A joke should catch someone by surprise, it should never pander.
–Norm Macdonald
Norm Macdonald turned awkwardness into a comedic art form. He was the master of making light of horrible scenarios with a brilliantly dry, ridiculously direct but silly, uncompromised style of comedy that was truly special. His innate ability to tell endless “Dad” jokes with insane verbosity, filling minute long gaps in between the premise and punchline with whatever happened to be floating around in his mind that very moment and then would somehow make it hysterical. And god-forbid anyone who rubbed him the wrong way as they would face the unrelenting wrath of his sharp-tongue. Favorite targets included the Clintons, Michael Jackson, Frank Stallone and of course, a one Orenthal James Simpson.
His ascension in the nineties on SNL was highlighted by spot on impressions of Burt Reynolds, Larry King, Bob Dole as well as the three-and-a-half-year stint he spent at the legendary Weekend Update desk. After constantly bashing the close friend of the network’s president, he was finally fired for dropping a F-bomb on the air, at his tape recorder for not cooperating with his front jacket pocket. I saw all this happen live and my laughter was quickly replaced with the realization that he was probably in deep shit for this one. Fast forward years later and he’s hosting the show and making fun of the very incident.
After everything that happened with SNL, he went on to write and star in some priceless, cheaply made comedic gems with great lines and scenes that still resonate today. Dirty Work and Screwed are both film’s we all collectively are thrilled to see randomly come on tv when home sick with the flu. Norm somehow combined stupid and witty into some bizarre fusion of direct, blatantly goofy but smart humor. His incredible improv abilities combined with his affable and dry persona evolved into him being the “Ultimate Late-Night Guest.” No one could top his comeback abilities which were challenged, time and time again by the eminent king of all wise-asses, Conan O’Brien.
The special relationship he shared with Conan started at SNL and culminated in numerous legendary interviews/interruptions on his late-shows through the years with some of the dumbest-smartest, most original comedy of all time. The Courtney Thorne-Smith/Carrot-Top incident was the pinnacle. Never was he so on, simply due to competing with his friend for the attention of a cute girl. What followed was beyond good talk show banter, it was witnessing an artist paint his masterpiece without even trying, to the point his opponent was crying with laughter because there was no sense in competing anymore with that kind of improvisational brilliance.
As I watch these old clips it is virtually impossible to contain my audible laughter which is synchronized with his sudden, way-to-honest and direct rhythm. These seemingly harmless jokes he told that started with a family themed setup were quickly reduced to some of the greatest, most well-crafted, articulate dick jokes that will transcend the ages… because Norm Macdonald had the balls to tell them.
The Modern Renaissance Man 
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