|Studio 60 On The Sunset Strip character|
|Last||What Kind of Day Has It Been|
One of the "Big Three" cast members of Studio 60, Simon Stiles joined the show in 2001. He was initially resentful, having lost out on a significant movie role to Jamie Foxx and felt that, as a graduate of the Yale School of Drama, he didn't belong on a sketch-comedy show. Since then, however, he's found his niche in the cast and has developed a deep loyalty to both the show and his fellow cast members. Before he was cast in Studio 60, Simon was paying his dues by doing standup comedy three sets a night for ten dollars at various nightclubs around Los Angeles.
He sometimes feels limited by his comedic skills, conscious of the fact that he isn't able to do the humorous "voices" he thinks Ricky and Ron have been pushing for.
As he told Matt in "The Wrap Party", Simon grew up in South Central Los Angeles amid gang violence and poverty. At the age of fifteen, he witnessed the shooting of one of his friends. In turn, they planned on a violent rebuttal with Simon planning on being part of it. But the leader of the group forbid Simon from going with them for fear of watching Simon throw away his future. As a result, many of his childhood friends are currently incarcerated, with Simon himself being the only one who really made something of himself. As a result, Simon feels a sense of guilt and responsibility to do what he can to help out others who grew up in the same area. Simon's background has several elements in common with the childhood of D.L. Hughley, the actor who plays Simon.