“You take away the suits and the noise on these shows, and you’re left with just the person. That’s something that shows Stephen in a really good light.” ~Late-night veteran Conan O’Brien in “Variety” magazine

For my money, Stephen Colbert is one of the great political satirists of our time. From 2005 to 2014, Colbert was the host of Comedy Central’s The Colbert Report in which he portrayed a conservative political pundit. I first met Stephen at a “Stand Up for Heroes” charity event sponsored by The Bob Woodruff Foundation (see his WINNER profile) in November 2007. We met again at the 2008 Emmy Awards both on the Red Carpet beforehand, and at the Governor’s Ball afterward. The latter encounter was memorialized in a photo taken outside a bathroom where I had held Stephen’s first-ever Emmy. As you’ll learn in the paragraphs to follow, that photo would gain some notoriety a few years later.

In 2011, Colbert established the Colbert PAC (a so-called “Super PAC”), and it produced ads asking voters in the Iowa Republican Straw Poll to write in Texas Governor Rick Perry’s name. The problem: the Colbert PAC ads encouraged voters to misspell the name as “Parry” with the “A for America.” While my instincts have always been to err on the side of caution in such matters and grant access to qualified parties, we declined to accept the ads in this case on grounds that their purpose was to cause confusion. As funny as the ads were, I didn’t want my station to aid and abet its clearly intended mischief. Interestingly enough, two other television stations in Des Moines did accept the ads – and take the Colbert PAC’s money – as was their prerogative. David Oxenford, a respected communications lawyer, would later write the following in a blog posting: “The station was not only within its rights to reject the ads, but had an even greater responsibility to vet the third-party ads since stations are theoretically responsible for the content in those ads.”

Well, it was obvious that Stephen didn’t buy our reasons for the rejection when he absolutely lampooned us off the top of his show on August 11, 2011. He personally dared me to “touch his Emmy” after pulling it out as a prop near the end of his rant. The next day I called Stephen to remind him that I had, in point of fact, touched his Emmy! It made for a light conversation and we shared a great laugh. Then on August 15, 2011, Stephen opened his show with “a rare apology” and went on to say this: “(Ray Cole) has touched my Emmy, and when you’ve touched my Emmy you have touched the very best part of me.” Stephen later included the station’s news team in a follow-up bit on August 18, 2011.

Stephen moved on from The Colbert Report to succeed David Letterman as host of The Late Show on CBS. It quickly became the highest-rated late-night talk show, a ranking held for nine consecutive seasons. In a controversial move, CBS announced in July 2025 that The Late Show would end in May 2026. The network claimed the move was a “purely financial decision” but skeptics pointed to the decision’s close proximity of the timing to the merger of Skydance and Paramount. After all, the show was known for its frequent criticism of the Trump administration. The last episode of The Late Show aired on May 21, 2026. 

Stephen is a one-of-a-kind WINNER who went on to win eleven Primetime Emmy Awards — more than I could hold in almost any situation. And definitely more than I could ever hold at one time in a men’s room.

Stephen Colbert “apologizes’ to Ray Cole

Sources

Websites –

Romenesko, Jim (August 17, 2011). “WOI-TV: Colbert PAC ad rejection ‘a close call’” Retrieved from www.poynter.org

Eggerton, John (August 31, 2011). “WOI’s Super PAC Smackdown” Retrieved from www.broadcastingcable.com

Last Updated: October 26, 2024