Leesa Dean: Adventures of a Web Series Newbie – Chapter 15


by Lessa Dean

Really busy week. Not going out as much (to panels, workshops, etc.) but heavily working on a new top secret project that I’ll be able to share in a few months. And between that, tweaking Episode 8 of Chilltown (which launches next week!), doing the radio shows (the Lele segments plus three new interviews this week, including one on HipHopHeadz which really was a ton of fun.)

Something kept cropping up during the interviews: I got asked how I broke into writing. Not the web arena, but writing in general.

I fell into it. Definitely was not planned. It started with games.

I wasn’t a gamer, but really loved the immersive ones. Myst was my favorite. And I thought I had a great idea for one. A neighbor’s girlfriend worked at Paramount and over drinks told me what I needed to put together to pitch. It all started with a script.

Since I had never written one, I asked a journalist whose writing I admired if he wanted to be involved. He said, “Sure! For $7,000.” Where he came up with that number, I’ll never know, but $7,000 was way more than I had at the time. In a knee-jerk reaction I said, “Yeah, well maybe I’ll do it myself then. ” In parting, he left me with this advice: “Writing’s the easy part. Selling it is what separates the men from the boys.”

I thought about it. I actually didn’t seem like that bad of an idea. The worst thing that could happen was, it would suck and I’d move on. I bought a book on standard script formatting, got a copy of Final Draft and winged it. I also came up with really in-depth character descriptions. All the characters were very cartoony. I always loved animation and looking back at it, realize that’s what I wanted to do.

At the time, a friend who was still in college got an internship at MTV and moved back to the city. We got together for dinner and I told him all about my project. Even showed him some of what I was working on. He said, “You know, this shouldn’t be a game. This should be a tv show.” He set up a meeting with his brand new boss. She had a pretty big position in business affairs and if she liked it, could set something up with someone who might buy it.

She looked everything over and said, “These are the best developed characters I’ve seen in a long time. But you need to have a pilot script to show him. Can you do that?” I asked how long it should be. “Five minutes.”

I didn’t know where to begin so I went to The Drama Book Shop, asked to speak to a salesperson and the guy behind the counter pointed out a woman who was kinda rocking the Che Guevera look: all khaki fatigues, brown tinted sunglasses, beret. She was outside near the door, feverishly sucking on a cigarette and furtively looking around.  An omen?

I told her my story and she said, “You know, I’m a director. In the DGA. And I don’t wanna scare you, but it’s tough out there for women in this business. Even writers. Wanna know why I’m working here? I just came back from a shoot in Florida. A commercial. I was supposed to be the ADA and the director kept turning to me and saying, ‘Dear, could you bring me a coffee? Dear, could you go get something from my trailer? Dear, would you mind moving that chair over there?’ I finally looked at him and said, ‘Do I look like I have a pair of fucking antlers?!?!’ and quit!”


But she did recommend three books: Linda Seger’s How to Make a Good Script Great, John Gardner’s The Art of Fiction and DiMaggio’s How to Write for Television.

I was off to a start.

Author: ChilltownTV

I'm primarily a writer. Sold a few series to tv networks and production companies but never had anything get on the air. So I taught myself how to animate and completed 3 digital series, launching two. The first, Chilltown has been named one of "Five Web Series That Should Be on Your Radar" by ABCNews/Univision and a "Show to Watch" by Tubefilter. The second, Lele's Ratchet Advice Show, garnered a fanatic cult following. As a result, I now do Lele's 60 Second Wrap Up, a weekly comedic entertainment report (which I write & perform) that airs on urban radio stations Rhythm 105.9fm and the Just Wake Up Morning Show on WWRNfm.

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