Funny on Purpose

1. Comedy Writing: Problem-Solving with a Twist

Most of writing, then, is problem solving.

Facing the Blank Page. Writing comedy is like standing before oblivion, a daunting task of turning infinite possibilities into a finite form. It requires confronting the fear of failure and the potential for your work to be terrible. The writer must siphon out what is in their brain and shape it into something that can be understood by others, and to do that you have to concentrate really, really hard.

Disassembling and Reassembling. The writing process involves disassembling something that doesn't yet exist and putting it back together without instructions. The writer must describe what they see in their mind's eye, giving it a beginning, middle, and end, while also making it funny. This requires creative energy, concentration, perseverance, and a rebellion against reality itself.

Subverting Expectations. To write a funny sketch, one must subvert the momentum of millennia and stake a claim for human consciousness in the vast, thoughtless plane of existence. This involves taking familiar concepts and twisting them into something unexpected and humorous. The simplest definition for what makes something funny is "abnormality."

2. Comedy Partnerships: Trust, Morale, and a Shared Language

Who cares what the idea is? Let’s make the idea work.

The Power of Trust. The most important factor in a comedy partnership is having someone you can trust. You need someone you can rely on to tell you when your jokes are no good and to praise you when they are. You have to be able to give them your most precious possession—your imagination—and trust them to make it better.

Boosting Morale. Comedy writing can be emotionally draining, bringing you to the brink of self-immolation on an almost daily basis. Having someone who can talk you down from time to time and convince you that life is worth living is a valuable asset.

Creating a Shared Language. Working closely with someone allows you to form a compact language for creation. This language might make absolutely no sense to anyone else, yet there’s an efficiency to this kind of succinct, intuitive communication that allows concepts to be conveyed outside normal means.

3. Taste in Comedy: Balancing Edges and Offense

I can’t think of anything more offensive than a standup routine based on racism or misogyny—not only because this perpetuates ignorant, socially violent ideas, but because it’s boring.

Navigating the Outrage Industry. An entire industry of outrage has sprung up and thrived in the incubator of the Internet. Every few weeks, someone says or writes something that a vocal segment of the population finds offensive, and the rest of us are dragged into an intense, hateful, demi-debate.

Pushing Boundaries Responsibly. Comedy's role is to push the bounds of comfort and challenge authority. Without these principles, and an important and universal third principle, which is to smear the edges of tragedy with a shared sense of the absurd—one does not have comedy.

Context and Intent Matter. It’s about context and intent. Does your joke make a broader point about sexism, or is it just using those boring old tropes for an easy laugh? Are you taking a stand against racism, or are you just being racist? The first category is noble. The second is cowardly.

4. Web Writing: Brevity, Shareability, and Visuals

It has been said that there are more jokes written in one minute on the web today than were written in all of the twentieth century.

The Internet's Insatiable Appetite. The Internet seems to have an insatiable desire for more and more content, but historically it has not cared as much about quality. Most writing for the web is disposable; it often feels like putting a little sailboat on a river and watching it go over a waterfall, never to be seen again.

Key Elements for Online Success:

• Shortness: Don’t expect people to read anything online for more than one minute.
• Shareability: People are infinitely more likely to share something they’ve actually read.
• Visuals: Videos have to look interesting from the very beginning and create an environment that viewers can immediately understand.

Crafting Engaging Content. To stand a chance of being read, you’ve got to stay short. People should instantly get the joke. Do not make people work to understand your “concept.” Your concept should be the part that’s funny.

5. Sketch Comedy: Short, Sharp, and Subversive

A good sketch needs a good, solid, interesting concept. A great idea. And the sketch executes that idea perfectly.

The Essence of Sketch. Sketch may well be the purest form of comedy, but like that game Othello and probably a bunch of other stuff, it can take a lifetime to master. Sketches are short, tight, packed full of jokes (or one incredibly well-earned joke), and often grouped together as part of a larger show.

Key Elements of a Successful Sketch:

• Strong Concept: A good sketch needs a good, solid, interesting concept.
• Execution: The sketch executes that idea perfectly.
• Brevity: All sketches are essentially one premise, explored and stretched and taken to the farthest degree possible—in the shortest possible time.

Questions to Ask About Your Sketch:

• What’s funny about it?
• Is it grounded in reality?
• Can it be shorter?
• How does it sound out loud?
• What is the biggest joke?
• Is your sketch a sketch?

6. TV Writing: Experience, Collaboration, and Thick Skin

I’ve seen more writers fired for not shutting up than just about any other crime.

Getting Staffed. In TV, getting a job is called “getting staffed,” and staffs can change from season to season depending on any number of things, from job performance to ratings. Most comedy writers work on a bunch of different staffs throughout their career, though some find one they like and manage to stay there for years.

Navigating the Writers' Room. The writers’ room is TV’s inner sanctum, where ideas are born, changed, debated, and murdered. These are legendary places that very few people are ever allowed to see—special places that embody a weird alchemy of creativity, competition, camaraderie, and whiteboards.

Essential Skills for TV Writers:

• Pitching ideas effectively
• Brainstorming collaboratively
• Taking notes gracefully
• Writing quickly and efficiently

7. Book Writing: Idea, Agent, and a Solid Proposal

The Internet has become the proving ground for book ideas.

The Path to a Book Deal. Though the printed word was officially pronounced dead in 2009 at the age of 560, a small number of humorous books are still published each year. In fact, book writing remains an important part of the Comedy Person’s portfolio, be it in the form of memoirs, essays, instructional manuals, or plain old silliness.

Key Steps to Getting a Book Deal:

• Have an original and marketable idea
• Secure a reputable literary agent
• Craft a compelling book proposal
• Shop the proposal to publishers
• Negotiate and sign the book deal
• Write the book
• Promote the book

Crafting a Winning Proposal. Your proposal should be something you are proud of, something you are always updating and improving, because openings will come up unexpectedly—and so you, the unwitting potential comedy writer, will be asked to submit one with little or no notice.

8. Film Writing: Structure, Characters, and a Great Title

I wish I could tell you that I have all the answers, kid. That there’s some magic, secret recipe for making it big in Hollywood.

The Elusive Path to Screenwriting Success. I wish I could tell you that I have all the answers, kid. That there’s some magic, secret recipe for making it big in Hollywood. That all you need to do is rub the right lamp or suck the right peace pipe or have sex with the right metaphor and then, boom, you’re a successful comedy screenwriter with awards, money, respect, and a decent commute. But I can’t.

Essential Elements of a Comedy Screenplay:

• Strong Three-Act Structure: A clear beginning, middle, and end.
• Compelling Characters: Relatable, flawed, and funny.
• Great Title: Short, descriptive, and evocative.

Selling Your Screenplay. Writing the funniest screenplay of the last ten years is great, but selling it is even more greater because you get to make money. For instance, the WGA (Writers Guild of America) minimum payment for an original screenplay ranges from $70,000 to $130,000.

9. Standup Comedy: Honesty, Practice, and Community

My first year, I got fired from every job after the first night.

The Standup Journey. For generations, standup comedians have been defined by a kind of tragic, star-crossed relationship with fame and their chosen career: grizzled, jaded, cynical, and unable to exist in a society that has no convenient place for them.

Key Elements for Standup Success:

• Honesty: Be true to yourself and your experiences.
• Practice: Hone your craft through constant performance.
• Community: Support and learn from other comedians.

Dealing with Stage Fright. There’s no cure for stage fright, but there doesn’t need to be. Feeling scared and worried that you are a fake and have no reason to be there, that everyone is going to hate you, that you will never be as good as you want to be, and then stepping in front of the microphone and performing anyway is enough.

10. Improv: Agreement, Support, and Spontaneity

When we started writing Monty Python and the Holy Grail, the only thing we had at first was the bit about the coconuts.

The Essence of Improv. Improv first took shape in Chicago in the 1950s, and its influence can today be seen everywhere, from the influx of Second City and Upright Citizens Brigade (UCB) alumni like Bill Murray, Tina Fey, Stephen Colbert, and Amy Poehler to the improvised style of Judd Apatow’s films and Larry David’s Curb Your Enthusiasm.

Key Principles of Improv:

• "Yes, and": Accept and build upon what others create.
• Support: Make your scene partners look good.
• Spontaneity: Embrace the unexpected and trust your instincts.

The Value of Improv Training. Improv offers things that no other training, comedy or otherwise, offers. It forces you to cultivate what is happening onstage without prejudice, meaning that you can’t steer the conversation into a certain direction or avoid awkwardness, as you would in real life.

11. Music: Style, Performance, and Distribution

I can shamelessly leech onto whatever new musical trend comes along, and that doesn’t make me a sellout or a poseur . . . that just makes me Weird Al!

The World of Comedic Music. When I was a kid, I had a bootleg cassette tape of Dr. Demento’s top songs of 1987, and I played that goddamn thing into the dirt. It was a mix of parody, goofiness, and straight up original weird I’d never heard before. It felt like a rare and special prize.

Key Elements for Success in Comedic Music:

• Define Your Style: Determine your unique comedic voice.
• Master Performance: Hone your stage presence and musical skills.
• Embrace Distribution: Utilize online platforms and live shows.

The Business of Comedy Music. The biggest obstacle for comedic musicians is getting people to see and/or hear you. Maybe you don’t want to haul your glockenspiel to every coffee house open mic, but there’s really no substitute for a live show.

12. On-Camera: Authenticity, Preparation, and Connection

If someone could invent a way to get a mic on a shirt without having to stick it to my chest and ripping my chest hair out, that’d be great.

The Power of On-Camera Performance. The vast majority of the comedy seen by the American people will be on TV or film, and yet only the teeniest percentage of the world’s already small proportion of funny people ever get to appear on camera.

Key Elements for On-Camera Success:

• Authenticity: Be yourself and connect with the material.
• Preparation: Know your lines and understand the scene.
• Connection: Build rapport with the cast and crew.

Performing for Your Editor. After you have performed for the camera—be it for a small-scale web video or a major motion picture—that performance will be cut up, moved around, and perhaps augmented with visual effects. All of that stuff, unless you are Tom Cruise (OMG, are you?), is out of your hands.

Last updated: February 14, 2025