Today is the 30th Anniversary of My Debut in Stand Up. Or How I've Spent 3 Decades at the Bottom of Showbusiness

[Note: I don't have a photo from the early days. Back then you had to stand perfectly still while the photographer went under the hood, focused the lenses and held the aperture open. This recent, unfocused one will have to do.]

September 3, 1990. Labor Day night. 30 years ago today. It remains one of the most significant days in my life because I took the stage at a comedy club for the first time and launched a career that continues to this day. Which is to say, it continued to just before everything got shut down in early March and cancelled every show on my calendar through the end of the year. And since for all we know I may never do another one, it seems like as good a time as any to indulge myself and maybe give you some insight into what being a semi-working comic is all about. 

For starters, I didn't start out wanting to get into comedy. The first time someone suggested I do it, they might as well have told me I should try being a test pilot or fight oil well fires or a bomb disposal expert. All sound like cool jobs that would impress girls in bars a lot more than telling them what I really did for work, but way too dangerous for my blood. I preferred a quiet life of obscure mediocrity where failure would kill me. 

But at some point, enough people who didn't know one another either asked if I was a comic or told me I should try it that I at least started thinking about embracing the danger. I checked out a few Open Mic shows featuring new and first time comics and had the same reaction as first time I saw my friends golf when I'd never done it. Which was "I can suck as bad as that. The only difference is that guy is out there taking hacks and having fun and I'm not. Eventually I just got to a point where I was bored with playing it safe and was more afraid of never taking the chance than I was of trying and failing. 

To repeat something I've heard a hundred comics say in a thousand interviews: I never considered myself to be funny. I'm the youngest of five, my brothers and sister are all funny. And in our house you had to have some chops in order be heard, noticed, paid attention to or fed. Easily 90% of the guys I hung out with - and still do - are objectively funnier than me. If anyone was suggesting I get into the business, I'm convinced it was because I was able to talk like a stand up comic. The storytelling, setting up a joke and paying it off, the rhythm, the cadence, the timing, certain beats you want to hit and so on. I could organize funny ideas into coherent thoughts as opposed to simply being hilarious the way other guys are.

Probably because I spent way more time watching comics on TV and memorizing classic albums from greats like George Carlin, Richard Pryor and Rodney Dangerfield than any healthy kid probably should have. To me, a great monologue is like a song. It's carefully written with precision. A beginning, a middle, an end and sometimes a call back. And with repeated listenings you can keep getting more out of it. And while I wasn't lifting great comics' bits directly, I figured out how to present ideas the way they did. And as I went through school I went from being a fairly quiet kid to someone who could make the cool kids laugh and become part of their circle. 

Anyway, that first Open Mic show was simply a matter of calling one of the clubs and getting put on the list. I chose the legendary Nick's Comedy Stop in Boston's theater district. Then it was a massive barn of a place where I once shook hands with Jay Leno at the end of a show as he was leaving the stage. My first real Brush with Greatness. 

I had weeks to prepare a five minute set. Which seemed like forever to be in front of a room full of strangers with nothing between me and abject humiliation but putting words together they would be entertained by. But in reality, it's not that much time for more than a half dozen ideas strung together. I had a few impressions I wanted to do. Stuff that was contemporary then but are ancient now. George W. Bush. Pee Wee Herman. A few jokes about sitcom or commercials of the early '90s. Probably really hacky stuff but relevant for a guy with not much life experience but a lot of time in front of the TV.

To say I was scared as the time approached is a gross understatement. Like saying Hooper was somewhat perturbed when Ben Gardner's head popped out of the boat. Friends were counting down the days. People were telling me they were coming and who they were bringing. The pressure was insane, and entirely self-imposed. I had no plan for the rest of my life if I went up there and ate it as bad as half the other Open Mic'ers I had seen. 

At Nick's, it felt like everyone I'd ever met was there and brought their families. The host was a working comic, very funny and nice to me. But he explained with so many people were there to see me that he had to put me on last, so the room wouldn't clear out. And, I assumed, to make money since, when Weymouth shows up anywhere, Weymouth drinks. 

The thing is, it was a two hour show. What I didn't know until much later is that comedy shows, on average, run about 90 minutes. There's just something odd and magical about that 91st minute where people just get tired of laughing and want to go home. I'm glad I didn't know that because the show started at 9 p.m. and he was bringing me up at 10:55. Waiting those 115 minutes was by far the hardest part. And it didn't help much at all when my brother Jim said in front of his whole table, "I just want you to know that if you bomb, for the rest of your live I'm gonna call you 'Nick' so you never forget it." Thanks, bro.

I'm being completely honest when I say the time I finally stopped freaking out was when I got introduced and took the microphone. As God is my witness, it was the most relaxed I'd felt in days. Just a weird sense of calm like I belonged there. I mean, I was still focused and wanted to get all the stuff I'd worked on to come out of my mouth right. But I was pretty confident I had this. Especially early on when I realized there was a table of women off to the side that I didn't know and I was getting laughs out of them. Afterwards the host pulled me aside to say that one out of ever 10 Open Mic'ers have a chance to make it, and I was that one so to keep coming back. He corrected a couple of jokes I'd done, pointed out one or two that had been done before and to avoid those. But it was all constructive and encouraging and, after drinking my face off, I knew I wanted to keep doing this. 

So that's how it started. One of the things in my life that I am most grateful to Younger Jerry for taking a chance on himself. It's given me thirty years worth of some of the best experiences of my life. Right up there with coming to Barstool and asking out my hilarious Irish Rose. As a matter of fact, we met about a month later. She lived in Cambridge and I had already booked an Open Mic slot at the old Catch a Rising Star in Harvard Square and invited her to come. The host of that show was a local guy by the name of David Cross, who was still a year or so away from a complete domination of comedy television. He was actually kind of a dick to me, but not in any way that did lasting damage. More like snark, and I can definitely see where he was coming from. But the payoff was worth it because after I was done, some guy a few tables over who wasn't really feeling Cross' standup yelled "Put Jerry back on! At least he was funny," while my future wife made hearteyes. I've never owed a complete stranger more in my life.

Since then I've gotten to work with a few huge names, which I appreciate. One time Steven Wright came into a place where I was hosting in order to work on material for his next HBO special. And he came through the crowd after his set to say thanks and that he really thought I was funny. (To which the Irish Rose said, "Who is that again?" And I put it like this: "Ted Williams just walked across a crowded room to tell me he likes my swing.") My sons never cared at all that I get paid to tell jokes until one of them asked me if I ever worked with Joe Rogan and I got to tell them about the times I opened for him. I also got to take a road trip up to Maine where I picked up the late, great Patrice O'Neal in Boston and drove him home after. This was before he really blew up but when everyone already knew he was going to. And the fact I successfully followed him without bursting into the flames from the comedic fire he lit in that room is one of my proudest achievements. So is winning the 1991 WBCN/Stitches Comedy Riot. The next year the same competition was won by a sketch group that included Dane Cook and Bobby Kelly. It took a gang of them to walk in my mighty footsteps. 

And of course I recognize every one of those names are giants who've made billions in comedy and I haven't. I regret nothing. Early on I decided this is a great side hustle but I never had the desire to make it my life. I took one week long road trip once and knew life on the road was not for me. "Good Will Hunting" was still relatively fresh and I remember telling myself I'd rather see about a girl. And be home with her after the shows, not alone in some hotel. And not spending every day with 1.21 jigowatts running through my nerves because I've got a show that night. I just wanted it to be fun. To make friends in the business and work with people I like and entertain rooms full of strangers, without all the pressure.

Mission accomplished. At some point, it became much easier. When I got older and had more life experiences I could turn into natural, organic comedy that general audiences can relate to, I got more confident and started enjoying the hell out of these shows. My comic friends and I have said hundreds of times there is no better show to do than a hall filled with suburban sports parents there to raise money for some cause like a sports league, have a few drinks around a plastic table cloth with bowls of Goldfish and Doritos and forget the cares of the world. 

Not that you don't get amped up to do a good job for them. Just that you know it'll be good and it becomes a self-fulfilling prophecy, from the minute you take the mic. To call it magical would be stupid showbusiness B.S. But it's sort of …  chemical? I guess? Just a relationship between you and the room that is hard to describe but it's a blessing to be on the spotlight side of it because it's among  the best feelings I've every experienced. 

Even if it doesn't go according to plan. One I had a buddy at a show and he said, "You know what my favorite part was? When that joke fell flat and you told everyone, 'i's OK. The last audience liked one but we'll get through this. It's a buffett of jokes and you can pick what you want.' Instead of getting all nervous and making it awkward for everybody" Which was improvised. And just came out of not sweating every show like my future depended on it. Another time my brother was in from Alaska, seeing me perform for the first time. Something about the pressure of that almost broke me. For real, I got inside my own head about six minutes in and felt like I was having a panic attack. But rather than stop, I slowed down and got through 25 minutes. And when I was done my friend who was sitting in the back pointed out all the tables that gave a Standing O. I had no idea. But lesson learned about taking it easy.

Actually one of the best life lessons I've ever had came from another comic who was great about taking me under his wing, more or less. And it's something I've tried to apply to everything I do. And to hold others to it. He said that working at comedy is a pie chart. But that every piece of the pie is the same size. Yes, you need to be funny. But it's just as important to show up early. To your time (meaning don't do 15 minutes if you're told to do 10). Be easy to work with. (Which to me is especially important. If you're going to be some difficult, demanding, pain in the ass diva like Marlon Brando refusing to come out of his trailer, you better be the actor Brando was.) That's the standard by which I judge all other people I interact with. Comics especially. And it's served me well.

So I guess that's my story. I hope comedy clubs come back soon, because it's been too long and after a while you need to chase that high. It's one you don't get from really any other thing. Even though I think just about every comic has a love/hate relationship with it. I think it was Dana Carvey (don't hold me to that) I heard once say that he secretly hopes that every show he does gets canceled at the last minute. Until he gets on stage. And then he remembers why he does it. It was like he was in my brain because I've been thinking that my whole career. 

But if you've read this far and you're considering trying stand up, my advice is do it. Don't let your short time on this spinny blue billiard ball go by without taking that leap. I can't imagine what mine would be like if 1990 Jerry didn't nut up and try that dangerous, risky thing that has been one of his favorite life choices for the past 30 years.