Jack Masterson is a character created in the spring of 2006 and voiced by Carlito. He is an obese, wheelchair bound Caucasian-American and is one of the most requested voices on the Madhouse Show. He is voiced by inserting a sharpie, cigar tube or other similarly sized object in the mouth between the gum and left cheek while breathing heavily directly into the phone. The voice has brought disgust to many female prank victims and has led to men inquiring if Jack is masturbating on several occasions. Masterson has also claimed to have been shot by a female sniper during the Vietnam War in the pancreas, causing him to develop diabetes.
Most of Jack's calls involve him making excessive requests upon businesses he plans on visiting on account of his large size and health concerns.
Origins
Masterson is based on Fingers the Clown whom Carlito witnessed entertaining children at an all-you-can-eat Chinese buffet in Daytona Beach, FL. Fingers sat in a wheelchair at the end of the buffet line and was sweating and breathing heavily while making balloon animals and performing tricks with large brass rings. He was also witnessed peeling and eating shrimp directly from the buffet line, discarding the shells and tails into a wrinkled grocery bag tied to his chair.
Parts of the Masterson character are also influenced by Roland Schwinn from the Phil Hendrie Show.
Health
Masterson originally claimed to weigh in at 535 lbs. Several weeks later he announced he had dropped down to 482 lbs, a benchmark he has yet to improve upon in the almost 2 years since.
Jack claims to be afflicted with type 3 diabetes ever since he was shot by a sniper in Vietnam. There is no such affliction as type 3 diabetes…only types 1 and 2.
Masterson has claimed to be near-death on many occasions (sometimes being given only 48 hours left to live) and has been advised by his doctors to prepare to pass away painfully and to get his affairs in order. Remarkably he has bounced back every time.
Trivia
Jack was originally named John Masters. Milkman accidentally referred to him as Jack Masterson and the name has stuck ever since.