In his pay-per-view special, Leary told the story about how as a small boy he lived in a three-family house off of Main Street in Worcester. He used to walk to the corner of Main Street and push the "Walk" button, then run back down his street. The traffic would stop, then as the light would turn green, he would go back and repeatedly push the same button until traffic on Main Street was completely snarled. He said that one day, he was finally picked up and brought home by the cops. He was only four years old at the time. The way he told the story had the audience laughing so hard (he peppers his delivery with a lot of 4-letter words, etc., too).
When Leary was discussing his skating effort to support the firefighter fund, he discussed his fond memories of how he was introduced to skating at age four by being brought to Elm Park, and how he skated in a "pee-wee"-level hocky program for several years at a rink that used to be somewhere near Webster Square. Leary said that one time while at Elm Park, he became so cold that he told the audience, "I said to myself, 'F**k this, Why does anyone enjoy freezing their a** off to skate!!?"
Leary's street-level humor and his Worcester roots are a great combination, and his show is now on DVD.
