Welcome back for Part 2 of "The Litterbox of Late Night" brought to you by our late night talk show expert John Maddi!  This episode takes us from David Letterman through present day of our night hosts with the mosts.  Also provided are useful cat portraits of these late greats!

By 1992, The Tonight Show Starring Johnny Carson had aired for 30 years. While the late night format existed since the early 40s, it was not until the end of Carson’s tenure that the show established and perfected the 6-part format that was discussed in part 1. But if you were to have stayed up past Carson in the 80s and didn’t change the channel, you would’ve discovered that another late night talk show co-existed with it, and it was nothing short of unusual. It was almost as if it was an evolution chain, where one show evolved to perfection and the other evolved way off-course to an imperfection. That perfect imperfection became the late night host that took the format and distorted it in his own style of comedy, later on paving the way for a new generation of late night hosts that idolized as much as they were influenced by him.

And now, the FATCAT that can shed enough fur to make another cat......DAAAVIIIDDD LETTERMAN!!

David Letterman


Letterman grew up in Indianapolis in the 50s and was anything but the television star you know him as today. He was self-conscious and awkward; girls didn’t like him, he was unathletic and got mediocre grades; all the things you can get from comedy gold. His interests naturally drifted towards television, still a revolutionary medium at the time. He grew up watching Steve Allen and Johnny Carson, imitating them as he developed his desire to become a TV personality.

David learned to twist his self-consciousness and awkwardness into a sarcastic, dry sense of humor. In high school he excelled in his public speaking class which helped shape his performance ability, on-stage personality and comedic timing.

Jay Leno said in an interview

“When I first met Dave he was very awkward, but an excellent wordsmith. He would put words and sentences together that were really clever. When he met me I was kinda loud and verbose, like I owned the joint. I think from Dave I learned to how to put words together better. When I would go on his show, we would play off each other so well. Letterman always liked the joke on the way to the joke more than the joke itself. I would talk to him about something, and there would be like 5 or 6 jokes about the story before I would even get to the punchline to the actual joke. He was very good at weaving things together like that.”


Early Comedy Attempts

At an early stage, Letterman was developing a comedic style which subtly mocked the format he was using.   During his college and post-college years Letterman took on-air broadcasting jobs that would traditionally have a serious, monotone natured personality. He present the material, but would poke fun at it, sometimes imperceptibly, sometimes more directly. He seemed to be entertaining himself as much as if not more so than his audience.

Around the time of Letterman's retirement in 2015, Conan O’Brien wrote an essay about Letterman describing him and Carson as yin and yang. “Johnny did the talk show; Dave did the anti-talk show.” 

Below are clips of Dave giving a weather forecast and hosting Clover Power.


The Morning Show

Letterman soon became a regular guest on The Tonight Show and became a favorite for Carson. NBC appreciated his talents to the point where he was offered his own show. But it was not the late night show that solidified David's success today. The David Letterman Show, a live morning talk show which aired from June to October of 1980 gave Letterman his first shot at the talk show format. The problem was the intended audience: housewives. In hindsight, one could consider the NBC executives comedic geniuses for thinking David Letterman could cater to middle-aged women and the audiences of The Price is Right and Laverne & Shirley.

Steve O’Donnell, Letterman’s head writer from 1988 to 1992, commented on his morning show saying “When I first watched him in the morning, I was attracted to the fact that he was unlike other broadcasters. It was as if he didn’t belong there. He would speak in a normal person’s voice rather than a broadcaster’s voice.”

The show contained some strange (yet very Letterman-esque) segments. One example was the on-the-street bits where Dave and guest Steve Allen look at a camera that is rolling along 6th Ave in Manhattan and comment on the people walking by, treating it like a fashion show. Another strange bit happened between commercial breaks, when the screen would show a staff member’s resume with all their personal information on it.

Letterman’s girlfriend at the time, Merrill Markoe, became his head writer for the show. Markoe had a sense of humor that was very similar to Dave’s and would often give him her jokes and bits. Despite the couple having similar tastes in humor and aiding Letterman to solidify his comedic style, the morning show was not well-received for the demographic it was targeting and was ultimately deemed unfit for its time slot. 

But regardless of any of the backlash, Dave’s morning show gains a cult following as seen in the audience on his last episode.

Late Night

The morning show’s final episode aired live on October 24, 1980. Despite being cancelled, NBC still wanted to keep Dave and signed a holding deal with him for the next 2 years. In 1981, he guest hosted The Tonight Show while NBC figured out what to do with him. In November 1981, NBC along with Carson Productions and Space Age Meats (Letterman’s production company at the time) conceived a late night show that would air right after Carson at 12:30am. His brand new show, Late Night with David Letterman, was the result and had two goals in mind: to resurrect the spirit of his morning show and be the first to cater to the young male demographic. NBC showed little to no interest in micromanaging the show so that lead the writing team to push boundaries outside of the mainstream talk show format. Contrarily, Carson Productions, which owned the 12:30 timeslot along with The Tonight Show, became the control freak. They wanted to make sure that Letterman’s show had as little resemblance to Carson’s show as possible. Letterman could not have a sidekick like Ed McMahon or have a long monologue like Carson. Paul Shaffer, Dave’s bandleader, could not have a horn section. So instead Shaffer put together a band that was more rock and synthesizer-based, a first for a late night

band. He also could not book any of Carson’s signature guests like Buddy Hacket or imitate bits like Carnac the Magnificent.

Late Night with David Letterman debuted on February 1, 1982 and picked up right where he left off with the morning show with the peacock girls.

His Own World

Late Night quickly gained popularity with its targeted demographic, being praised for its wackiness and unpredictability. In the first episode, Dave takes the viewers through a tour of Studio 6A where the show is taped. One instance is when he enters the “green room” which is usually a room for guests waiting to go on. But once Dave opens the door, the room is instead filled with plants and vegetables. “These are some of the vegetables at NBC not in programming.” says Dave as he passes through the room, with audience laughing in a way where they knew it was wrong to crack a joke like that. He then goes into the control room, building it up for the audience to think it will be a mundane room with buttons, only for him to open the door to dozens of people having an Irish party with lots of drinking and loud music. When the show goes back on air after break, one of his producers is seen crawling on the floor to his spot to avoid being on camera. Naturally, Dave uses that as an opportunity for comedy.

The wackiness and unpredictability was not just limited to the sketches on the show, guests would play along as well. In an early episode, baseball player Hank Aaron was a guest on the show and right after the interview, the cameraman followed him backstage where someone else would give him a post-interview like they do in sports tv. This is in the clip below at around the 8:30 mark.

Unwelcoming Guests

With the show’s unpredictability, a handful of celebrities went on record saying they were afraid of appearing on the show. Sometimes an interview wouldn’t go well and would turn into a verbal sparring match with the guest. One famous example is when Cher was a guest on the show and called Dave an “asshole” on network television.

The show also has had guests where the situation got physically dangerous. Andy Kaufman and Jerry Lawler fighting each other on set and Crispin Glover almost kicking Dave in the face are perfect examples of this.

Sketches (Viewer Mail, Top 10, On Location)

The only real difference between the morning show and the late night show was that one audience group appreciated him and the other despised him. Letterman had a lot of signature sketches that defined what his show was and used almost throughout his entire tenure as a late night talk show host. But what a lot of people forget to realize is that a lot of these sketches originated from the morning show. While the sketches back then were more than enough for Letterman’s style, the late night show was an opportunity to evolve them. One sketch called Viewer Mail was when Dave would read fan mail on the show. Often times the letters would be strange or ironic comments towards Dave and the show. In this episode, not only does Dave answer the Viewer Mail, but he goes all the way to Hicksville, NY to answer the fan’s question himself.

Stupid Pet Tricks was another staple in the late night list of sketches that also carried on from the morning show. Simply put, a person would bring their pet onto the show and it will perform an unusual trick. Letterman took it even further by introducing “Stupid Human Tricks”.

The Top 10 List is perhaps Letterman’s most popular sketch in his late night arsenal. The Top 10 was derived from celebrity tabloids and good housekeeping magazines that would put together lists like “Top 10 bachelors in NYC” or “Top 10 scented candles to use in your bathroom”. Steve O’Donnel, one of Letterman’s head writers, said that “Why, we can put together such nonsense ourselves. And we did!” Letterman did the Top 10 sketch from 1985 all the way up to his retirement in 2015, putting together over 4600 Top 10 lists. Below is a clip of the very list.

Steve Allen was the pioneer for doing on-location sketches such as asking people on the street stupid questions or making comments to see how people would react. Allen was one of Letterman’s biggest influences so he naturally integrated it into his show. Not only did Dave do on-location bits at other people’s expense, but there were also times when it was at his own expense. In 1985, General Electric bought NBC, with the takeover taking full effect the next year. In 1986, with the merge near completion, Dave and his camera crew take a trip to the Manhattan location of GE to offer them a fruit basket. GE was not too happy with his visit, and Dave got a taste of his own medicine.

Transitioning Time Slots

David Letterman’s tenure at the 12:30 timeslot provided 11 years of original content that shook up the late night scene. In 1993, Dave was the first late night host to transition from 12:30 to the 11:30 timeslot. He stated that as the years went on doing his show, his audience grew older and wanted to keep his audience. This was also the first instance where late night television had an outside controversy, where Dave secretly wanted to take over The Tonight Show but it was ultimately given to Jay Leno instead. Despite this loss, Dave started his new 11:30 show on CBS in August 1993 and retired in May 2015. A lot of his sketches and humor carried over, though as he got older a lot of them died out

and eventually became a mainstream host like Carson. Robert Morton, one of Letterman’s producers until 1996, stated that the transition was inevitable. “When you’re in your 60’s and still doing outrageous things, you just come off as ridiculous. So there needs to come a time where you have to stop innovating and just be content with the normalcy.” Morton best described the difference between a 12:30 and an 11:30 show by referencing a magic trick. “On the 12:30 show a magician would perform a magic trick and screw it up as part of the bit. But on an 11:30 show, you would want the trick to succeed. That’s the difference between the two timeslots. One celebrates failure; the other celebrates success.”

The retirement of David Letterman did not go unnoticed. Just about every late night host after him since the early 90’s was greatly influenced by his comedy and proudly continued his legacy in their own way.


Conan O’Brien

Conan's entry into late night television is perhaps the strangest thing to ever happen in the television business in general. Aside from being an established writer for Saturday Night Live and The Simpsons, he was widely considered an unknown. At the time he had about 40 seconds of on-air acting experience because he was an extra in an SNL sketch that Tom Hanks was in (The Five Timers Club). But as far as being considered a replacement for David Letterman for the 12:30 timeslot when we he left for CBS, he was far from being on the shortlist. The only person who saw something in him was SNL executive producer Lorne Michaels. Lorne's talent was finding the talent in other people, which is why so many SNL alumni moved onto elaborate movie and tv show careers. But Conan was a special case to Lorne because Conan was a talent that was yet to be recognized. When Conan auditioned for the 12:30 timeslot, one of the NBC executive Warren Littlefield asked him what kind of show he would put on. Conan told him:

"Letterman's done irony. He's done the anti-talk show. This show has to have a different quality. I think now is the time for silliness. Dave has that dignity and personal space, but I don't do that. We're going to have things like plants in the audience, not unprofessional performers like Dave uses. I want actors on the show that will commit. If someone in the audience stands up and pretends to be a gold miner, it will be a professional actor playing a gold miner. The show will have a bit of Pee- Wee's Playhouse to it. We'll have puppets, we'll try to use animation. We'll have fake guests. We'll have a reoccurring gag where a fake guest gets bumped every night and gets very passive aggressive about it."

Conan was announced as David Letterman's successor in April 26, 1993 and started his show September 13th of the same year. Nowadays when someone is announced as a late night host successor, not only are they already established in the business, but they also have a year at most to get things ready. In television business-time, April to September is considered a nano-second. Conan's first show had a cold opening skit that was reminiscent of something you'd see on SNL. Being an established writer, opening his show like this I'm sure made him feel in his element. The cold-opening was a response to the media putting pressure on him due to his inexperience and lack of fame.

Tom Shales, writer and critic of television, panned Conan’s first couple years of his show. He wrote:

"As for O'Brien, the young man is a living collage of annoying nervous habits. He giggles and titters, jiggles about and fiddles with his cuffs. He has dark, beady little eyes like a rabbit. He's one of the whitest white men ever.”

Conan’s show even got to the point where his relationship got toxic with NBC, with them secretly trying to replace Conan with another host. Instead of Conan backing down to the negativity of the affiliates and critics, he took that energy and made it part of his act. Letterman always celebrated failure and self-deprecating humor. But Conan took that part of Letterman and took it to a new level by incorporating it into almost everything he does and turned the show into a hit. Below is a compilation of technical errors and bloopers on his show, and shows how he played it off as his strengths.

Jon Stewart

Jon Stewart was another indirect disciple of David Letterman. Stewart had a late night talk show on MTV in the early 90’s, but ultimately took over The Daily Show in 1999 up until 2015. The Daily Show is a half hour program with a niche in mocking news stories and politics. Craig Kilborn hosted the show before Stewart and its content was mostly on par with Saturday Night Live’s Weekend Update, poking fun at celebrity gossip and mundane politics. Stewart continued that trend for the first few years in his tenure until 9/11 happened. The show returned to the air the following week after the attacks with a “no more bullshit” undertone. Stewart was pissed, and he wasn’t letting anyone get away with anything. Letterman was always one to make fun of people at their expense, but it was always regular civilians that he poked fun at. Stewart took that style of humor and took no prisoners. Below is one of new segments that was conceived to confront all the political madness that was going on at the time.


Stewart did not just make fun of politicians on his show, but he was also brutal to them on their own shows as well. Below is a clip of the infamous episode of Crossfire with Jon Stewart as guest back in 2004. Stewart called out Tucker Carlson for catering to the politician’s ego and that they were “hurting America”.

Stewart summed up the experience on his own show the following day: “You see, the problem with telling people that their show blows on their own show, is that they’re there to hear it. And they retorted back saying I wasn’t being funny. And I told them I wasn’t here to be funny. I will come back to my own show the next day being funny. And when I leave your show to go back to mine, your show will still blow.” Crossfire was cancelled a few months after his appearance and Stewart became a voice for millennials who needed guidance in a world of corrupt politics.

Stephen Colbert

Stephen Colbert is best known as his on-air persona: Stephen Colbert. Colbert made his late night debut as a senior correspondent on The Daily Show in 1997. At first his character was just a regular news reporter getting himself into strange and silly on-location pieces. But in 1999 when Jon Stewart took Craig Kilborn’s place as host, the Colbert character started to gain a point of view in politics that developed to the point where he started hosting his own show, known as The Colbert Report.

Colbert’s character was best described as:

"The Colbert Report was meant to be a parody of right-wing character driven news shows such as Bill O’Reilly and Glenn Beck. Below is a clip of a promo of the show 2 years before it became an actual show, when it was only a joking thought.

Craig Ferguson

Craig Ferguson followed David Letterman on CBS for 10 years. Ferguson is perhaps the blackest sheep of all the late night hosts because not only does he not cite Letterman as an inspiration, but he actually pulls off the wackiness part of Letterman better than any of the others. Ferguson is one of a kind as he made almost every part of the 6-part format of late night fine-tuned to his liking:

    He improvises all of his monologues. He just simply picks a few topics and he just rambles on with whatever comes to mind.

    He has no house band. However, he used be in a band when he was in Scotland and is trained in playing guitar, bass, drums, and other instruments. He is shown in the intro of his show singing and playing the drums to his own theme song.

    He has a robot skeleton as a sidekick named Geoffrey.     He has a bunch of hand puppets that he uses in sketches and sometimes the monologue that he performs all himself.

    He has a bunch of crazy kooky characters such as someone in a horse costume, exotic dancers, secretaries, and people dressed like they are from the 60’s to break into a dance number out of nowhere for no real reason.

    He talks about Doctor Who at any opportunity he gets and even has memorabilia of the show.  He had an episode dedicated to the show and interviewed the current cast at the time.

    He was the first to use the monologue to openly disclose personal things in his life. He used it to eulogize his mother, reflect on becoming a US citizen, declared he would not make fun of Brittany Spears during her public meltdown because it reminded him of his time as an alcoholic, noting that he has been sober for over 15 years.

This clip pretty much sums up everything about Craig Ferguson’s late night show.


Jimmy Kimmel

Jimmy Kimmel was another comedian who both idolized Letterman and eventually got his own late night talk show. Kimmel followed a route to stardom similar to Letterman: he got his start on radio and got fired for outrageous content, he hosted a couple shows such as The Man Show and Win Ben Stein’s Money, and then ultimately got his shot at late night on ABC. What makes Jimmy Kimmel special to the world of late night (as well as an honor to David Letterman) is that he is a pure Brooklyn-born no nonsense wiseass. When Jimmy Kimmel does his monologue, he does not tell a series of jokes with punchlines. He tells a story about a particular topic. And when it’s a story about something in the news about today’s celebrity gossip or trends, he talks about the content in a way as if he knows it’s ridiculous. It’s almost as if he is too smart for the late night talk show format and secretly wants to scrap it away and perform an explicit comedy routine. Below is a clip of one of his monologues about “National Unfriend Day” for Facebook. Pay attention to the look on his face as he explains this to the audience, as if he is saying “Are you fucking kidding me? This is really a thing?”

Kimmel has never pulled any punches when it came to his wit. What makes him really dangerous is that his show for a while was taped live, hence the name of his show Jimmy Kimmel Live!. Despite the name, Kimmel’s show actually doesn’t air live anymore. The final nail in the coffin for removing the live taping part of the show was the network’s inability to keep up with censoring Thomas Jane’s excessive swearing. But that never stopped Kimmel’s impromptu comments from being censored on television. Jimmy Kimmel always believed in “television moments”, something that happened on a show that became immortalized for the genre of tv. Kimmel had one of those moments in 2010, when he was a guest on Jay Leno’s 10pm show during a huge controversy at NBC with Leno and Conan O’Brien over The Tonight Show. Kimmel made it clear that Leno was wrong for going back to The Tonight Show and he wanted to make it known for all American television viewers how he felt.


Jimmy Fallon

Jimmy Fallon is a return to form with late night television in multiple regards. He brought the 12:30 Late Night show back to being experimental and loose, he is the first to successfully transition from Late Night to The Tonight Show (which was seen as very stigmatic for NBC for a number of years), and is the leading late night show to cater to the current demographic; the millennial generation. For roughly 50 years, The Tonight Show primarily catered to an older demographic, from people who fought in WW2 through the baby boomers and Generation X. But once the internet and social media became mainstream in the early 2010’s, late night had a more interactive approach. Late night shows started creating Facebook pages, Twitter and Instagram accounts, Youtube channels for you to watch highlights of the show. There was no longer a need to wait until late at night to watch late night. While this may dilute the value of late night television, it also had its advantages as it gave the fans a way to connect with their late night hosts in a way never done before. Fallon would give a topic to post on Twitter such as “What was your worst birthday present?” and Fallon would read the best responses on the air. There would be behind the scenes such as rehearsal monologues, or extended interviews that were only exclusive to online. It was Fallon’s incarnation of The Tonight Show that perfected the “viral video”. All of the Youtube videos on Jimmy Fallon’s page averages in the millions.

Fallon has a background in sketch comedy, getting his start in show business as a member on Saturday Night Live. His time on that show displayed all his celebrity impressions and musical talents; 2 things that easily translated into late night. The show displays both talents with bits called Wheel of Celebrity Impressions and Wheel of Musical Impressions.

Even though Fallon’s Tonight Show represents a new generation of viewers, pop culture from the past has not been forgotten. Lots of millennials have become fond of movies from the 80’s and 90’s that they grew up with through having the movie on DVD or on a streaming service. There have been a few occasions where a classic movie or character made an appearance and reenacted a memorable scene. Below is a clip of Kevin Bacon, who was a guest on the show that night, reenacting a dance number to Footloose.


Fallon’s Tonight Show has also played a few homages to Carson as well as Letterman. One of Jimmy’s signature bits is playing games against either an audience member or that night’s guest. The premise of the sketch is that they take a normal game and put some wacky twist around it. In this case, it’s a game of beer pong only the balls and the cup are giant size. This is actually a bit of an homage to a Letterman sketch back in the 80’s, where he would take 3 audience members and he would pit them against each other in a race to the elevator to see who would make it down to the bottom floor of Rockefeller Center first. Another sketch that Fallon does is called “Brain Storm” which is very similar to Carnac the Magnificent.


The Failure and Success Through Imitation

In May of 2011, Conan O’Brien was giving a commencement speech to the graduating class of Dartmouth College. It was 16 months at the time since he left The Tonight Show because he refused to move the show to midnight in favor of Jay Leno’s half hour talk show (long story). Conan left the whole debacle with class and dignity. He gained the support of millions of fans over the internet and was made one of Time Magazine’s 100 most influential people of 2010. After a barrage of jokes about the college in his commencement speech, Conan shifted gears to a more serious tone.

“In 2000, I told Harvard graduates ‘don’t be afraid to fail’. But in 2010 I experienced a very public and profound disappointment. I did not get what I wanted.  But then something spectacular happened. Fogbound, with no compass, and adrift, I started trying things. I grew a strange, cinnamon beard. I dove into the world of social media. I started tweeting my comedy. I threw together a national tour. I played the guitar. I did stand-up, wore a skin-tight blue leather suit, recorded an album, made a documentary, and frightened my friends and family. Ultimately, I abandoned all preconceived perceptions of my career path and stature and took a job on basic cable with a network most famous for showing reruns, along with sitcoms created by a tall, black man who dresses like an old, black woman. I did a lot of silly, unconventional, spontaneous and seemingly irrational things and guess what: with the exception of the blue leather suit, it was the most satisfying and fascinating year of my professional life.  To this day I still don't understand exactly what happened, but I have never had more fun, been more challenged—and this is important—had more conviction about what I was doing. Way back in the 1940s there was a very, very funny man named Jack Benny. He was a giant star, easily one of the greatest comedians of his generation. And a much younger man named Johnny Carson wanted very much to be Jack Benny. In some ways he was, but in many ways he wasn't. He emulated Jack Benny, but his own quirks and mannerisms, along with a changing medium, pulled him in a different direction. And yet his failure to completely become his hero made him the funniest person of his generation. David Letterman wanted to be Johnny Carson, and was not, and as a result my generation of comedians wanted to be David Letterman. And none of us are. My peers and I have all missed that mark in a thousand different ways. But the point is this: It is our failure to become our perceived ideal that ultimately defines us and makes us unique. It's not easy, but if you accept your misfortune and handle it right, your perceived failure can become a catalyst for profound re-invention.”

All original artwork in Episode 8 ©John Maddi 2016



Works Cited

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15. https://en.wikipedia.org/wiki/Jimmy_Kimmel

16. https://en.wikipedia.org/wiki/Jimmy_Fallon

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