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How A Rising Comedian Is Turning Sketch Comedy Into Short Film Gold

The Innovative Short Films of Tim Dillon (and what you can learn from them)

Comedian Tim Dillon has had quite a 2020. He’s been on Joe Rogan’s extremely popular podcast several times, runs a podcast of his own that clocks several hundred thousand views per episode and still finds time to tour (when COVID restrictions allow).

But perhaps the most interesting content he’s creating doesn’t fit a traditional form or structure. We’re talking about his inventive short sketch videos, also on his YouTube page. Usually 1–3 minutes long, these short films match his aggressive, controversial and politically-charged comedy style. The topics he covers range widely, from popular conspiracy theories to the inanity of the contemporary news cycle to whatever’s hitting the zeitgeist, but they always come from Tim’s signature, bizarro and hilarious vision.

Let’s explore what you can learn from Tim Dillon’s short sketch videos and how you can apply it to your own short form content.

Tie Short Film Content Back Into Your Larger Universe

Every Tim Dillon short acts as a prelude, followup or companion to his podcast and standup content.

We all know about the Marvel Cinematic Universe, the brainchild of Disney and Marvel that has spawned several dozen film and television projects that all interlink and reflect the same timeline.

But large universes don’t have to just come from big business. Rising comedians with an entrepreneurial spirit — like Dillon — are finding interesting ways to tie shorter, more viral-ready content back into the flagship content (Dillon’s podcast and standup shows).

For example, during Dillon’s stint back in the East Coast (where he is from) earlier this year, he created several videos around New York, pulling from his own history there and from current events. In “New York Is Back, Baby!”, Dillon explores the rapidly-changing street life of the Big Apple following COVID and the summer’s Black Lives Matter protest in a way only Dillon could.

Similarly, in “JFK Tour Guide Tells All,” Dillon plays a conspiracy-crazed New York City bus tour guide. While great comedy (and frightening) on its own, the video only grows in your estimation if you follow Dillon and know that he used to be a New York bus tour guide and was very into conspiracy culture.

And we haven’t even mentioned all of the holiday or event-themed videos Tim puts together — always with a sadistically humorous twist. The truly adventurous could use Dillon’s videos as a time capsule, looking back at the year that was 2020 through the eyes of Dillon’s comedic vision. Just one more way to take in this content and make it valuable to his growing audience.

Blending fact and fiction in this way rewards those who are the biggest fans, and incentivizes those who aren’t yet to get in on the Dillon craze (either by subscribing, joining his Patreon or buying tickets to a future show).

Create Infinite Versions Of Your Persona (For Infinite Possibilities)

Tim’s always got a new character or persona up his sleeve.

Lots of YouTube shows, podcasts and other short form content creation rely on the same formula time after time. There’s a certain level of comfort in revisiting characters where they are (that’s why we have sitcoms after all), but to make your short form content stand out in 2020, the status quo just will not do.

In the case of Tim Dillon’s short film content on YouTube, he makes sure two things always happen:

  • The content is centered on him.
  • He’s almost never playing himself.

The first point is important, because brand recognition certainly matters, especially when you’re going it on your own as a comedian (or as a filmmaker or as any kind of storyteller). The second point is even more crucial, though. There’s a version of these videos where Dillon could just play himself caught up in all of these goofy scenarios, but either through a little postproduction, costume changes or new dialects and mannerisms, Dillon explores all walks of life through his own embodied self.

Sometimes he plays real people (in very heightened ways) such as the controversial Meghan McCain and Ghislaine Maxwell skits. Sometimes he plays off of familiar types, like opportunistic Los Angeles realtors or enthusiastic Bernie Sanders supporters. He finds a way to poke fun of everyone by becoming them and injecting it with a brand of humor only he can consistently deliver.

Think about your own characters or personas you’re trying to create with short content. How can you mix it up each time? If not a new character, what about a new location or a new structure and formula? Notice that no two Tim Dillon shorts ever feel the same, not just in content but in structure and form.

Be Bold (Then Be Ready To Alienate Some People)

Just in time for election season, Tim Dillon made a controversial short about a hypothetical Nevada poll worker. It alienated some but intrigued many others.

This is where Tim Dillon really shines in the comedy world. He’s willing to take unpopular stances, call people out and leave no topic uncovered. While it works great in his standup bits and through the podcast, this try-anything-once attitude really makes for memorable (and viral) short film content.

Whether it’s a creepy Gates Foundation lab scientist type he plays for a Halloween take on vaccines or a drugged-up Nevada poll worker for a video that came out the week of the election, Dillon does not play it safe. While that understandably creates a lot of people who are going to opt out, it will also have the second effect of enticing a more rabid and committed fanbase. Because usually the more bold you are with your content, the more unique your work will be.

Now, when it comes to your own content being unique, it isn’t just about being controversial. There’s several different ways to stand out from the crowd. Find the one you’re comfortable with, don’t compromise on your vision for a hypothetical broad audience that may never find you anyways, and instead play to the people who will love what you do and follow you for years to come.

You can watch all of Tim Dillon’s shorts right here.




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The first online platform for award-winning short films. Start watching today also available in the AppStore and Google Play.

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