Loogie (or Luigi) made his first appearance in "The Tooth Fairy Tats 2000". When the boys try to make money by snatching tooth fairy money left underneath other boys' pillows, they encounter another set of boys trying to do the same thing. These rivals bring the boys back to Loogie, whereupon they learn that the Tooth Fairy business is actually a crime syndicate, with Loogie being portrayed as a youth Mafia kingpin. He wears a zoot suit and his headquarters is a basement Italian restaurant. Instead of merely dressing up like the Tooth Fairy and procuring the money, he has an entire assembly line of employees who procure the teeth and inspect them for quality. When the boys attempt to break off into their own independent syndicate, Loogie intervenes and targets Kenny to teach them a lesson (which is a spoof on common Mafia practices). He is voiced primarily by Richard Belzer, although the final recordings were performed by Trey Parker. He made another cameo appearance in "Professor Chaos", where he was one of twenty candidates to replace the then-deceased Kenny in the boys' group. He survived the first round to become a semi-finalist but was one of four boys cut in the second round. In this episode, when his name was called out to advance to the next round, he was referred to as "Luigi".
To date, the show has not specified whether the character's name is actually Loogie, such that the "Luigi" reference is a "nod" or "nonce usage", or whether instead his given name is Luigi and the appellation "Loogie" is a (likely pejorative) nickname.
Read more about this topic: List Of Recurring South Park Characters