One fateful night in the summer of 1988, I took acid. Steve Jobs apparently said he’d never hire a CEO who hadn’t done it — but this wasn’t a career move for me. Looking back, I really had no idea what I was getting myself into; I was 24 years old and in my sixth year of struggling through NYU with the equally preposterous/pretentious notion that I was going to be a playwright.

I had spent the better part of those six years bartending at a popular blues bar on Bleecker Street (Mondo Cane) with a far more serious focus on getting drunk and laid than anything resembling academia. So one night, rather than study, I decided to drop some acid with some friends — and braced myself for a night filled with wonderful and colorful hallucinations. That happened, but at around 5 a.m. things took a sharp turn. I began a more sobering, melancholic, empathetic journey down memory lane. There was no fog or druggy haze. In fact, there was a clarity unlike any I’d ever known. There were my parents, loving and earnest … my siblings … my friends, past and present … and then there was me: What the fuck was I doing with my life?

As the sun began to rise, I sat down and wrote a contract with myself. I still have it. It’s titled “Contract With Myself.” I resolved to “stop chasing fucking miserable entertainments” and to “stop squandering opportunities.” At the end of writing it, I had another clear realization: I really had no business pretending to be a playwright. I resolved to get a real job. But then I had an equally ridiculous epiphany: I should work for David Letterman.

At that time, Dave was the hero to every college student in America. In this ’80s era of bloated egos, yellow power ties, and money over matter, Letterman did not give two fucks. And it wasn’t so much mean-spiritedness, as was frequently misinterpreted by people who had no idea what they were talking about: If you were a guest who was a normal human being, you were fine — he’d be curious and ask thoughtful questions. But if you had airs? There was nothing more fun to watch than Letterman effortlessly deflate people with inflated senses of worth (i.e., self-important celebrities). To watch it was like witnessing verbal sleight of hand.

So to me, it wasn’t really even about the iconic comedy stunts, like the Alka-Seltzer suits — though I frequently wonder how much bigger even he would have been had the Internet been around then — as much as it was the arch-browed skepticism with which he approached everything. For my generation, Dave was a modern-era folk hero without the corny aphorisms: He helped Americans tap into their inner cynicism at a time when it was in danger of being eclipsed by Reagan’s “Morning in America” propaganda.

Less than a month later, I met Matt Wickline at a party. He was a writer at Letterman. It was fate! I asked him about working there — maybe as an intern? He gave me the name of Kathy Michalcik (now Mavrikakis, but still a producer on the show) and said, “All our interns are lame. It shouldn’t be so hard for you to get.” And with that backhanded compliment, my career began.

Daniel Kellison

Sammy Davis Jr.

My first semester there was spent working for Madeleine Smithberg (who would go on to cocreate The Daily Show). At the time she was the Human Interest Talent Coordinator, finding the weirdos and the other non-celebrity guests for Dave. I’d spend my day going through stacks of local newspapers and cold-calling the local affiliates. I was thrilled to be a part of it, especially when I’d find someone who would get booked.

I was now “a part of the show” even if I wasn’t actually getting paid. But after my semester was up, there were no job openings. So my pal Donick Cary (most recently an executive producer at Parks and Recreation and New Girl) and I decided to ask if we could stay another semester. They agreed. But after that semester passed, there were still no openings. Dejectedly, I returned to my bartending job.

Within two weeks of leaving, I heard that a talent researcher job opened. I was warned that there would be many applicants — it was not an entry-level position. But the good news was that it would be a level playing field: The show would call us on Friday, tell us whom we had to research — and then we’d all have to turn in our research packets and profiles Monday morning, with the notion that whoever submitted the best packet would get the coveted post.

The call came. The person we’d be profiling was an upcoming guest … Sammy Davis Jr. Good god. As this was before the Internet, I quickly beelined to the New York Public Library to begin my research — I knew countless other applicants would be doing the same. Alas, Sammy had not one, not two, but three autobiographies (Yes I Can, Hollywood in a Suitcase, and Why Me?) — which ran over 1,200 combined pages. I checked them all out and began reading.

My biggest takeaway — and what I planned to focus on to make my profile stand out in the blur of 80-plus others they’d be reading — was the side of Sammy the sexual explorer. About halfway through Yes I Can, he began talking about his “friendship” with Linda Lovelace (of Deep Throat fame) and her horrible husband Chuck. Sammy also mentioned offhandedly that he was the best man at their wedding. I surmised — correctly — that there was probably more to that story.

So I called around and found a feminist/Wiccan bookstore in the West Village that happened to carry Linda’s autobiography Ordeal — and, as luck would have it, had one copy left. I highly recommend the parts about Sammy. It was a veritable gold mine featuring the freewheeling, coke-snorting Candy Man, his pal Hugh Hefner, some good-old fashioned bisexuality, and a light smattering of bestiality — because apparently there was no better way to tackle sexual boredom in the ’70s than by mixing in farm animals.

I prefaced my Sammy profile by saying, “I know you can’t use this for air, but I’m including this for overview …” and then jumped in. I had all the horrible Lovelace stuff — but then there was so much more. Like about Sammy “cleaning up the Pussycat Theater” and then bringing Lucille Ball to see Deep Throat. I loved that. I started thinking this would be a fun job, and that maybe I stood a shot.

A week later, the show’s executive producer, Robert “Morty” Morton, called. “Danny,” he said, “we still have to read a few more, but I wanted to call you personally and tell you I thought you did an amazing job — you definitely had stuff no one else had, and your profile was really entertaining.” There was definitely a “But” looming. “But … we’re probably going to give the job to a researcher from the Today Show. He has practical experience you don’t, and has been trying to work for us for five or six years.” Quietly devastated, I said I understood and hung up.

The next day I wrote Morty a letter. In hindsight, it was overly-aggressive-bordering-on-dicky, but I had nothing to lose. I said, “Which would you rather have — some old, tired researcher who’s been doing the same thing for years and hasn’t ever been promoted — or someone young and hungry who is going to kill himself every day to prove himself to you and Dave?”

A few days later, at about 1 p.m., the phone rang. I was sound asleep (I usually closed the bar around 5 a.m., and would frequently go out for something to eat after that). Hungover, I mustered up a groggy “Hello?” Morty asked if I was asleep. I acknowledged that I was. He said, “I was going to offer you the job — but now I’m not so sure.” I snapped to — “No, no! I want it! I want it!” He laughed. “OK, see you Monday. You got it.”

The “Potatoe” Kid

In choosing his running mate in 1988, George H.W. Bush inadvertently bestowed on the country one of the greatest late-night comedy offerings of all time: the dunderheaded Dan Quayle. And in selecting Quayle, Bush simultaneously — some might even say savvily — secured the greatest assassination insurance policy a president has ever had. I say this with obvious prejudice, because there can be no other explanation as to why he kept Quayle on the ticket when he sought reelection four years later.

The chickens came home to roost during a momentous reelection campaign stop in New Jersey. As if out of some wildly implausible episode of Veep, Quayle’s advance team decided it would be a good idea for him to stump at a spelling bee at Muñoz Rivera Elementary School in Trenton, New Jersey. What could go wrong? Right? As you can see below, after 12-year-old student William Figueroa wrote out the word “potato” on the board, Quayle somewhat smugly “corrected” William, having him add an “e” to the end of it.

Immediately, Figueroa became the big get among all the late-night and morning shows. Since William was 12 and overwhelmed, he and his family did what any normal family would (and should) do: closed the doors, shut the shades, and hoped the press would go away. But as we know, the press is never that easily discouraged — instead, they camped out. Knowing I would never succeed in that scrum, I decided to send a pizza with my phone number inside. I certainly can’t take credit for inventing this sneaky maneuver (this is something of a time-cherished talk-show chestnut), but it worked. William’s dad called, and soon we had William locked as an exclusive guest. At the time, I was still a talent researcher, in charge of digging through old articles looking for possible topics the guests could talk about with Dave. But as a reward for booking Figueroa, I was told I could produce his segment myself.

The most challenging and fun part of producing a segment was writing a guest intro that Dave would use; he preferred them to be short, funny, and punchy. For William I wrote, “Yesterday, our next guest walked up to a chalkboard. The events which followed terrified a nation.” The next day, Dave’s interview with young William was on the front page of all the New York papers; there was even an editorial in the Daily News about Quayle with the headline “Terrifying a Nation.”

Drew Barrymore

In 1992, when Dave moved from NBC to CBS, I was promoted to segment producer. The guests would be divided up between me and Mary Connelly (who is currently executive producer of Ellen). Our jobs were to pre-interview the guests to figure out topics they’d discuss with Dave and to plan any other bits they could do. In 1995, I was paired with Drew Barrymore, with whom I’d worked before on the show and who was one of my — and Dave’s — favorite guests. We had booked her, coincidentally, for Dave’s birthday. A night or two before we were scheduled to talk for her pre-interview, she had gone to a semi-famous hipster underground cabaret in Tribeca called the Blue Angel. Being a free spirit, Drew had decided to spontaneously take off all of her clothes for the small audience. This was well before TMZ, cell-phone cameras, and the omnipresence of the paparazzi, but it still became a pretty big story and made the cover of the next day’s New York Post.

As far as I knew, we’d be the first ones talking to her since the incident — if she didn’t cancel (which was generally a celebrity’s M.O. after any controversy preceding an appearance). But Drew honored the booking. She called right on time and was as ebullient as always: “Dan, it was soooo liberating. You have no idea, to be naked up there in front of all those people!” I told her that I had once tried — very unsuccessfully — to get Letterman to check it out with me. (Interestingly, the night I went, there had actually been a naked girl with a Dave wig and glasses doing a Top Ten list.) “Oh my god,” she said. “He should totally check it out!” I told her I thought there was no chance he would … but maybe, because she had enjoyed it so much … she could “do a little ‘dance’ for Dave for his birthday?”

OK, obviously this was a completely inappropriate suggestion — this was before publicists insisted on listening in as their clients did their phone pre-interviews, as many do today — and Drew would have been in her right mind to be outraged. But instead she said, “Do you think he’d like that?” I said, “Uh — he really doesn’t get out at all — I’m sure he would.” The truth was I wasn’t sure, and if I’d really thought it through, I might have backtracked. Dave always emphasized keeping the show’s humor “above the belt.” But I also knew this had the possibility of being an iconic moment, even if it might jeopardize my job.

Drew, great sport that she was, agreed to go along with it, with the caveat that I not tell Dave. She wanted it to be a true surprise … and was also worried she might chicken out. I told her that if she got on the desk and faced Dave, only he would see if she flashed him, not the audience or anyone else. I only told Paul Shaffer that Drew might do a “little sexy birthday” dance, so maybe he could prepare some “vamp” music. But as it got closer to showtime, I started getting a little nervous. I decided to ask Morty what he thought. He said, “Your call, Danny.” I remember arguing back, “No, it’s your call — you’re the executive producer!” He smiled and walked away. I could tell he was not going down with me if this ship sank. I decided to risk it. And thankfully for me, Dave seemed genuinely (and happily) surprised by Drew’s generous birthday gift.

Joe “Joe Dogs” Iannuzzi, the Mafia Chef

One of my other responsibilities on the show was booking authors. That was a great bonus — I remember one hiatus reading Martin Amis’s Money, and the next week Dave let me book him on the show. But it definitely wasn’t always that glamorous. Mostly I would sift through boxes of random books, looking for potential guests. It was in one such box I found The Mafia Cookbook, written by Joe “Joe Dogs” Iannuzzi, a part-time chef who was also a former mob enforcer for the Gambino crime family — before he flipped and testified about the 1985 assassination of famous boss Paul Castellano.

I called his publicist about booking him for a cooking demo, but she said he couldn’t because he was in the Witness Relocation Program and living in Arizona. However, the next day she called back to let me know Joe was willing to give up his protective status to come on the show. I called him in Arizona, and he sounded like Henry Hill at the end of Goodfellas, bemoaning how this was “no life”; the FBI told him that if he came on the show he would lose his status, but he didn’t care. He only asked that we not advertise his appearance, since many, many people wanted him dead and a lot of them were in New York.

I spoke with Dave and Morty about it, and everyone seemed fine, so we booked him. The day before his appearance, reality set in and more sensible heads noted that having him on was crazy. What if, say, a stagehand got wind of the booking, and something happened to Joe after — or even during — the show? Morty told me to “unbook” him. This wasn’t so easy. His publicist was alarmed that we were canceling — and since this was before cell phones and Joe was driving from Arizona, no one could reach him. The day of his appearance (at the time we’d scheduled for his rehearsal), a page called and said Joe was downstairs waiting for me in our green room. I was, I’ll admit, a little hesitant to deliver bad news to a former mob enforcer. I asked Morty to come with me, but once again, he said it was all me (tough love!). So I went downstairs. I didn’t candy-coat it; I told Joe it had become a safety issue. He went ballistic. “I drove all the way out here from fucking Arizona! I gave up my protection status! Do you know what that means??!” I tried to stay calm and started scrambling, telling him I’d try to get him on Conan or Regis. (Let them take their lives in their hands.) He stormed out, rightfully enraged that he’d been “bumped.”

Later that day, during the taping of the show, he called the office looking for me. Because I was on the set, the intern at the front desk asked if she could take a message. This did not go over well at all with Joe. She came down to the studio, crying, saying he had told her, “You tell that fuck he’s going to get his.” One of the security guys on our show was former FBI, so he made a call — and for the rest of the week I was assigned an FBI escort to bring me home and to work. The next morning, Joe Dogs did an interview with Bob Herbert, then the Mob writer for the Daily News; in the article Joe said, “[Dave] thinks he got a problem with that Margaret Ray showing up in his living room. Wait until he gets home one night and finds me waiting for him.” This was going from bad to worse. I went to apologize to Dave and tell him what Joe had said. Dave was typically unshaken. “Give him my address,” he said. “He’d be doing me a favor.”

Two quick postscripts. First, since Joe had threatened me, he put himself in danger of going back to prison (not a good place for a Mob turncoat). The FBI reached him, and he called me later in the week with a seemingly earnest apology. We forgave each other. Secondly, the last-minute replacement for Joe Dogs that day was the late comedian Bill Hicks; this was the night his un-vetted act (the one where he talked about how pissed Jesus was going to be when he comes back and sees everyone wearing crucifixes) was famously pulled by the censors. So remarkably, by the end of the day, the Joe Dogs debacle had almost been all but forgotten. Such are the vagaries of live television production.

Julia Child

On a less treacherous cooking note, I was assigned Julia Child to produce in 1993. Dave loved having great chefs on, not just because his cooking demos were always colorful, fun TV, but mostly because these culinary masters would make him their famous dishes. I was told Julia wanted to make her bananas Foster. Dave rarely dines out, and the idea of him having Julia Child on making a dessert rather than one of her signature dishes was fine — but frankly not ideal. Dave didn’t want to make a big thing of it, but asked me if I could see if she could possibly make an entrée instead. So as we wrapped up our 6 a.m. pre-interview, I broached this with Julia as delicately as I could, saying, “You know Dave doesn’t really get out for dinner much. He was wondering, if it’s not too much trouble — would you ever consider making him an entrée instead of a dessert?” There was a long pause, and then in that famous high-pitched, pinched tone, she said, “You tell David Letterman not to be so fussy. He’s not the Queen of England, you know. I can be pretty fussy myself.” It was all I could do not to laugh, because all I could think about was Dan Aykroyd’s famous impression on Saturday Night Live. She added, “I will make him bananas Foster — and if he doesn’t like it, tough cookies.” She was wonderful, and she was right: Dave enjoyed his bananas Foster.

Sean Connery

In 1993, Sean Connery’s publicist called to book her client to dispel rumors that he was suffering from throat cancer. (I’m not telling tales out of school: He went on to discuss it on the show.) She wanted to show he was virile as ever, and suggested he make an entrance — on a bicycle. “A bicycle?” I said. Surely she was kidding. “He’s James Bond,” I said. “He can’t come in on a bicycle! He should fly in on a jet pack!” Easier said than done. We hired the famous Flying by Foy company out of Philadelphia (which handles rigging for everything from circuses to movies; most recently it made Allison Williams fly for NBC’s live Peter Pan), but this was not to be a glamorous entrance. Connery, then in his sixties, had to be strung up high into the rafters among the lighting rigs with a harness tightly snugged around his crotch (and under his pants) an hour before the audience was loaded in so they wouldn’t see him. He dangled, suspended in this truss above the stage, silent and unseen, in great discomfort, through Dave’s monologue and the first two comedy segments. Then he was finally lowered on wires by a couple of stagehands, with two hand-squeezed fire extinguishers shooting out white clouds behind him to suggest it was a real jet pack. It wasn’t exactly George Lucas/Industrial Light & Magic, but it worked, and TV Guide called it the “Entrance of the Year.” Even so, it was painfully obvious Connery was less than pleased with me as I walked him off the stage; he was grumbling and clearly thinking only of his misery rather than the triumph of his appearance.

Julia Roberts

When she came on in 1994, it was only her second appearance since making her debut on Letterman in 1989, and now she was arguably the biggest female movie star in the world. And as such, her agent, Elaine Goldsmith-Thomas, told me Julia didn’t want to do a pre-interview. This meant there would be no safety net; Dave would just ask questions and hope they would lead to interesting conversation. And because this was her first appearance since becoming such a huge star, no one really had any idea what to expect. At best, it was a dice roll — unpredictable and awkward silences are no fun on talk shows. Dave asked me if I thought she’d do the pre-interview with him. This had never really been offered up before, and Julia agreed. I sat with Dave as he called her.

Dave: “Hi, Julia, just called to thank you for agreeing to be on the show …” Julia: “Well, thanks for having me.” Dave: [Pause.] “So … what do you think you want to talk about?” Julia: “I don’t know. What do you want to talk about?” Dave: [Even longer pause.] “I don’t know. I guess we’ll figure it out when you get here …” [Hangs up, turns to me.] “Jesus Christ, how do you do those?”

As if doing a pre-interview were in some way more difficult than doing the actual interview. But Dave was always very quick to give us all the credit — and to take the full blame if something went wrong. Of course, they got along ridiculously well — and to the end, she continued to be a favorite guest. But here’s a funny sidebar, and one that at the time was maybe the highlight of my young showbiz life: Julia was promoting a movie she had done with Nick Nolte called I Love Trouble, in which she played a pickpocket. (Hey, it was the ’90s …) A big talk-show goal is to have a guest “get out of the chair” and do something physical, so I thought it might be something if she tried to pick Dave’s pocket. Before the show I went to her dressing room and asked if she had studied how to actually pick pockets. She said yes. I asked, “So, you think you could pick my pocket, and I wouldn’t be able to tell?” Confidently, she said, “Definitely. You have a wallet? What pocket?” Me: “Left, back.” She said, “Stand up.” I stood. She grabbed me by the neck and kissed me on the lips — at the same time taking the wallet from my back pocket. Her: “You feel that?” Me: “Nope.” I did not tell my then-girlfriend about my day at work. And alas, while there was a palpable TV flirtation between Dave and Julia that night, Dave never got his pocket picked.

Madonna

In 1994, if Julia Roberts was the biggest female movie star in the world, Madonna was arguably the biggest female star. At the same time, due to her pioneering promiscuity and her seemingly insatiable interest in surly actors, athletes, and rappers, she was also endless fodder for the tabloids — and late-night hosts. Dave loved her; she was the gift that kept giving. (As he was fond to repeat back then, “I have a theory about Madonna. I think she likes to shock us.”)

So we were very surprised when she agreed to come on the show. I spoke with her longtime rep, Liz Rosenberg, and she said Madonna was interested in coming on and basically giving it back to Dave — a little reciprocal ball-breaking, as it were.

This was, hypothetically, a problematic plan. Not that he couldn’t handle her, but Dave was a professional comedian. Madonna was a professional singer. This could go south quickly if un-reined. (Maybe you saw Madonna’s painful recent attempt at stand-up on Jimmy Fallon?)

After discussing it with Dave, I proposed a plan I thought was pretty bulletproof, that would make her look good, be “funny,” and satisfy her larger goal of making Dave squirm. I got on the phone with Madonna, who was surprisingly and truly lovely, and pitched my idea: How about you go on and complain that he’s been taking shots? He will say it’s exaggerated, he loves you, etc. — and then you say, “Oh yeah? I actually brought some tape from the show.” And then you show, in succession, three of the most horrible jokes he has told — and ask him to explain each one. That ensured his awkwardness — and the laugh. She signed off on the plan without hesitation. I then went and told Letterman I’d had a great talk with her and that she was super-engaged and receptive to the idea — and unless something went terribly wrong, I thought we were in good shape.

The day of the show, she arrived to much fanfare and press anticipation, but with no entourage. Her only accompaniment was her makeup person, Kevyn Aucoin. I walked up to her dressing room, knocked on the door, put out my hand, and said, “Hi, I’m Daniel.” She didn’t get up or offer her hand. Instead she said, “Suckmadick.” I took a beat. “Sorry?” She looked at Kevyn, smiled, and said it again, slower, like a petulant 8-year-old child challenging a parent: “Suck–ma–dick.” She and Kevyn began laughing hysterically. Immediately, I thought: We’re screwed. I smiled wanly and powered on: “Ha … OK, so this will pretty much go as we discussed. We’ve loaded up three pieces of video, each one worse than the other, and after each one …” She stopped me. “That’s too much to remember.”

Hmmm. I paused, now more annoyed than anything. “Uh, not really. It’s actually pretty simple — you show a tape. Get his reaction. Show another. Get his reaction. There are three …” “Yeah, I’m not going to remember all that.” Me, trying not to let my voice break and betray my now very urgent concerns: “Why not?” She started giggling again. “We smoked a little endo before we came here …” Fuccccckkkkkkk!!!!

I went down to Dave’s dressing room, which I tried not to do before the show. “We’re in trouble.” Very graciously, he didn’t tell me “I told you so,” instead, knotting his tie with a slight grimace, seemingly bracing himself for the storm.

The intro I wrote probably didn’t help matters: “Our first guest tonight is one of the biggest stars in the world, and in the past 10 years she has sold over 80 million albums, starred in countless films, and slept with some of the biggest names in the entertainment industry.” But there was no way we could have anticipated what followed. It was the most censored late-night broadcast in television history, with Madonna saying “fuck” 14 times. She took off her underpants and complained when Letterman wouldn’t smell them. And if you think Letterman was happy about all the subsequent attention and newspaper coverage the interview brought, you’d have guessed wrong. He always understood the privilege that came with the ability to broadcast, and the responsibility that accompanied it. Ratings and press were less a consideration.

Compounding matters was the fact that Madonna would not leave the stage. We bumped the next guest (a grocery bagger — an annual human interest competition winner that Dave, a former bagger himself, genuinely always enjoyed). Dave tried to say goodbye again. She wouldn’t leave. Counting Crows was just about to make its network television debut — and we were going to have to bump the band if Madonna didn’t budge. Sheila Rogers, the talent executive who has possibly given more bands their first breaks than anyone in the history of TV, went to Morty to ask what was happening. Morty then turned to me and said, “Get rid of her.” I said, “How am I supposed to get rid of her?” But the implication was clear: This was a problem I’d created, and now it was up to me to salvage the rest of the show. As Paul and the band blasted their mid-break song, I walked onstage and said loudly, “Say hi to the audience.” Madonna waved. As she waved, I took her hand, as if I was helping her up — and I did, in fact, lightly pull her up. And over the band I said loudly again, “Say goodbye …” Confused, she waved. Still holding her hand I led her offstage.

Peter O’Toole

We booked Peter O’Toole when Late Show went to London for a week in May of 1995, and I was thrilled to produce him — he was definitely one of my acting idols, and known to be one of the great talk-show raconteurs. This was also an important Sweeps period for us — and doing shows from London seemed less than a sure thing. So I started the pre-interview call with O’Toole with an enthusiastic pitch: “I was thinking you could do one of two entrances: Like in My Favorite Year, you can come in on a rope …” [Long pause, no response.] “… or, like in Lawrence of Arabia, you can come in on a camel.” [Even longer pause.] Then he said, “Young man, I will not be coming in on a rope … and I certainly will not be riding in on a camel.” I expected this resistance, but pretended I did not. “Please, Mr. O’Toole, these shows are so important. And the audience would go crazy.” I futilely tried to appeal to his ego. “It would definitely be in every newspaper and magazine …” “No,” he said firmly. “I am sorry.” (Even though clearly he was not.) Me: “Is there anything I can do to change your mind, any circumstance in which you’d reconsider?” [The longest pause yet.] I could tell he was beginning to feel sorry for me after dampening my youthful enthusiasm. He offered this: “If you were able to find me an Arabian racing camel, I might — might — consider it. But it is highly doubtful you will find one in England …” That was all I needed to hear.

With our team of researchers and production assistants, we began calling all over England — circuses, zoos, everywhere we could think of. And then we found one. The day of the show, O’Toole arrived at the studio and I was there to meet his car; I had a huge smile, and as we turned the corner into the loading dock, I presented him with his Arabian racing camel. “Ta-da!” I smiled. His smile quickly turned to a scowl: “My dear boy, that is not an Arabian racing camel — that is a common zoo camel. I most certainly will not be making an entrance on that.” The way he said “zoo” made it sound like it was the filthiest vermin he had ever laid his eyes on. I was in trouble; I was desperate. “Please, this cost $3,000 to have shipped. I’ll lose my job!” (OK, it was a small white lie for the greater good.) The truth was, even though riding in on a camel might seem trite (or worse) to him, I knew it would be a great moment. Very, very reluctantly, he agreed.

Daniel Kellison

Still, I was obviously unhappy with the trainer who had blatantly lied about his “Arabian racing” camel. Because we were also doing a British version of “Stupid Pet Tricks” on that show, I asked if the camel could “do” anything — sit on command, make a noise, anything. He said, “No, it’s just a camel.” But then his friend said, “She enjoys a sip of lager every now and then …” What? “Give her a can of lager, she’ll fight you to drink it all …” So that night, after Peter entered the theater on his camel — to huge applause — and dismounted, he took a moment before moving to Dave’s desk and pulled a big can of Heineken from his pocket, opened it, and gave it to his trusty steed. The camel chugged all 24 ounces and spit the can on the ground. Peter turned to Dave and said, “I think that’s called a Stupid Pet Trick …”

Paul McCartney

There was a standing offer of $500 from Dave to anyone who booked a Beatle on the show. In 1989, Morty booked Ringo Starr and went to Dave to collect his money. Dave told him, “Ringo doesn’t count.” I really wanted to book Paul McCartney — and actually had a connection. My first four years on the show, my girlfriend and I were sharing a two-story duplex apartment on Morton Street with another friend and his girlfriend, Louise Eastman, who was Paul’s niece. I’d also become somewhat close to Paul’s daughters, Stella and Mary — and subsequently became friendly with Paul. But one night at dinner I had also witnessed a woman we were eating with ask Paul for a picture, and he had very gracefully declined, telling her, “Either you are a friend or a fan. You decide, dear, but you can’t be both.” I loved Paul, and being a kid from a small town in Vermont, I couldn’t help but be in awe any time I was in his presence. And Paul was every bit as personable and warm as he appears in interviews. Quick with a story or a song (which always made everyone just stop cold — because this was, instantly, the coolest moment of everyone’s life), he was very eager to talk music or anything else.

So, ambivalently, I decided I was going to try to book Paul — but I didn’t want to ask him directly. I wanted to remain “a friend.” So instead I struck up a “professional” relationship with his affable publicist, Geoff Baker. And I’ll cut to the chase here — it never happened. But I did get a cool story out of it. While in London, we were staying at a Sheraton in Knightsbridge. I had arranged to meet up with Stella and Mary, and they told me to meet them at the Hyde Park Hotel, which was across the street. So I was waiting in the lobby, and Morty — who, by coincidence, was staying in the same swanky hotel — came in and saw me, and gave me a look like “What the fuck are you doing in here?” I said I was meeting a couple of friends and left it at that. We talked for a couple of minutes — and then all a sudden Morty’s face turned sheet-white: “Holy fuck, look at that …” And out of the elevator came Yoko Ono, Sean Lennon, Ringo Starr, George Harrison, and Paul McCartney with Stella and Mary. Stella and Mary waved to me. I waved back, and then from Paul came the hearty hello: “Dan the Man!” Morty looked at me like I was from Mars. And then I got to introduce Morty to Paul — and we both got to meet Yoko and all the remaining Beatles. And I realize there’s basically no way to write this story without it sounding like a complete brag, but it was definitely one of the coolest moments in my career. And in the end, I may have never booked Paul, but, for that moment, I was perfectly content to be more friend than fan.

After eight years at Letterman, Daniel Kellison (@Danielkellison) left to executive produce Rosie O’Donnell’s daytime talk show — from which he was unceremoniously fired eight months later. Soon after, he cofounded Jackhole with partners Jimmy Kimmel and Adam Carolla, and later helped launch and executive produce Jimmy Kimmel Live. Besides being an occasional contributor to Grantland, he has since formed the multiplatform comedy network JASH with partners Sarah Silverman, Tim and Eric, Michael Cera, and Reggie Watts.