Daniel Kibblesmith was called the “Clown Prince of Groupon” in a profile published by New York Times Magazine in 2014. But ever since he answered a Craigslist post by Groupon’s founder, Andrew Mason, and editorial director, Aaron With, seeking a “freelance humor writer,” Kibblesmith’s rise to the comic stratosphere hasn’t been a joke.
And this year, in particular, the Oak Park and River Forest High School graduate has been on a roll. He’s up for two Emmys and in June, he was selected as one of four OPRF Tradition of Excellence award recipients, along with philanthropist Sarah Coglianese (Class of 1996), army officer Matthew Smith (Class of 1994) and state Rep. Camille Y. Lilly (Class of 1979).Â
Kibblesmith got the job at Groupon in 2009 after writing what he described for the Times as a “‘half-assed’ application that consisted of a series of zany, absurdist sketches.”Â
Such as this one:Â
“I remember there was one joke about a guy who was high out of his mind on some kind of substance, and he needed to have a conversation with his roommate’s dog, because he needed to be next to something that didn’t hate him,” Kibblesmith told the magazine.Â
For roughly five years, the OPRF graduate was the resident comedian at Groupon, the Chicago-based company that offers discounts on everything from oil changes to kayak rentals to energy supplements.Â
While at Groupon, Kibblesmith’s job title was senior marketing copywriter. In reality, that translated into overseeing the company’s slightly off kilter brand of humor that’s on full display in the many coupon and deal descriptions the company posts each day (“$100 for a Bedtime Tuck-in from Ben Kobold”).Â
In 2014, Kibblesmith left Groupon seemingly much richer than when he started—at least rich enough to fill in for Mason on Bravo’s “Millionaire Matchmaker.”Â
In 2015, he joined “The Late Show with Steven Colbert” as a staff writer. This year, he earned two Emmy nominations for Outstanding Writing for a Variety Series. He also published a book, Santa’s Husband, which, according to the Amazon description, offers “a fresh twist on Kris Kringle” and is “a clever yet heartfelt book that tells the story of a black Santa, his white husband, and their life in the North Pole.”
This year’s Tradition of Excellence winners were chosen by a committee that consisted of Regina Topf, OPRF’s director of student activities; Jonathan Adelman, a teaching assistant, coach and OPRF grad; student council co-sponsors Katie Prendergast Tilia Detrick; student council officers; and D200 Board President Jackie Moore.Â
An award reception for the honorees is scheduled for Nov. 10. Â
CONTACT: michael@oakpark.comÂ






