Tales from the ‘Late Night with Conan O’Brien’ Writers Room

The Paley Center for Media, which has locations in both New York and LA, dedicates itself to the preservation of television and radio history. Inside their vast archives of more than 120,000 television shows, commercials, and radio programs, there are thousands of important and funny programs waiting to be rediscovered by comedy nerds like you and me. Each week, this column will highlight a new gem waiting for you at the Paley Library to quietly laugh at. (Seriously, it’s a library, so keep it down.)

The nice thing about the subject of today’s article is that I don’t have to start off with a bunch of context or explain to you why this particular show was important to comedy. If you’re on this website, then you probably already know that Late Night with Conan O’Brien was one of the funniest shows to grace television, and that it’s illustrious writers room has brought us so much great stuff over the years, beyond just Conan’s show. From Louie to Delocated to Mr. Show, some of the finest comedy writers sat in a room together making each other laugh (while getting picked on by their boss, Conan O’Brien. More on that later.).

On November 8th, 2008, The Paley Center got together six of the writers from the then current writing staff of Late Night, along with author Sarah Vowell to serve as moderator. On the panel that night was Dan Cronin (also a stand-up comic, who has continued on with Conan to The Tonight Show, and Conan on TBS), Berkley Johnson (now a writer on The New Girl), Brian McCann (who on Late Night played Preperation Harry, Fed-Ex Pope, and many others), Matt O’Brien (who stayed on with the move to LA and TBS), Brian Stack (who you might recognize as Frankenstein on Late Night, or Artie Kendall the crooning, racist ghost, or The Interrupter, or many others), Andrew Weinberg (co-creator of Eagleheart) and Mike Sweeney (head writer on Late Night, The Tonight Show, and Conan). Ms. Vowell interjects here and there, but for the most part just lets the writers run the show asking just a handful of questions. What follows is a collection of my favorite anecdotes from behind the scenes at Late Night.

Sarah starts the night by asking about the writers’ failures. Here we learn about the sketches that either bombed on stage or bombed so hard they were cut out of the show. This includes such characters as “They Guy With His Diddle Doobie Douche Machine” who would push a button that would play a recording of a someone saying “diddle,” “doobie,” or “douche” to match up with photos of Paris Hilton, Snoop Dogg, and George W. Bush. Or the retired office Tom Brokaw Impersonator, who, upon the retirement of Tom Brokaw from NBC, was hoisted up into the rafters of the Late Night set, only to dangle there as he watched Conan and the head writer deliberate for 15 minutes on cutting the bit from the show. Or my personal favorite aborted character mentioned in the discussion, Dan Danna: They Guy Whose Never Heard of Bandanas. Brian Stack talks about Louis C.K. writing a fake ad for the show’s “Actual Items” segment, in which an ad for Old Coins had the tagline: “Coins so old you can buy slaves with them.” Conan resisted the bit until Louis C.K. called him a “baby.” That night, without prompting, Conan was booed by the audience.

The writers talk a lot about what would happen if you were the one that wrote the thing that bombed. From the sounds of it, their boss really liked to tease his writers. Sweeney says that during the show if a particular bit died on stage, Conan would like to make eye contact with that writer and then remind them about it several times the next day. On the one hand, if a writer truly believed in an idea, Conan was open to them, and if their passion was strong enough, would put it on the air. On the other hand, if it bombed… well, Sweeney doesn’t say Conan would root against those particular pieces, but he does imitate the host rubbing his hands together maniacally like a movie serial villain who has just tied a woman to the train tracks.

According to the writers, though, the best thing about Conan is the fact that he was actually around the office. He was a presence there and would give feedback, listen to ideas and “come around with the guitar and sing songs about your weaknesses.” Brian Stack talks about Conan’s proclivity for generating metaphors for his staff that were perfectly insightful. For example, on a night where Brian was feeling nervous, Conan entered and asked him, “Stack, you know what you are? You’re one of those playwrights from the 1930s pacing around in his tuxedo, waiting for the morning papers to arrive.” Or the way that he would describe the look of another writer, Kevin Dorff, who had a classical Irish tough guy look, “Dorff, what are you doing here? Shouldn’t you be off throwing cabbages at Lincoln’s inaugural train?”

The writers also came ready to dish about some of the many celebrities that have taken part in the show’s bits over the years. For example, the “Celebrity Secrets” bit, in which a celebrity sits in an interrogation room set, reading joke “confessions” about their lives, always began with the celebrity pouring themselves a glass of water. Donald Trump decided to pour some water in his glass, then pour the rest of the pitcher on to the desk before proclaiming, “you didn’t think of that, did ya? I thought that was very funny. You gonna use that or not?” While doing the same bit, Gene Simmons read through the list of jokes and vetoed the majority of them because they had the names of other celebrities in them. “These people in the jokes can mention me, Gene Simmons, as many times as they want, but I’m not going to say their names. No free rides.”

While some of the faces have changed over the years, clearly life in the Late Night writers room was entertaining to say the least. While things do get a little awkward for present day viewers when the writers discuss what they think will make things different when Conan moves to the Tonight Show at 11:30, The entire panel is an entertaining behind the scenes look at how one of the funniest TV shows in recent memory was made.

Ramsey Ess is a freelance writer for television, the head writer of his website, a podcaster and a guy on Twitter.

Tales from the ‘Late Night with Conan O’Brien’ Writers […]