Happy Monday, guys! Today I’m sharing a post from my dear friend Jon DeWalt, who also happens to be a brilliant comedian and writer for NBC’s Undateable (I think if you asked him what he does, though, he would probably say “Be a friend to Annie” first, which is why I ranked his titles in this order.) This piece originally appeared on his blog several months ago, but I wanted to share it as a follow-up to his wife and writing partner Allison Bosma’s hilarious post on her audition from hell that appeared on Heels in the Hills last week. Jon’s story is equally inspiring for all of us dreamers…
SUCCESS FROM FAILURE
by Jon DeWalt
Growing up, I always dreamt of doing comedy for a living. In any form possible. To make a living just from comedy – no “normal” job. That was the extent of my dream; don’t need to be famous or crazy rich – just wanted to be a “professional” on whatever level I could. Eleven years into my full-time pursuit of this goal, I became a staff-writer for NBC’s “Undateable” (my rise has been quite meteoric – Just a shade over a decade to reach entry level!). And as if the job weren’t enough, I get to do the show with my wife, some of our best friends and great head-writers to learn from and grow under. So this show has been a dream come true on many levels.
My writing partner/wife, Allison, hard at work.
Show night with Brent and visiting family.
My best friend/former YouTube sketch partner, Rick, as Burski.
As we begin writing our third season (this season we’ll air every episode LIVE; the only live sitcom on earth… so that’s something!), I’ve been looking back at my three years living this “dream.” Which has made me think a lot about the dream I never accomplished. The dream I failed at.
I remember one powerful monologue by Adsit featured him ranting about how Blockbuster (the 90’s!) was limiting people’s freedom of speech and censoring what videos could be rented. To voice his rebellion, he made every audience member pass their Blockbuster cards to him on stage. Adsit would proceed to take everyone’s card and cut them up while they watched. For real. Their cards were really destroyed. So, the audience paid money to come to this show and left without a Blockbuster membership because Scott was pissed at their policy. I loved that. On the way home, I thought “Some people probably loved that he cut up their card and will never go to Blockbuster again. But the people who didn’t get it, or who didn’t care about his stance, had to go into their local Blockbuster and explain to the teenager working the register why they need a new one printed.”
“No, I didn’t lose it. A guy at a comedy theater in the city cut it up. No, he didn’t take it from me. I gave it to him. Well, because everyone gave him their card. Because he asked us to! What did people do when he destroyed our cards? I don’t know, they laughed I guess. Look, just give me a new card!” — In it’s most basic sense, that’s what comedy is to me. Not just the show. But the scene of the middle-aged Dad having to go get a new card that played in my mind. The aftermath of the show. To you all, Scott Adsit might always be “That guy who’s in most of the 30 Rock episodes as Liz Lemon’s Producer.” But to me, he’ll forever be Blockbuster Card Guy.
Here’s a photo of my favorite scene from their show “Paradigm Lost” called “Gargoyle Boy:”
The woman with the short, sensible, haircut turned out to be one of the strongest writers in all of comedy.
All I wanted to do was be one of them. I wanted to wear a black suit and tie and be on that stage and be loud, smart and funny. I wanted to have cast photos like these:
So, I went for it. From age 17-23 I was at The Second City and iO Theaters in Chicago every day and night. For classes, to perform in shows and to go see shows that I had already seen 20+ times. Even when I went to college at Illinois State for a year, I would take a train 3 hours home, then drive one hour to the city for improv class. Every weekend. This led to me falling asleep from exhaustion during the drive home and rear ending a family (The Grandma started acting like her neck hurt, but I knew that bitch was faking.) Everyone was okay, my car was totalled and I dropped out of college to move to Chicago to pursue comedy full time! A parent’s dream! Without school to slow me down, improv and sketch comedy became a 7-day a week affair.
When you’re an improv nerd in the training center and performing shows, you’re very much a cult member, as Tina Fey describes in her book, “Bossypants”. Anytime you pay-to-play for small club shows while also taking (expensive) classes about “playing make believe” and hope to turn it into a full time career; complete with pension, medical/dental and a healthy income – in real world terms, you’re in some fuckin’ trouble.
I was in some fuckin’ trouble and didn’t even know it.
Performing with my first House Team at iO Chicago. 2007. Wearing the black suit like a total poser should.
With my video-sketch group. Pre-YouTube, Pre-Lazy Sunday. I actually stand by the comedy of this Power Ranger parody.
Chicago: A beautiful place to tape a shitty web video.
As you can see by the above photos… I was doing preeeetttyyy well! I made a House Team at iO, which was a bigger deal to us back then than having a baby, I created what I think was the first Chicago based digital sketch group, pre-YouTube, pre-Lonely Island (“pre-Lonely Island on SNL” that is… What I did was a direct rip off of their LA-based website trio at the time. Without any of the sophistication, charm, business savy or success! Jorma is still my fav all-time, btw).
I was in trouble because I was young, incredibly energetic (read: spazz) and “good enough for a kid.” If average is 5 and “Oh my God that dude is gonna make it!” is 10, then I was a solid 5-and-a-half. But in my early twenties, living alone in the city and “finally doing real comedy (dork)!” – I thought I was an 11. “This is it, baby!” Anytime you’re a 5.5 who acts like an 11, it’s not great.
In hindsight, I now know what I lacked was perspective, a point of view and anything important to say. I was a kid who did comedy for comedy’s sake inspired by comedy. I had no life experiences, no fire. I was the annoying 19 year old you hate in your improv class, but with worse hair, worse clothes and a louder laugh. I had no self awareness. That’s why my favorite improvisor my own age back then (and still) was a woman who had all those tools despite our youth, Lauren Lapkus. I was a big fan of hers right away and the silly thing is I thought we were on the same level. I did not see that her comedy (& many other people’s) was more sophisticated than mine. When she did a crazy sketch, she was making fun of something or showcasing her character range. When I did a crazy sketch, it was because I wanted to wear a children’s Power Ranger costume in a public park (see above photo). So I did what any young male improvisor who thinks a woman is funny would do: I asked her on a date over AOL Instant Messenger. She instantly said, “Literally never.” & we’ve been friends ever since.
iO Chicago with Lauren. We’re probably 20 here. I regret that my shirt is buttoned to the top.
Unaware of myself, I kept plugging along doing work that ranged from bad, to average to kind of fun – all while having a limited understanding of who I was or how to use comedy. Then came my chance! Over the next six months, I had two Second City auditions and the woman in charge of hiring talent came and saw my show at iO (this was also more important to us than having a baby). I went to Detroit to audition for Second City Detroit, I bombed in a pretty impressive way, like, it’s hard to do that bad. I did a scene with Sam Richardson (who is now killing it on “Veep”) and basically watched him do amazing work as if I was in the audience. He got the job and was on his way. I went back to Chicago knowing I choked. A few months later, the VIP Second City gatekeeper came to see me at iO and our show was… a show, technically, but certainly lacked for jokes, range, skills — anything useful to a woman that hired for The Second City. Then, I auditioned in Chicago for her officially. I walked in and she said, “Hi, Jon!” — and in my young ego filled head (read: cocky spazz) I KNEW that I had it. Done deal. Hell, she probably watched my latest web-video gem where my friend and I kept throwing pies at each other! I promptly did average scene work for her and never heard back.
A few months later, an opportunity to temporarily join famed Amsterdam comedy troupe, Boom Chicago (as a video editor/writer mind you, not a real cast member because… I’m a 5.5 who thinks he’s an 11) came up and I took it. I travelled, had some new experiences and when the gig ended I decided I was already uprooted; I was going to move to LA. The young ego said, “Dude, I want to make it! I don’t want to wait until I’m thirty to get hired for Second City. With YouTube and all the LA based theaters I need to get in the game now!” The unspoken truth I knew was, “You can’t sing, you have zero impressions and can’t do characters. You’re not going to make it in Chicago.”
Dream over. I would never get to wear a black suit and tie and cut up the audiences’ video rental memberships. I would not have black and white cast photos hanging in the Second City lobby. My legacy would be wearing an ill-fitted black suit and sambas at iO (where you don’t wear suits because it’s not Second City), and having hyper-young-guy-scenes where I yell at people like this one:
“Steamrollin’ in Chi-Town!”
But for all the raggin’ on myself I’m doing, the one thing I did right was know that it wasn’t the end of the world. If it wasn’t going to be the traditional “Second City to SNL to Movie Star!” path that all the legends had taken, I was going to find another way. In improv, the first thing you learn is to “yes and” – which just means agree to whatever your scene partner establishes, then add to it. As cheesy as it sounds, I have always been able to apply that philosophy to life in general. When life said, “Hey it’s not gonna happen this way.” I said, “You’re right. Let’s try this next.”
LA brought what I needed. Life experiences. I swept hair at an awful barbershop for money and did extra work where I met the hilariously unique Rick Glassman, who changed my life. He took me around the stand-up clubs & we started a new video-sketch team – only this time, we had opinions in our goofy comedy; a voice was starting to develop. Through Rick, I met a stand-up named Brent Morin, who like Lauren in improv, was the best at what he did at our age. Brent was a story teller, not just a joke guy. He would tell a 6-minute, joke filled story that built upon itself and paid off with a big climax, which helped change the way I looked at things. After hanging around them for a while, I started to get on stage myself as a stand-up comedian. I loved writing because if something worked, you get to keep it and perfect it as opposed to improv where it goes away forever. I started to apply my obsessive personality to writing, getting my hands on scripts of “The Office” and teaching myself how TV writing worked by analyzing scene lengths, page counts, how stories are structured, etc. I went out with Rick, Brent and the boys and did stand-up every night. And we had some fun.
With Rick at The Comedy Store in 2010.
At the mall with Rick and Brent.
My second video-sketch group. YouTube’s “That Guy & His Friend.”
Singing with Brent and Jason in San Diego. The joke is that I’m very tone deaf.
The biggest life experience LA had to offer came when a girl I met once in Chicago came to visit. She wanted to have dinner with me to talk about the transition from Chicago to LA. When I saw her that night, I knew I had to marry her. Luckily, that is one dream I did not fail. You know what they say: “The one thing an annoying-as-fuck-hyper-kid-who-needs-to-chill-out-and-become-a-real-person needs, is a good woman.” That was Allison.
Pics at The Grove like all new couples do.
I regret my “Neo Matrix Replica” shades. eBay :(
Our first official date.
Allison grounded me as a person, challenged me and forced me to grow up (a little). And as luck would have it, she was hilarious and better than me at acting and writing! I equate our relationship as comedy partners to Shaq-Kobe. Where I’m the Kobe: For me to be any good, I have to obsess. Tunnel vision, can’t focus on anything else, space out during small talk because I’m thinking about a scene, etc. Allison is the Shaq: She can show up with little to no prep time, look at a scene, think for a minute and offer the perfect tweaks, additions, cuts and new jokes. Like Shaq, she is a monster (thankfully a much tinier one). Throw her the ball in the paint and get the fuck out of the way.
I remember writing our first TV script together and I thought I was the big shot since I “taught myself structure.” I would try to teach her about where stuff should go and she would look at me like I was an idiot and say, “No. You can’t end this multi camera sitcom with a voice over montage because it’s not a single cam. It’s a multi cam. It makes no sense with the style we established in the first two acts.” To which I flipped through my notes and said, “Yeah, but… uh, I know, so… What’s for dinner?” Allison is the opposite of me in a lot of ways and makes up for a lot of my glaring holes that were happily exposed in Chicago.
There are two types of people who make it in comedy. Either you’re a phenom-megastar and it happens right away for you, or you’re a grinder who’s always working on something, trying to get better and trying to break in. To us grinders; passion, obsession and work ethic are the key ingredients. But perhaps none are as important than luck. That’s why this career is so hard to get started, you can’t control luck. Also, when you do get lucky, you better be ready. Because who knows if you’ll get another shot.
Our luck came when Brent was starting to blow up and caught the interest of “TV’s Bill Lawrence” – The Hollywood big shot responsible for many shows including “Scrubs,” which Rick and I were randomly binging on Netflix that month. We had no idea we were about to meet the guy whose name appears in the opening credits X-Ray shot. Bill came to see Brent at the Hollywood Improv and as luck would have it, Rick and I were also on the bill that night and Allison randomly decided to come watch us for the 100th time. We ended up hanging out with Bill and his right-hand man until midnight in the lobby and a year or so later, all four of us worked at “Undateable.” I had reached my goal. By following my own weird, less glamorous, path. My mom never prayed harder than the “Thank you, Lord’s” she sent out that week.
In the writers’ room with Bae.
“Real life Entourage” with “Undateable” creator, Adam & Supervising Producer, Craig.
The second most famous NBC sitcom bar. Or third? Whatever.
I guess what I’m trying to say to all the comedy grinders out there is: Be ready to adapt when your strengths finally reveal themselves. If I had stayed in Chicago chasing a dream I didn’t have the skill set for, I would never find work in the industry I do have a skill set for. And I never would have met my wife and some of my best friends.
Back in the day, the path for Chicagoans in comedy was clear: Improv->Second City->SNL->Movie Star. If you can do that path, great! Enjoy it you lucky bastard, I can’t wait to see your black and white photo in the lobby. Failure showed me that other options existed that I never even thought about. So please be honest with yourself. If you find yourself in a rut where no “forward motion” has happened in a long time, it’s time to explore something else. You might find something you’re better suited for and are much better at! Remember this is a dream where far less than %2 of the people aspiring to get it actually have a sustainable long-term career. So if you’ve been doing your thing for years and years and stalled, don’t be afraid to change it up.
What’s exciting to me these days is as I said earlier, it took me eleven years to reach entry level. This is just entry level. That’s amazing. Who knows what the next eleven years will bring (assuming I don’t get fired and have to restart my dog walking business that is). And all it took to set me on the right track was a little failure. Wonderful, painful, tear-filled failure! Anywhere I get in Hollywood, all comes from that first failed dream. And while not having those classic Carell-Colbert-Fey-Farley cast photos will forever be a regret of mine, it’s as big an honor, maybe even moreso, that I do have these ones:
The boys with Bill Lawrence & Adam Sztykiel. Season 1 finale.
Most of the season 2 writing staff.
Nice suit, nerd. #blessed
With the theme of “accomplishing your dream but not in the way you originally envisioned,” I think it is so appropriate that I work on the OTHER live weekly comedy show on NBC. So I get to close this by saying, “Live, from Burbank, it’s Friday Night!”