Suggestions by @the_critic_ruben_jr

Mark Gatiss

as Calendar Man in Richman’s: Calendar Man (Horror)

Dennis Quaid

as Brian in Richman’s: Self Help (Original)

Tessa Thompson

as Teresa in Richman’s: Self Help (Original)

Lily Collins

as Sally in Richman’s: Self Help (Original)

Ella Purnell

as Sally in Richman’s: Self Help (Original)

Andrew Garfield

as Tony in Richman’s: Self Help (Original)

Sam Raimi

as Director in Richman’s: Self Help (Original)

Osgood Perkins

as Director in Richman’s: Mystery Flesh Pit (Original)

Liana Liberato

as Liv in Richman’s: Mystery Flesh Pit (Original)

Kurt Russell

as Frank in Richman’s: Mystery Flesh Pit (Original)

Dylan O'Brien

as Kenny in Richman’s: Mystery Flesh Pit (Original)

Dr. Jekyll and Mr. Hyde (1931)

as Influences in Richman’s: Mister Negative (Horror)

Andy Muschietti

as Director in Richman’s: Mister Negative (Horror)

Keanu Reeves

as Count Nefaria in Richman’s: Mister Negative (Horror)

Peter Capaldi

as Silvermane in Richman’s: Mister Negative (Horror)

Anthony Molinari

as Hammerhead in Richman’s: Mister Negative (Horror)

Daniel Wu

as Mister Negative in Richman’s: Mister Negative (Horror)

Jill Talley

as GLaDOS in Richman’s: Portal 2 (Live Action)

Jason Lee

as The Spot in Richman’s: The Spot (Horror)

Andy Muschietti

as Director in Richman’s: The Spot (Horror)