Earlier this week Dustin showed you guys a clip of a Craig Kilborn interviewing Jon Stewart on the old version of The Daily Show. The banter between an irritable Stewart and Kilborn was about as uncomfortable as late night talk show guest segments get, but it also had me asking myself “What the hell happened to Craig Kilborn?” It’s not the first time the thought had crossed my — or anyone’s — mind. It’s virtually impossible to stumble across one of his old clips and not ask the question.
Kilborn’s jabs that served him so well as an anchor on SportsCenter didn’t always help him build the best rapport with his guests. (One of my favorite guest segments involved Paris Hilton telling him about her new purse line and Kilborn cutting her off to ask his producer if the musical guest was ready yet.) He always kind of reminded me of an 80s teen comedy villain who had transitioned from captain of the varsity team to late night talk show host. I liked him on The Daily Show and then The Late Late Show, but wouldn’t let him give my girlfriend a ski lesson.
Kilborn’s Daily Show was a vastly different program than the brand that Jon Stewart has created. Kilborn preferred to give us more of a satirical take on the structure of the news while mixing in oddball segments like his famous “Five Questions,” something that he would take to The Late Late Show. He hosted The Late Late Show for five years before telling CBS that he was quitting and pursuing an acting career in 2004. Since then Kilborn has remained largely out of the public eye, or at least absent from our TV sets. What happened to Craig Kilborn? Will we ever get another Five Questions or game of Yambo? I want answers. To the internets!
The Shaggy Dog and The Benchwarmers
It’s 2005 and Craig Kilborn has just left his coveted late night CBS talk show, now all he has to do his kick his feet up and wait for those script offers to start sliding across his desk. And that script would be 2006’s The Shaggy Dog, a Disney remake about a lawyer who transforms into a dog starring Tim Allen. Nobody wants to be in a Tim Allen movie, not even Tim Allen. It probably wasn’t the movie Kilby hoped would kick-off his acting career, but it did also have Robert Downey Jr. in it, so who knows?
That same year Kilborn appeared in The Benchwarmers, you remember the Benchwarmers, right? That movie that you occasionally see on Comedy Central at 2 a.m. starring David Spade, Rob Schneider, and Jon Heder. The movie was a pretty forgettable Happy Madison production, but Kilborn does nail it as a the douchey former jock. Plus, it gave him an opportunity to work with Jon Lovitz, so it’s completely understandable why he took the role.
The Kilborn File — 2010
Between 2006 and 2010 it’s relatively unknown what Craig Kilborn was up to, he had a small role in a teen comedy called Full of It that also starred Kate Mara, but that’s about it. Oh, there was an Onion article on him in 2007, but my intuition tells me Kilborn likely had nothing to do with that. EW caught up with Kilborn in 2010, and were also curious what he had been up to for the last few years and why he had left his talk show.
Why did you leave The Late Late Show? “I accomplished my career goals and it wasn’t all it was cracked up to be. The format was repetitive. And there is a dysfunction to Hollywood. I pride myself on being down-to-earth. I’m from the Midwest. People who go into show business are screwed up. I romanticized about having a serene life. ”
I think people will assume there is more to the story than that.
“That’s the joy of life. No one has to believe anything.”
What else did you do during your time away? Describe an average Monday.
“Read the papers online. Listen to the local jazz station. Turner Classic Movies — I’m obsessed with Hitchcock. I like to make pulled pork, but it’s not healthy, so I make fish stew. And I drink moderately priced red wine. Is $70 a bottle moderately priced? I’ve lost touch.”
You can’t fault a man for wanting to enjoy a Hitchcock movie and that actually sounds like a pretty enjoyable Monday.
Kilborn was ready to get back behind the talk show desk in 2010 and was posed for a comeback with the The Kilborn File, a new talk show that would air at dinner time and featured Christine Lakin — better known as “Al” from Step-by-Step — as his sidekick. The show featured some of Kilborn’s trademark segments like 5 Questions and Yambo, but only ran on select Fox stations for six weeks before getting the ax. Monologue jokes apparently don’t have the same appeal at 6 p.m. as they do at 12:30 a.m.