The Letterman Years: Stories From Behind the Scenes of the Show That Changed Comedy Forever

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Where comedians of the first comedy boom dreamed of being Johnny Carson, the second comedy boom's late-night hosts — Jimmy Kimmel, Jimmy Fallon, Seth Meyers — all grew up looking up to David Letterman. “We're all 100 percent guilty of stealing from Letterman,” Kimmel told Rolling Stone for its 2011 feature, “How Letterman Reinvented TV.” “That show changed everything, and it changed the humor of the United States more than anything I can think of." Letterman strolled in like the Eliot Ness of television — suddenly, there was an expectation that you had to raise your game or be called out on it. "When Letterman was on, I thought, 'I know these people and this sense of humor – this is a world I have to find a way into,'” Judd Apatow told Rolling Stone of his subversive, conversational style. “There were six or seven people or groups who changed comedy in the Seventies and Eighties — Saturday Night Live, Monty Python, National Lampoon, Richard Pryor and Steve Martin — and Letterman is at the top of that list."

Before he ends his incredible run on May 20, longtime Late Show writer Tom Ruprecht shares a few funny stories with Vulture from behind the scenes of the groundbreaking show.

Prank Call, early ’80s
At NBC, Dave did a segment called “Brush With Greatness,” in which audience members shared encounters they had had with celebrities. On one particular show, a guy told a tale about being in a bar with his girlfriend, going to the bathroom, and returning to find her exiting with Jeff Conaway [the late Taxi actor and Celebrity Rehab participant]. After the show, Late Night received two messages. One from the guilt-ridden audience member confessing the story never happened (he just wanted to get on TV). Oddly enough, the show also got a call from a guilt-ridden Conaway asking for the audience member’s phone number. Conaway said he’d done some things in his life he wasn’t proud of, and he wanted to apologize.

The Delivery, summer of 1991
I was a receptionist at Late Night during the dark days after NBC had selected Jay Leno instead of Dave to host The Tonight Show. Warren Littlefield was the NBC executive largely responsible for making the choice, and now he wanted to fix his relationship with Dave. Warren’s idea was to send Dave a giant photo of himself. Apparently, in Warren’s brain, this constituted a “joke.” (I will say it does perfectly demonstrate the level of humor of someone who’d pick Jay Leno over David Letterman.) Anyway, the producers at Late Night got word that this giant photo was coming. I was given instructions to turn it away when it got to lobby security. The producers didn’t even want it to make it up to the 14th floor, where our offices were. Several days went by with no package. As a result, the looming threat of this photo slipped from the forefront of my mind. Days later, I got a call from lobby security saying we had a delivery. There were several deliveries a day.

“What is it?” I asked.

“A door.”

“Like a door door?”

“Yeah, a new door.”

It was not inconceivable that somebody on staff had busted their door and needed a replacement. It was a comedy show, people were always screwing around. For all I knew, somebody may have taken an ax to their door re-creating Nicholson’s “Here’s Johnny” in The Shining. (Carson was in the news, after all.) “Okay, send it up.” A messenger brought it up, and I immediately saw it wasn’t a door. It was a thick, wooden crate the size of an enormous poster. The size of a Warren Littlefield poster! Sure enough, the return address was NBC, Burbank, California.

“Please take it back downstairs,” I said.

“Nah, man. I don’t do pickups,” replied the messenger. We then proceeded to have a Seinfeld-ian conversation about whether it officially constitutes a pickup if I have not officially accepted the package. I lost. The guy just walked out, leaving the crate.

This was a disaster. I’d inadvertently accepted the gift. I was like a dingbat receptionist in ancient Troy who let in the Trojan horse. I called the NBC mailroom and told they needed to come pick up a package immediately. It was an emergency. It took them several hours. And during those hours, everybody on staff walked through the reception area. I stood in front of the mammoth crate, casually stretching my arms in a feeble attempt to block it. But it was no use. Everybody knew what it was.

There were a few people at Letterman over the years who didn’t seem to have much of a job description other than walking around looking for staffers to yell at. These people were the showbiz equivalent of hockey goons. Two of the goons descended on me and unloaded. They told me I was an idiot. That I’d fucked up big-time. They even insinuated that my career in television was over. All because I said “Yes” to a free door. It was an early lesson in the stupidity of TV higher-ups. I do want to say, David Letterman (the only guy who had an actual reason to be angry) was not one of them. He was completely cool about it.

Willie Nelson's Magic Bus, August 15, 1995
Talk shows all have the same basic guest lineup — big actor, mediocre actor, and then a music performance. Dave is one of the funniest people who has ever lived, and there’s nothing better than when he gets on a roll. When that occurs, however, the show goes long, and they have to bump one of the guests. Obviously, they’re not going to bump the lead guest, and the show can’t bump the band, because it costs a lot of money to bring them and the equipment back. So it’s the mid-level guest who goes. One day, we had to bump our middle guest — former thirtysomething actress Melanie Mayron. The musician that night was Willie Nelson. (You’re never ever gonna bump Willie because you don’t want to miss out on whatever weed he’s holding.) Well, on this particular day, there was a new stage manager filling in. The show was running long, so the decision was made that Mayron had to be bumped. In Late Show slang, when a guest is bumped, they’re “on the bus.” Word went out to the stage manager’s headset, “Melanie Mayron’s on the bus.” Now, as you may know, Willie has an infamous tour bus where much of the aforementioned weed is smoked. The bus was parked outside the theater on 53rd Street. So this poor, confused stage manager raced up the stairs, grabbed Mayron, and said, “We gotta get you on that bus!” He rushed her outside and shoved her onto Willie Nelson’s Acapulco Gold-laden vehicle. He then proudly reported to the Control Room that Mayron was securely on Willie Nelson’s bus. Our director said, “What?! Well, get her the hell off the bus!” So the stage manager ran back on the bus, grabbed Mayron, and hustled her off. I still remember her coming off looking dazed and confused (for more reasons than one). While she had only spent about four minutes on the bus, it looked like she’d endured four months in Amsterdam. Willie Nelson has been back on Late Show many, many times. The lesson, celebrities? It’s the considerate guests who bring pot that always get invited back.

Al Gore Has to Pee, September 14, 2000
Al Gore had to go to the bathroom, which I guess right there should have put a rest to all that “Gore is a robot” talk. Gore was running for president. GORE equaled ROBOT in the late-night calculus of the time. This was before Gore lost the election, grew a beard, hosted SNL, and everyone said, “Wow, if only he’d shown this side of himself, he would’ve won.” You know, the same thing people said about Mitt Romney after seeing the documentary Mitt. The same thing people said about Bob Dole after he made some self-deprecating jokes in the wake of losing in 1996. The same thing people said about … well, I guess no one ever said it about John Kerry. Anyway, Gore had spent the afternoon taping an interview segment on the Late Show rather than shaking a few hundred hands in Broward County, Florida. After the interview, Gore was being whisked off to his next event when he told aides he had to go to the bathroom. There is a bathroom in the basement of the Ed Sullivan Theater, so the Secret Service agents marched Vice-President Gore down the stairs. They flung open the bathroom door and one of the agents immediately recoiled in horror. Sitting on the toilet was Late Show regular Calvert DeForest (Larry “Bud” Melman to NBC viewers). Poor Calvert frantically waved his arms and legs while screaming, “Occupied! Occupied!” at the horrified vice-president. Despite all that was to happen a month and a half later, there’s not a doubt in my mind that seeing Calvert on the toilet was the worst thing to happen to Al Gore in the fall of 2000.

Steven Tyler's Tantrum, January 28, 2001
I was in Tampa shooting a field piece in which Late Show stage manager Biff Henderson talked to fans and celebrities at Super Bowl XXXV. Aerosmith was performing with ’N Sync at halftime, so during the first half, we made our way over to the dressing room to shoot a quick segment with Steven Tyler. I forget the joke I wanted Tyler to do, but I do remember it was something at the expense of ’N Sync. When I pitched the joke to him, Tyler got really angry. He told me ’N Sync were musicians and asked, “How dare I make fun of any artist?” That’s a completely valid opinion, so I suggested we do a different joke that had nothing to do with ’N Sync. As I described joke No. 2, Tyler pleasantly asked, “Wait, what happened to the other joke?”

“The ’N Sync joke?” I asked cautiously. “I got the impression you didn’t want to do it.”

“No, man. I’ll do it,” a suddenly mellow Tyler assured me.

Okay, great. So I brought in Biff and began to explain how the joke would work. When I got to the point of the joke that mentioned ’N Sync, Tyler again exploded.

“I told you I don’t want to do that joke!” he screamed.

“Right, but then you said— ”

“Oh, I see what’s going on,” he shouted, “You’re trying to trick me.”

I tried to go back to idea No. 2, but Tyler wouldn’t have it. He was furious at me for trying to get him to do a joke he specifically said he didn’t want to do, and ordered me to leave. Part of me was hoping Tyler would point to the door and sing, “Walk that way,” but alas, no. Even as I left, Tyler continued screaming at me. For the life of me, I can’t understand what could have possibly caused a ’70s-era rock star to behave so erratically. I guess we’ll just never know. Pre-show jitters, maybe.

Paul Newman Loses His Cool, 2001 Detroit Grand Prix
We shot a field piece at the 2001 Detroit Grand Prix in which Biff went around talking to drivers and fans. Paul Newman and Ashley Judd, both huge race fans, were there, and kindly agreed to appear in the piece. So we sat with them at a picnic table discussing what we should shoot. Ms. Judd looked beautiful, but that did not stop her from twirling around in front of us and asking, “I don’t know, does this outfit make my butt look too big?” (Spoiler alert: It didn’t.) As she showed us her butt, I glanced over at Paul Newman, who was gnawing on the tablecloth as he ogled her. Yes, he was literally chewing the tablecloth, looking for all the world like a horny 16-year-old boy. Our director Jerry Foley turned to me and said, “If Paul Newman at age 76 still hasn’t scratched the itch, what hope do any of us have?”

Russell Simmons's Meltdown, 2004 Democratic Convention
I shot dozens and dozens of field pieces over the years at Super Bowls, World Series, the Olympics, and so on. Yet despite dealing with hundreds of celebrities at high-stress events, the only one other than Steven Tyler who was “challenging” was Russell Simmons. It was at the 2004 Democratic convention in Boston. I didn’t initially approach Simmons to be in the piece. I assumed he was there to advocate a political cause and wouldn’t be interested in doing comedy. It was Simmons’s people, however, who let us know that he really wanted to be in the segment. Some celebrities merely tolerate being in these comedy pieces, so if you have one who actually wants to play along, you’ve hit the jackpot. I picked a very easy joke to start — Biff would ask if he was in favor of gay marriage. Simmons would answer, and then Biff would have a prepared joke. It didn’t matter how Russell answered, so long as it was quick for sake of the joke’s timing. I explained that he only needed to say “Yes” or “No.”

We started rolling, Biff asked him if he was in favor of gay marriage, and Russell said, “Well, Biff, it’s a complicated issue …” He proceeded to ramble on for a few minutes.

When he finally finished, I said, “Okay, we have that version, now let’s do one where you just give a one-word answer and then Biff will have a line.”

Biff re-asked the question, Russell took a deep breath and began to orate, “Well Biff, it’s a complicated issue …” Again he went on for several minutes. The remote itself was only going to be about two minutes long, so this was clearly not going to work. I said, “Okay. Let’s do one more and this time, it literally is as simple as you saying, ‘Yes’ or ‘No.’” Russell glared at me. "Man, are there any serious questions? I don't want to be a clown."

Point of order, “Are you in favor of gay marriage?” is a serious question. But I had lots of jokes, so finding him a new one wasn’t a problem. I scanned my pad for an alternate.

“Gimme that,” Simmons said grabbing at my pad. I pulled it away from him because there were lots of jokes — some meant for politicians, some meant for women, some meant for delegates, some meant for celebrities. At a glance I could dismiss the ones that wouldn’t work for Russell Simmons and instead find a few choices that were right for him. It didn’t make sense to have him read through everything to select a joke. He demanded to see the pad. I told him, “No.”

“Lemme see it or I’m not gonna be in this piece.”

It was obvious this interview wasn’t working, so pulling the plug was actually the logical solution. I said, “Fine,” and motioned to the crew that we were done. I started to head off.

Simmons said, “YOU’RE A DICK!” I turned around. Did I hear that right?  He proceeded to call me “dick” a few more times. People around us stopped what they were doing and stared. It turns out one of the people was from Newsweek, and an article was soon on their site, stating:

Simmons demanded to see the questions on the producer's yellow pad. When the producer demurred, Simmons canceled the interview. "He must have rubbed Simmons the wrong way," an Associated Press photographer said of the exchange, because before the press could get their tape recorders out, the hip-hop mogul calmly but loudly and repeatedly told the producer, on the floor of the Democratic National Convention: "You are a d*ck. You are a d*ck."

When the article hit Newsweek, it was Biff’s turn to get inexplicably annoyed with me. Biff was mad that I had now involved him in a scandal. A scandal, as if this was Chappaquiddick or something. So, I’m sorry, Biff. I’m sorry Russell Simmons repeatedly called me a “dick.”

Clinton & Chewbacca, 2009-2010
Bill Clinton was hanging out near my wife, which is something no husband wants. My wife also worked at the show, and the former president was backstage watching the Top 10 List while awaiting his guest segment. I had a joke in the Top 10 that mentioned Chewbacca. The joke got a pretty big laugh backstage, but Clinton seemed confused. He turned and with a quizzical look asked, “Who’s Chewbacca?”

First off, I have to admit that having written something that prompted Bill Clinton to say the word Chewbacca stands as the proudest achievement of my life. (I’m the father of two.) My next goal is getting Pope Francis to say “Wu-Tang Clan.” But the more I thought about it, the madder I got. Yes, Bill Clinton’s a world leader with lots of important things on his mind. We get it. But when Star Wars came out in 1977, Clinton wasn’t the president. He was a regular guy. Heck, his nickname was “Bubba.” A guy named “Bubba” can’t pretend he’s too important to know who Chewbacca is. And also, isn’t Clinton always claiming to be a New York Times crossword-puzzle expert? Chewbacca is exactly the kind of random reference any decent crossword-puzzler would be aware of.

50 Ways to Howl, October 2013
Yoko Ono performed a song on the show in October 2013. There were a few points in the song where Yoko was to “HOWL.” While most of us only have one way of howling, Yoko apparently has a vast array of howls in her repertoire. She wrote notes next to the HOWL to remind herself which specific Howl to use. The first HOWL had the reminder, “Like a dying bird.” The second HOWL had the notation, “Like a confused chipmunk.” The third HOWL, “Like a bird on its last breath w/ a chipmunk in its mouth.”

As he does his final show, that’s kinda how I hope to see Letterman go out. Howling like a bird on its last breath w/ a chipmunk in his mouth.

Tom Ruprecht is a writer at The Nightly Show With Larry Wilmore. He’ll have an article about funny things that happened on that show some time in the year 2035. Follow him @truprecht.