor and Eliseo Román. Michael McElroy was the coach coordinator.

The Jimmy Awards was directed by Van Kaplan and choreographed by Kiesha Lalama. Michael Moricz was the musical arranger and conductor, and Mary Jane Brennan was the writer. All four have been with the Jimmy Awards for all 12 years of the program.

The 2021 Jimmys also welcomed eight student reporters from Regional Awards Programs around the country. During the Jimmy Awards production week, these junior journalists sat in on many of the online sessions and rehearsals attended by the performer nominees. Each student reporter submitted a series of videos providing “on the ground” reporting about the nominee experience and how the production was put together. In addition, the student reporters met with industry professionals who provided first-hand experience and advice on the digital and press landscape surrounding the Broadway industry.