Leonardo Leonardo was specially created for the television show. He is a local millionaire who frequently visits the Quick Stop, run by rival clerks Dante Hicks and Randal Graves, after his own creation, the Quicker Stop, failed when Jay and Silent Bob blew it up.
Leonardo Leonardo is the great-grandson of Bernardo Leonardo who bought the City of Leonardo from Indians for $14,800,000. Leonardo himself later led an expedition into Canada where he accumulated a vast fortune in exchange for the polio virus. The beginning of the Clerks television series coincides with Leonardo's homecoming.
Besides previously owning the Quicker Stop, Leonardo is also the owner of his own office building, the Leonardo Tower, and has his own Little League baseball team who won the Little League World Series under coach Dante Hicks.
He often tries to flaunt his status as a man of importance due to his extreme wealth but is quickly and often pointed out as a loser, as far as millionaires go. Leonardo is not too bright as pointed out when he ate spoiled "Descreeto Burritos" because he thought they were "the expensive kind". He poses for magazines such as Pet Store Weekly instead of acclaimed work such as Fortune or People.
There are several references to Leonardo being gay, after a picture almost appeared in his obituary of him, Elton John and Andy Warhol partying at the infamous Studio 54. There was also a reference to Leonardo sleeping with Dante after their high school reunion. Also, when asked if hiring the clerks was some sort of "Gay Thing," he immediately replied no. When asked if he was certain, he very hesitantly said yes.
He is upstaged by Randal and Dante in several episodes, always replying afterwards: "Well played, clerks."
Leonardo Leonardo is always accompanied by his bodyguard (and publicist) Plug, his right-hand man who talks like a robot (and, in fact, is one). Plug is a parody of the villain Oddjob from the James Bond movie Goldfinger, and his name is taken from one of Antonio Fargas' bodyguards in Cleopatra Jones.
Leonardo originally was to be voiced by British actor Alan Rickman, who starred in Smith's film Dogma. It was Smith's intention to base Leonardo Leonardo on the Die Hard villain Hans Gruber, who was also played by Rickman. Rickman, however, was concerned that he forever would be typecast as Gruber, so the ABC animators started reanimating the character. Eventually, the character was changed to look nothing like Gruber, and ABC sent a memo informing that they would no longer let Rickman voice the character. Baldwin was then hired and the character's design was returned to its original state.