Chestnut was born in Dallas, Texas in 1971. Perhaps that explains it.
Or, it could be that his family moved around a lot. Maybe there's a
repressed memory of a bad uncle. We don't know. But somewhere along the
way, he caught the comedy bug, and sought thereafter to be the best
damned comedian he could be.
reality, Randy Chestnut was talked into trying comedy by friend and
fellow comedian Dave Ing. After a long, arduous process of writing,
rewriting, brainstorming, refining, rehearsing, and memorizing, Randy
(along with Dave, as the two wrote material together during their early
years) came up with ten minutes of material he thought suitable for
public consumption. With confidence usually absent an amateur, he took
the stage at the Funny Business Comedy Club (now called The Comedy Club On State) in Madison, Wisconsin in early June of 1997.
And bombed. Well, comparatively speaking, anyway. Seriously. We have this on tape. We can't watch it without cringing.
will not stand, thought the ambitious young(ish) (would be)
comedian. He went back to the drawing board and wrote. And wrote. And
wrote. And practiced. And refined. You get the point.
At one point, he caught the eye of local celebrity Dave Gray,
and was given encouragement by him. Heartened, he continued to struggle
through a then-thriving local comedy scene, moving through the fiercely
competitive ranks. By 1999, he was rewarded by winning his first (and
only) comedy competition, and was named Funniest Person In Madison.
Chestnut later declined to participate in further competitions, finding
Also in 1999, Randy was invited to perform in the first of two Comedy Central™'s Comics Come Home™, for the benefit of the Chris Farley Foundation,
which raised awareness of drug and alcohol abuse. This was the early
highlight of Chestnut's career, and he was rewarded for a good set by
being invited back in 2000. Also in 1999, he also opened for jazz-funk
fusion band Phat Phunktion in front of 4,000 University of Wisconsin students. And bombed. So there was still work to do.
this time, Randy was touring as a professional comedian across the U.S.
In a comedy club gig in Rapids City, South Dakota, he met up with
comedian Mike Dambra.
Being a veteran of the Canadian comedy circuit, Dambra (after
relentlessly needling Randy) offered to take Randy on a tour of the
Canadian comedy-chain giant, Yuk Yuk's. Chestnut accepted, and had an
excellent time, punctuated often by more incessant ribbing by Dambra.
We mean this. The guy is unstoppable.
the intervening years, Randy Chestnut has grown as a performer, and so
has his territory. He now crisscrosses the nation, from the east to the
west coast, from Sault Sainte Marie, Michigan
to Little Rock, Arkansas, and all parts in between. Oddly, considering
he spent years living in Texas and Florida, he has never gone very far
south. We think he's afraid of starting a second Civil War.
2008, Randy took a hiatus from comedy in order to see to family
matters. He is now rested and ready to continue pushing the envelope in
every club on every stage in every state. See him if you get the
chance. We suggest you bring a dictionary.