Comedian, writer, and producer Chuck Sklar’s late-night résumé spans four decades, with stops along the way at Politically Incorrect with Bill Maher, Late Night with Conan O’Brien, The Chris Rock Show, The Late Late Show, Lopez Tonight, and Totally Biased with W. Kamau Bell.
But if he could do it all over again, there’s one early job he wouldn’t have left: writing monologue jokes for Conan O’Brien.
“I’m an idiot,” Sklar tells Mark Malkoff on this week’s episode of LateNighter’s Inside Late Night podcast.
Sklar joined Late Night in 1993, just months into O’Brien’s run, and helped shape the show’s early monologue style, which favored runs of jokes on a single subject. He also made it on camera, performing stand-up three times and appearing as David Copperfield in recurring remotes after writer Mike Sweeney noticed their resemblance.
After two years, Sklar left, hoping to move beyond monologue writing and into sketches. Looking back, he says he would tell his 32-year-old self, “You’re not quitting this job.”
What he was looking for, he eventually found at The Chris Rock Show, where Sklar became a sketch writer and won an Emmy. He credits Bob Odenkirk with helping him get there after Odenkirk happened to run into Rock and offered an unsolicited endorsement.
“So I owe Odenkirk a lot,” Sklar says.
The irony is that monologue writing kept finding him. Sklar later reunited with Rock at Saturday Night Live in 2014, helping him whittle roughly a half-hour of club material into a few minutes for his hosting monologue.
Elsewhere in the conversation, Sklar discusses his brief stint with Bill Maher, working for Craig Kilborn and James Corden on The Late Late Show, Roseanne Barr’s short-lived Saturday Night Special, and eventually finding himself in charge of the monologue again on Lopez Tonight. “Somehow that’s my thing,” he jokes.
Click the embed above to listen to Mark Malkoff’s full conversation with Chuck Sklar now, or find Inside Late Night on Apple Podcasts, Spotify, or wherever you listen to podcasts.
