Letterman Head Writer’s Tips For Late Night Jokes

By Gabe Abelson

Writing for late night talk shows is a terrific, logical “next step” for any stand-up comic who wants to break into television. Rather than writing a sitcom or film, which can take months or years, putting a late-night packet together can be done in days.   

Late night is its own, unique animal, and not only have I worked consistently in that medium for twenty-five years, but as Head Monologue Writer for Late Show with David Letterman, a large part of my job was reading packet submissions, so I know what late night talk/variety shows are looking for, and equally as important, what may be in your packet that could look like a red flag to a show’s reader and get your packet tossed. This is essential information to have, as it’s equally important to know what NOT to do, as it is what TO do.

In this class, you will not only learn how to write comedy for late night television, but you will also learn about the political and social aspects of holding a staff writing job, and this is invaluable information— not just landing the job, but KEEPING it. Late night writers only work in 13-week contracts, and the show must let you know by your ninth week if your contract will be picked up.  All through my years at Leno and Letterman, I witnessed many writers hired and fired. And it wasn’t always about the quality of their work. This is where the political and social aspects of the workplace environment come in. It is information you won’t find in any book, but essential information to have, which I pass on to my students.   

So, aspiring late-night TV writers, here are some late night “do’s” and “don’ts” to keep in mind (These are unwritten rules. I’m drawing from my experience of 25 years in television. What I can tell you is, there are definitely exceptions to each one of these rules. In class, I will cover this in great detail):

  1. Late night monologue is observational, as opposed to stand-up, which is personal.  Stand-up is about who YOU are—  your likes, dislikes, fears, etc.  It’s INTERNAL. To be a great stand-up, you need to be able to look inward. Monologue, however is rarely about the host. You won’t often see a late-night host tell a joke about their own personal life. Late night monologue is EXTERNAL— it’s about “what’s in the news today”.  Stand-up is also written primarily through INSPIRATION.  Things have to happen to you in life; you need to experience things to write about them and for the jokes to sound personal. Late night monologue is written through PERSPIRATION. You will be allotted a certain amount of time each day on staff to write a number of monologue jokes, so you need to produce quickly. This will be covered and taught in class.
  2. 80-90% of all late-night monologue jokes consist of two or more distinctly separate ideas, tied together in a funny and unexpected way.  As a comic this may sound foreign— the idea of NOT trying to write funny— but in writing monologue, it is the wrong approach. Writing monologue is all about associating topics. That’s the gig-  find the topics that tie together in a funny and completely unexpected way, and the joke practically writes itself.  An idea for a monologue joke becomes an equation waiting to be solved. For example, here’s a joke I wrote recently, based on the synopsis of an upcoming movie: 

“Liam Neeson is starring in a new movie where he’s stuck in a car for the entire two hours. It’s called, “Driving To LAX”. 
Here’s one from a few months ago, based on a George Santos statement:  “George Santos said he acted on “Hannah Montana”.  In case you’re not familiar with the character of Hannah Montana, she’s a young girl with an alter ego, living a double life in which she’s able to make everyone believe someone she’s not.  

-No; wait.  I’m sorry.  That’s George Santos.”

Again, another joke written through pure association.  When I read the plot synopsis for Hannah Montana, the parallel to Santos’ life seemed obvious.  Then it was just a matter of picking the right words to bear out my point.  I did not try to ‘think’ of a funny punchline.  I just free-associated and linked ‘handles’.

When I read about the plot of the Liam Neeson movie-  “…stuck in a car for the entire two hours”, it made me think of traffic. When I thought of traffic, I thought of driving on the 405 to LAX.  So, all I did was ASSOCIATE TOPICS, the bit ‘popped out’, and the rest was just ‘shaping’ the joke. Not once do I ever ask myself, “What would be a funny punchline?”, because that approach doesn’t work. Here’s another joke I wrote at Thanksgiving time:

“Butterball has a turkey hotline. I guess turkeys get depressed, too.”  

When I saw an ad about Butterball’s turkey hotline, my first thought was, “It sounds like turkeys are making phone calls.” Then, I free-associated and connected it with the “suicide hotline”. After that, the joke was essentially done, without any heavy lifting. Purely written through association.  To stand-ups, it can be a new way of approaching writing, and one that’s very formulaic (which as comics, we try to stay away from!)  -Keep in mind, if you’re formulaic in stand-up, it usually means ‘hacky’. But in late night, you MUST be formulaic.  There’s a musicality to late night, a language with its own rhythm, and it’s the most concise joke-writing there is. So, this class will not only help you with late-night writing, but with EVERYTHING you write. An extra “and” or an “or” in stand-up probably won’t make or break the joke, but in late night monologue, it can absolutely make all the difference in the world. It’s crystalizing jokes down to their simplest and purest form. Notice the Butterball joke is two sentences and yet less than one line, and the Neeson joke is only a line-and-a-half. Which brings me to my next tip:

  1. Monologue jokes, for the most part, should be THREE LINES OR LESS on the printed page. The host may go off on a tangent, and turn your joke into more than three lines, but that’s their call. They like to see jokes short, in your original submission. Again, this information is not in any book; this is purely based on personal experience in late night.
  1. You are writing jokes mean to be spoken, not read. Therefore, you sentences need to be colloquial, so it sounds like the host is merely talking. Watch out for using vocabulary that’s “news speak”, or sounds like a word you’d read in an article, rather than a word someone would use in conversation.
  1. Whenever possible, stay away from wordplay and puns. ESPECIALLY puns.  If you’re a comic, you know puns get groans. Late night hosts performing for millions don’t want groans; they want laughs. Create SITUATIONAL and VISUAL comedy, or, as my former boss, Dave Letterman would say, “Paint the word picture!”  For example, after a NYC article appeared about how brazen NY rats were getting, Letterman did this joke:   

“These New York rats are brazen.  Earlier today, I saw one in Rupert’s Deli, climbing down a hanging salami with a knife in its teeth”. 

That joke doesn’t even have the typical surprising punchline, but it’s so damned visually strong, it doesn’t matter!  It’s all about creating strong imagery.

  1. If you’re submitting a packet to a NETWORK late night talk show, stay away from what I call “first date subjects”.  I am constantly shocked when I see some of the jokes submitted in network talk, that never in a million years would be done on the air.  This isn’t good.  It’s a sign to the show’s reader that you don’t watch much late night and don’t take it very seriously, and again, will likely get your packet tossed.  Once you HAVE the job, don’t be afraid to submit anything, no matter how controversial!  But in your packet, NEVER have anything rejected because of content; that’s the one thing that’s within your control (whereas how ‘funny’ the packet is, is to a degree, subjective).

I would identify “first date subjects” to stay away from, jokes based on:  “Death, disease, sexual orientation, race and religion.”   

  1.  In monologue jokes, the set-up MUST CONTAIN THE ESSENTIAL INFORMATION THE PUNCH WILL ADDRESS, at the END of the sentence.  Why?  Because your jokes should ALWAYS end on a punch WORD or two, which will be at the very end of your jokes.  If you tip your joke early, or make your entire punchline the joke, it will not work the way you’d like it to.  The bottom has to drop out at the end of the line.  That sudden surprise is what generates the biggest laughs.   Think of the old stand-up joke:   “When I die, I want to go like my grandfather went, peacefully and in his sleep.  -Not like the folks screaming their heads off on his bus.”

In this case, “bus” in the punch word, and comes last.  We don’t see it coming, and it’s the sudden surprise than generates the laughter.

In summation; if you’re a comedy writer, this is the quickest and easiest route into television. You just need to learn the formulas and techniques to writing the perfect monologue joke, in addition to knowing what not to do that can potentially lose you the job.

I can’t tell you how many former students first approached me after submitting to the NBC Late Night Writers Workshop, after not getting the call. They then take this class, and say to me, “I wish I had known all this stuff before I submitted.”  This is a way for you to know ALL the “stuff” you need to know to land the gig and keep it. Take it from a 5-time Emmy nominee, former head writer of numerous talk shows and the guy who read submission packets.

Originally from New York City, Gabe Abelson holds a BA in Drama from Tisch School of the Arts at New York University where he studied with acting guru Lee Strasberg. After his success in booking a number of stage roles and television commercials after college, Abelson decided to pursue his real love… stand-up comedy.
A sought-after comedian, he toured the world for over a decade before being offered the role of Head Monologue Writer for “Late Show with David Letterman” (CBS). Within five years, he received five Emmy Award nominations and three Writers Guild Awards. He is a member of the Writer’s Guild of America) and SAG/AFTRA.
After his tenure at Letterman, Gabe relocated to Los Angeles to write for several network late-night shows, including “Politically Incorrect with Bill Maher” (ABC), “The Tonight Show with Jay Leno” (NBC) for which he also wrote, produced and directed segments and “The Late, Late Show with Craig Kilborn” (CBS). In addition, he was Producer and head writer for “The Tom Green Show” (MTV), Writer/Producer on the pilot of “Lopez Tonight” (TBS) and Consulting Producer for “Pop-Up Video” (VH1).
Gabe served as the Head Writer for the Golden Trailer Awards for 2000, 2004, 2007, 2009, and 2010 as well as the Head Writer for the 2004 Canada Walk of Fame. He also wrote for the 2012 Gracie Awards.
He has written for sitting U.S. presidents George W. Bush and Bill Clinton, as well as notables Robert DeNiro and Nathan Lane. Gabe has also written for and performed with Hollywood film and tv celebrities Ray Romano, Chris Rock, Jerry Seinfeld, Kevin James, Bill Hicks, Sam Kinison, Adam Sandler, Jerry Seinfeld, Kevin/or James, Dave Chappelle, Brad Garrett, Rita Rudner, Eddie Murphy, Wanda Sykes, George Lopez, Richard Jeni, Ellen DeGeneres, Sarah Silverman and Jon Stewart.
He has appeared as a performer on “Late Night With Conan O’Brien” (NBC) “Late Show with David Letterman” (CBS), MTV’s “Half-Hour Comedy Hour”, “Comedy On The Road” (A&E), “The Today Show” (NBC), “Caroline’s Comedy Hour” (A&E) and Comedy Central.
Gabe has been a master writing coach and instructor of both stand-up and late-night television comedy for over 35 years, affiliated with New York City’s Manhattan PunchLine Theater (Broadway’s stage devoted solely to comedy) to Flappers Comedy Club in Los Angeles. Many of Gabe’s former students now have successful careers in late night network talk show writing, sitcom writing and stand-up comedy, including Gary Greenburg, long-time head writer and executive producer of “Jimmy Kimmel Live”. Another of Gabe’s former Flappers students, Travon Free, won the Academy Award for “Best Short Subject” in 2021, in addition to several Emmys he received while writing for The Daily Show. On almost every late night talk show staff, you will find one of Gabe’s former students.
Gabe recently sold an animated feature to Dreamworks in conjunction with producer Jason Koornick (“Next” with Nic Cage), Universal Press Syndicate and Andrews McMeel publishing.
Gabe produced Comedy Central’s “Bar Mitzvah Bash Special”, Nickelodeon’s “Edgar and Ellen”, Discovery’s “Josh Gates Tonight”, Planet Green’s “Go for the Green”, FOX’s “Beyond Twisted”, GSN’s “Instant Recall”, Direct TV’s “Supreme Court of Comedy”, AXS TV’s “Tom Green Live”, FUSE’s “Skee-TV”, Adult Swim’s “The Tom Green Flash Mob Talk Show” and FUBO TV’ss “Call It a Night with Julie Stewart-Binks”.

Leave a Reply