Raphael, a.k.a. Wiseguy, is voiced by Hank Azaria. He first appeared as the chauffeur hired to take Homer to the prom (despite that Marge was going with Artie Ziff) in the second season in "The Way We Was", but he has held numerous other jobs in the series. Simpsons sound editor Bob Beecher commented on alt.tv.simpsons that, "He doesn't have one name. His character's name always fits the scene so he's gone by many names, 'Clerk', 'Shopkeeper', etc. But in the script the direction given to the voice is 'Wiseguy Voice'. So call him 'Wiseguy' if you want." Azaria does a Charles Bronson-impression for the voice. In "Simpsoncalifragilisticexpiala(Annoyed Grunt)cious", Al Jean and Mike Reiss had Azaria voice a Simpsonized Charles Bronson as a reference to this. As with his profession, the character's physical appearance varied widely with regards to hair and facial features for a number of years, with the voice being the only constant; eventually, he was standardized as a balding, greying man with a moustache. Wiseguy has been dubbed "The Sarcastic Middle-Aged Man" by the show's Internet fans. In "Day of the Jackanapes", Sideshow Bob calls Wiseguy by the name "Raphael".
Read more about this topic: List Of Recurring The Simpsons Characters