• Steve

10 Years From Letterman


Today is 10th anniversary of my stand-up comedy set on “The Late Show with David Letterman”


In honor of it I’d like to share the memories I have of the day/week I taped it. This is just about the actual day/week I did the show.


Friends & fans know the entire long road to that week and show was a roller coaster of it’s own. That story has been told many times by me in talks, books, articles etc… AND I believe, told best by the fantastic film-makers of “Dying to do Letterman” (Available HERE FREE on Amazon Prime! #shamelessplug).


Please check the documentary out if you haven’t. It’s an incredible ride. But in honor of the airing anniversary I’d like to just concentrate on the week I taped itself. That day has a story of it’s own you only see a small part of in the movie. So I’d like to share what I remember of it, this decade later.


The booker of “The Late Show with David Letterman” Eddie Brill, called me on a Wednesday in late August 2009. I was returning a rental car with some other comedians. I looked at the phone and saw Eddie’s name. It got me excited and frustrated at the same time. I had been sending Eddie DVD’s and links to my comedy for almost five years at this point. Some times he called me to tell me why what I sent him wouldn’t work on the show. Other times he didn’t respond at all (I knew what that meant). Eddie was always encouraging when I spoke with him. Even though he was always telling me the jokes weren’t “good enough” or “right” for the show. But even though he handled it the nicest he could I was still left depressed after each call. It always felt like I was getting further away from being on the show, not closer.


Again this is a reflection on me not Eddie the booker. I can’t imagine having his job. He made hundreds of comedians dreams come true…but he also had to break the bad news to many more thousands. Tough thing to do. He handled it better than I would have.

Anyway when I saw his name I felt excited… and then almost immediately beaten. I knew this was gonna be another call of him telling me why what I had sent him wasn’t gonna work. I even showed the other comics his name on the phone and rolled my eyes. They all got excited. “Answer it, you idiot!” They hadn’t gone through four plus years of rejection calls from the show. They hadn’t sent bit after bit to him being sure “this was the one”… only to be told it wasn’t. I knew I would never quit chasing my dream to be on the show, but I wasn’t handling it as well as I had before.


I stepped outside the rental car office and took the call. Eddie sounded extra pleasant. He pretty quickly told me he was going to put me “on TV.” I started to let myself get excited. Then I let doubt creep in and asked if it was on Letterman OR a different TV show. Eddie laughed and said of course it was on the Letterman show!


NOW I let the excitement take over. I can feel the excitement again as I type this. My mind whirling. My hands shaking. My stomach full of pterodactyls. I broke into a smile I couldn’t speak through. I turned to look at the rental car building I was standing in front of… the other comedians were all lined up inside at the giant window watching me with anticipation. I smiled bigger and tried to give them a “cool” thumbs up—like this somehow happened all the time. They all knew that meant “YES!” They started pounding the window and jumping up and down. I still love all of them for showing the excitement I was feeling (but holding in) in that moment.


The booker told me I was going to tape the show the following Tuesday. They wanted me there a day early in case travel got messed up. Less than a week from then I was going to be on. In those 5 days I had to fly home to Los Angeles from the East Coast, get a suit, practice the hell out of that set and fly to NYC. I remember thinking I didn’t have enough time to run the set in front of audiences as many times as I wanted. Eddie, the booker, told me a bunch more things and details but I don’t think I heard any of them. I told him that. He said he understood and that someone from the show would be contacting me to arrange it all.

When I hung up all the comics ran out and hugged me. We hi-fived repeatedly. Even hours after that. It was great to share it with them. Comedy is usually a lonely business. Onstage alone. Traveling alone. In hotel alone. I got to experience the moment with a bunch of people who understood every bit of that.


I called my wife, Denise, and shared the news. I think she cried. She knew this whole journey from a non-comic’s perspective. From a partner’s view. It’s strange I’ll never know all the feelings she had that day. That week. I know she was happy and excited and proud. I felt loved and that WE had reached something together.


That evening I flew home and stared out the window of the plane the entire 5 hours. The clouds that day were amazing. So gigantic and fluffy and brightly colored. The kind you’d imagine landing on, not falling through. It was the perfect view for what I was feeling inside. I felt like I was hovering magically above the Earth. I mean I was in a plane, but it would have felt like that anyway. You know what I mean.


I got home and shared the news with the rest of my friends and family. Denise had started a checklist of everything I/we needed to accomplish before flying out to NYC. I started to call every club I to get a guest set, so I could practice the routine. I remember doing the Comedy & Magic Club, The Hollywood Improv, The Icehouse and The 3rd Street Theatre. There were more but those are the ones I remember.


Funny story about the Hollywood Improv guest set. I was there to run my set for the last time before heading to NYC. I was waiting in the hallway and scheduled to go up next. It’s always awkward running a TV set in a normal club setting. You can’t really be loose and engage with the crowd. You need to be still, focused, exact. No extra words or movements. No interaction. You do it like you’ll do it on television—which is the opposite of how you’d perform in a club. So you stick out like a sore thumb onstage when you’re practicing a TV set. But you have to do it and it’s unnatural and nerve-racking. So I’m in the hallway running the set in my mind and I see Carlos Mencia walk in. NO!!!!


Any comic reading this knows what that means. For non-comics it means there’s a strong chance I won’t get to go up. Stars often pop in and do unscheduled sets at clubs. It’s routine. They’re stars so it’s great for them, the crowd and the club. But often when this happens someone who was scheduled to be on the show gets removed. Not all the time but a lot of the time. UNLESS it’s Carlos Mencia. Then everyone usually gets scratched because he never does less than a half an hour, even if he says he’s doing five minutes. So by the time he’s done there’s no time for anyone else.


I’m not making a judgement here, it’s just how it is with him. OK there’s a little judgement. Anyway I quickly see my last West Coast chance slipping away. I panic. Decide to be bold. I walk right up to him and tell him I’m doing Letterman this week and I’m going up next. He doesn’t seem to really care and asks who is running the show going on. Once he meets that guy it’s over. I’m feeling dejected. I look at my friend Biagio who is a filmmaker and is there with his camera. I think quickly and say “Biagio, it’s Carlos Mencia!” Biagio jumps right in and runs over to meet him, camera in hand. Biagio says some nice things to Carlos and engages him in compliments and industry talk for just enough time that the show runner comes out to the hallway. He asks if I’m ready. I say, “yes” and try to rush him back in the showroom. He notices Carlos. “Is that Mencia?” He asks? DAMNIT! “Uh yeah…but he’s talking to some filmmaker. Better wait to talk to him when he’s done.” The booker nods in agreement and we go inside. YES! I run the set. It goes OK. Carlos goes on after me. Everyone else gets scratched. My quick thinking and Biagio’s improv skills got me a set that almost slipped away. What I’m saying is I was on a good run that week.


My wife Denise wasn’t able to make the trip to NYC with me. Again if you want more of that story see “Dying to do Letterman” on Amazon Prime for free. Shameless plug 2. I flew out to NYC on Monday by myself. I was feeling a little lonely even though the biggest day of my life was coming. My dream was coming true but because of the quick notice of it all a lot of friends and family who shared the journey could not be there. Lots of friends who said they’d be there when it happened couldn’t. So I arrived at JFK alone. I went into the city alone. I arrived at the hotel alone. The hotel was a couple blocks from the Ed Sullivan Theater. It was called The Dream Hotel. Seriously. That made me feel a bit better.


Eddie Brill picked me up at the hotel Monday night and we went to a couple clubs in NYC to practice the set. I wanted the practice but I’d also heard awful stories of comics not doing well on the practice sets and then not doing the show. That never left my mind. I ran the set three times that night. After the second run-through Eddie suggested removing the first 25 seconds of the joke. He thought it would work just the same without it. I resisted. I wrote the joke this way. I honed it this way. He approved it this way! But Eddie thought it would work just as well without it and we’d get into the heart of the bit quicker. I honestly didn’t even want to consider that he might be right. My point was it was the night before I was going to do it on TV. I’d done the joke hundreds of times one way—18hrs before doing it on TV was not the time to mess with it.


Eddie pushed harder and also suggested a tagline for one part later in the joke. I felt pressured and had the idea of losing the TV spot in my mind. He convinced me to try it his way on the final practice set that night. I relented. The joke worked fine with the changes. But that was only one time I’d tried it that way. One time doesn’t tell you a lot about a joke working or not. I was still hesitant to do it this new way.


Eddie insisted and I felt II was in no position to say, “No I wanna do it the way I’m used to.” He was giving me this opportunity and so I had to compromise. I said I’d cut the first part but I didn’t want to do the extra line he suggested later. He agreed.


IF you’ve ever seen the documentary “Comedian” with Jerry Seinfeld you might remember a scene where Orny Adams goes on Letterman. They ask him to change one word in a joke he’s doing on the show. Hours before the show. They want him to change the word “Lupus” to “Psoriasis.” We can all agree Lupus is a way funnier word. Orny rightly stresses out about the change. He didn’t write it and hone it that way. Who knows if that will work? I had seen that documentary and now it was all I could think about. He had to change one word in the middle of the act. I was removing the first 25 seconds of my joke. The introduction. The jumping off point. The launching pad!


Plus I was already doing something a bit different. I was doing a set that was entirely one bit. One topic. No changes in subject. It was one long story about one thing. If it wasn’t working there was nowhere else to go. Usually comics on TV have four or five different jokes or topics they hit. If you’re not liking something don’t worry cuz there’s a change-a coming! It’s a little freer. Easier to be confident in. I had only seen Jake Johannsen and Brian Regan do one long bit on Letterman. They were comedy Gods. They had done the show 30+times each. This was my first time. I was attempting something difficult already. A tightrope with no way off. And now it was changed the night before. With one run through. I was scared. But what was the alternative?


My mother was the only family member able to make the trip to New York on such short notice. I met her back at the hotel and we decided to go out and grab some late dinner in the city that never sleeps. We walked to the Carnegie Deli a few blocks away. I told her about the change to the joke. She was concerned but told me things would be alright. She did it in that way that mothers do where it helps even if you don’t believe them.


The Carnegie Deli was packed even though it was after midnight. It’s closed now, but it was the kind of place you sat at tables with strangers. Even though I had to fit in a new suit the next day I ordered some comfort food. My mom got a slice of cheesecake the size of the ribs they put on the Flintstone’s car. After a few minutes it started to thin out and I noticed Howie Mandel sitting across the restaurant. I had done some audience warm-up on “Deal or No Deal” when it started but knew Howie would not recognize me. However, my mom wanted to meet him. So when he got up to leave I said his name low enough so only he would hear it and he came over. I asked him what he was doing in New York and he said he had been on Letterman that day. My mother seized the moment and proudly proclaimed “My son is doing it tomorrow!”


Howie laughed and smiled at her pride, then looked at me. I told him I was a comic, but didn’t mention “Deal or No Deal.” He wished me luck. My mother reached out to shake Howie’s hand. Now I laughed because it’s very well known Howie is a germ freak. So he made a fist to “bump” my mom. My mother just stared at it, as any normal person would. I said, “Howie doesn’t shake hands, Mom. He fist bumps.” She gave me a look like she understood but I could tell she did not. My mom then reached out and enclosed Howie’s fist in her own hand and shook it like you would in a handshake. Fist in hand. Howie was taken aback but you could tell appreciated the humor of it. He quickly said goodbye and good luck and left. I’m sure to find the nearest bottle of Purell. The hilariously awkward moment got me out of my head and allowed me to let go of the joke worries for the night.


I tried to sleep in, but that’s pretty hard on the biggest day of your life. My best buddy Gary was the only friend able to make the trip to NYC on short notice. We met up in the middle of the day to grab lunch. We walked around for an hour trying to find just the right thing to eat—nothing too filling, but something to soothe my stomach. We decided a salad would probably be the best thing. Gary nor I are regular salad guys. But we knew that this was the moment for it, and that a better meal would come after the show taping. Strangely, it was hard to find a place to just grab a decent salad in the greater Times Square/Broadway area. Lots of great delis, fine restaurants, chains, and of course pizza places. But not a place to grab a quick salad. We looked for an hour before realizing it was going to get too close showtime to eat. So this is how, on that very special day, we came to eat at an Olive Garden. Yes, Olive Garden. We were in the greatest culinary city in the world and we went to Olive Garden. NYC home of the greatest Italian restaurants outside of Italy—and we went to Olive Garden. We knew it was wrong but we did it. I had a great salad and my stomach was good fo the day.


After lunch I went back to the hotel and ran the set into the mirror a few dozen times. It felt weird the new way, but each run through was a little less clunky. I took a shower and as I was getting dressed I realized I hadn’t packed enough underwear. I needed to go shopping. I couldn’t wear old dirty underwear under my new Hugo Boss suit!


Truth be told Gary wasn’t the ONLY friend to make it to NYC. My Friends Joke & Biagio made it too, But they were also there as the filmmakers that were capturing the whole journey. They checked in with me after lunch, and when I told Joke I had to go buy underwear she said they needed to capture this ridiculous errand for the movie. Now a decade later I don’t remember them bringing cameras on the shopping trip, but I do remember them helping me find a nearby store, walking there with me and choosing the perfect pair.


At that time Letterman was taping two shows on Tuesdays. An early one that aired later that evening, and a late one that aired on Fridays. I was on the second taping. Eddie Brill told me he would call me after the first taping and let me know when to come. Waiting for that call was nerve racking. I heard endless stories of comedians being “bumped” or scratched from the show because other parts of the show ran long, or for unforeseen circumstances. Ray Romano was bumped twice before he ever got perform on the show. With an early show it felt to me like there was more of a chance for this to happen. If someone famous was on the first show and got bumped, why not just slide them to the second show since they were there?


I was back at the hotel rehearsing when Eddie called. Just like his call at the rental office 6 days earlier I picked it up excited and scared. Eddie was in a great mood. He said the first show went great and to come on over. It was a GO! I packed up my suit and walked the few blocks to the the