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Jonathan Gregory: The Creepiest Comedian In America

Jonathan Gregory just being Jonathan Gregory. (AP Photo/Dennis System)

Jonathan Gregory just being Jonathan Gregory. (AP Photo/Dennis System)

Phoenix, AZ — Sitting in the front row during a comedy set with Jonathan Gregory is about the worst possible thing you could ever do in life. This guy knows how to work a room; picking out the weakest link and then devouring them with his hard-hitting, extremely uncomfortable, serial-killer-ish, style of humor. Nothing is off limits to Gregory.

I remember being at a party about a year ago with Jonathan. He walked up to me without saying a word. He then proceeded to look me directly in the eyes for what seemed like an eternity, then took his attention off me and gradually looked around the room, eying each person there. Then Gregory turns back to me and in a deep voice slowly says, “Which one would you kill first?”

With his signature black shirt, long hair and menacing facial expressions, this dude is creepy and it all adds to the fun of his act.

Jonathan Gregory working the crowd. (AP Photo/Dennis System)

Jonathan Gregory working the crowd. (AP Photo/Dennis System)

Gregory’s comedy, although unique and different, has been well received by a wide variety of audiences. This includes bars, theaters, world-class comedy clubs and even retirement homes. Gregory has over 10 million views on his YouTube page and his television credits include Showtime Boxing, NBC’s Last Comic Standing season 6, and E! Network’s True Hollywood Stories Investigates Hazing.

According to Gregory’s website, he spent over a year on a weekly morning radio program called “Think Tank Tuesday” which was part of the Morning Infidelity on KWSS 106.7FM. There his awkward take on the daily news brought laughter to listeners as they went about their morning commute. Gregory’s stand-up has been featured at the SLO Comedy Festival, Ventura Comedy Festival, the iO West Comedy Festival in Hollywood, Comedy Central’s “Up Next” Contest, Rooftop Comedy, and he was named Arizona’s best comedic writer by judges at the Tempe Improv.

So what is in store next for Jonathan Gregory? Well, I suppose that is the million dollar question. My guess: Prison or Conan.

VIDEO: The Comedy of Jonathan Gregory


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About the author

Jimmy Rustling

Born at an early age, Jimmy Rustling has found solace and comfort knowing that his humble actions have made this multiverse a better place for every man, woman and child ever known to exist. Dr. Jimmy Rustling has won many awards for excellence in writing including fourteen Peabody awards and a handful of Pulitzer Prizes. When Jimmies are not being Rustled the kind Dr. enjoys being an amazing husband to his beautiful, soulmate; Anastasia, a Russian mail order bride of almost 2 months. Dr. Rustling also spends 12-15 hours each day teaching their adopted 8-year-old Syrian refugee daughter how to read and write.