The first comedy club I ever attended was the DC Improv on a trip with my brother. The first comedy club to ever pay me was the DC Improv for a week of emceeing.  So 18 years into my comedy career, which started at a jazz club open mic in Washington, D.C., it would not be an exaggeration to say that I achieved a real and personal milestone by headlining a weekend at the DC Improv.  It was a great weekend during which I connected with fans and old friends. had a genuine DC power lunch and had a few new bits achieve near-instant legend status.  I also sat next to a weeping pre-teen at the new Spider Man and experienced a momentary, but deep crisis of faith in my comedy career (duh). In other words, a uniquely typical road comedy experience for me, so without further adieu let’s get into it!

Thursday

After working from 7am at the day job I made my way to Newark Penn Station to catch the 315pm Accela to DC (with first class coupon upgrade).  It was an uneventful, but as I joked on stage all weekend – why is the first class car the first car on the train?  If a tragedy were to occur, shouldn’t the successful people in first class have a 4-5 car buffer of less worthy people in front of them? We should not be the tip of the spear in an accident!

Got to DC and made my way to the Farragut North station, which sounds like a drunk Dave Chappelle telling people where Dupont Circle is, to go to the AC Hotel, where the club was putting me up. I loved the hotel, though it did have a weird shower and a square toilet (I will never understand hotels that in the name of style and ambiance tinker with basic things that have been perfected).  I then had about 10 minutes to relax before heading out to the club for the first show of the week.

The show went really well, the crowd was great and to celebrate I went and did 90 more minutes of legal work in my hotel room to meet some billing requirements.

Friday

On Friday I had to wake up early to (drumroll please) do day job work because I was having my first real DC power lunch with David Frum. He had been at the Thursday show with his family and though the show went really well, my sole concern, knowing we would be having lunch the next day, was if the show would go well for DF. He did enjoy it so I knew our lunch would not be a 2 hour conversation dancing around the previous night’s comedic failure.  We had a tasty lunch (I had Rigatoni Bolognese) at Et Voila and discussed comedy, politics and more.

After lunch, as I waited outside for my Lyft, a man started approaching me with a look of recognition. As he got close I realized it was a man named Mark and he had been a year below me at Williams College.  I processed quickly like the Terminator and he said “do you remember me?” and I was like “Mark from Williams!”  His wife followed once it was clear that we were both the people we thought we were from 20 years ago. They told me they had been big fans of my stuff during the pandemic and then it came up that he was an assistant GM for the Nationals.  This is a more than common occurrence when interacting with Williams alums. I have a cool YouTube page… you have a World Series ring!

After the Frum power lunch and the Washington Nationals power chat I powered my way back to doing more powerful day job work at the hotel.  Then it was time to crush 2 Friday shows.  But when a comedian makes plans to crush, God laughs.  But not in a good way.

Frist show was actually really good.  It was a full crowd, thanks in no small part to the quasi army of my girlfriend’s friends and family that came through. An older, unpublished bit I dusted off on gummi vitamins tore the roof off (as it would for every subsequent show as it continued to rapidly get better as I began adding more tags in real time).  The star bit of the weekend, however, was definitely my multi part story about Georgetown Law professor Neal Katyal (who wrote a reference letter for me in law school) outpacing my entertainment career.  It is so good that it, along with gummi vitamins, may have extended the lease on my comedy career.

One bit that did not go over as well I hoped (it was the most inconsistent bit of the weekend, but when it hit it did hit big) was basically me offering vulgar and emotional sympathy for Adele’s ex.  During the Friday early show it was the only bit that earned any heckles… and they were from my girlfriend’s family. Here is a pic of me and my girlfriend after the show when I found out:

After the show I took Alex, a devoted member of the Making Podcasts Great Again fan community, and his wife out for a promised drink. Alex came to NYC solo for the taping of Half Blackface so I thought it was the least I could do.  In the course of just a half hour before the 2nd show I learned that Alex was infinitely more successful and accomplished than me.  I won’t discuss his career since it is not my place to do so, but I think my own insecurity about my comedy career made me presume/project a lack of success on to my fans (“well, they love my comedy so they must be at the end of the line!” – to be fair, since it did take an apocalyptic event for my career to finally take off, that is a more rational response than it would be for a comedian who did not require a Biblical plague level event to gain success).  But mostly it was just nice to be able to show a little appreciated to a fan. And then I asked him if I could borrow money.

The second show would be the one that would leave me sad.  The crowd was not big, but that was not the problem.  I felt like I was having a very good set, but instead of a full house where the energy feeds off of itself it was small enough that big laughs were borderline impossible, both because it was 1/3 full and because when crowds are small they seem uncomfortable laughing loudly because there is a much bigger chance of shifting the focus onto yourself.  So during the course of the set I made about 6 allusions to suicide (all jokes), but otherwise gave a strong effort.  When I left the stage I didn’t feel great. I felt like by not being able to pack every show I had put fans in an awkward position.  That feeling was only augmented by the kind words from the fans who were there.  They did enjoy the set and one quartet said they came down from Baltimore that night specifically for me on their friend’s birthday.  Instead of making me feel good, it actually made me feel bad.  If you come to see me from another city I feel like I owe you a great experience and it is almost impossible to have a great comedy show at 1/3 capacity.  Not that it can’t be good, but when there is too much silence or too low energy that responsibility falls to the headliner for not getting more people.

When I got to the hotel at 1 am I woke up the girlfriend to tell her that I think I needed to quit comedy.  It is one thing to fail myself, but I felt like I had failed fans, even though they said they loved the show. My girlfriend’s response, reflecting both her fatigue and familiarity with this subject was “uhhhh zzzzzzzzzz.”

Saturday

When I woke up Saturday I still felt a little bummed, but the feeling started to subside as I realized I really had had two strong performances the night before.  I went for a long walk through DC with the gf before she had to leave for home.  I then went and saw Spider Man: No End in Sight, or whatever it is called. I know it is setting records and people love it, but I am kind of done seeing Marvel stuff in theaters.  I think Disney+ is the right venue for me from now. I actually really liked the first Tom Holland Spider Man movie, but the new one and the one preceding it I thought were just fine. Considering the entire Spider Man film universe spans only 20 years, it seems now that anything 5 years or older counts as nostalgia for the Marvel fan base that is America.  I don’t think the movie was bad, but hammering me with memories of the last decade of movies seems to be enough for people to categorize something as “great.”

To make matters worse, the very chatty 11 year old next to me in the theater began weeping halfway through the film during an “emotional” part.  When I was his age I cried at Dead Poets’ Society and Glory, not Teenage Mutant Ninja Turtles.

Saturday’s shows were absolutely great.  Both were sold out and I would like to say good things about the early show, but the problem is I am so proud of what I pulled off on the late show.  As I watched the emcee and feature on the late show I could see that the crowd was very chatty and quite possibly very drunk. There was one woman in the back that I referred to as Max Cady (think 1991 Cape Fear movie theater scene) because her laugh appeared designed to only distract and not register enjoyment of comedy.  I told Jon, the emcee, “well I won’t be going over my time with this crowd.”  And then I had my best set of the week. Every bit worked and I don’t know if I presented an intimidation or an “I don’t care” attitude on stage based on my low expectations for them, but whatever algorithm I unlocked, it was the key to the crowd.  When I finally got to sleep that night I felt like I had redeemed myself and was especially happy at referring to the Spider Man weeper as a “future adult gummi vitamin consumer if I’ve ever seen one.”

Sunday

I woke up Sunday and went right to 9 am Mass at the Cathedral of St Matthew, like I always do when in town (very beautiful Church). Then I had some time to kill at Panera Bread before heading to a noon show of West Side Story.  A mask-less, mustachioed man saw me pouring a cup of “medium roast” coffee and looked at me and said “Medium Roast guy, huh?”  And I wondered, “is that MAGA for “you suck di*k huh?” or closeted code for “you suck di*k, huh?”  Just happy he didn’t see my digital ticket to West Side Story.

The movie was solid (reviews of both will be on this week’s Righteous Pk Podcast and for patreon members of Making Podcasts Great Again, Trump will review Spider Man and Mike Pence will review West Side Story) and afterwards I went for a walk with my friend/law school classmate/guy who taught me that people with southern accents could still be extremely smart, Hank. Hank (and his brother) were actually the first two people at my first open mic in DC. So when he emailed me to let me know that he would be in town visiting his siblings the same weekend I was performing I thought it was good fortune that he would be there to see my final show (kidding).

But then a flood of messages started pouring in. Fans and Hank messaged me that they would not be able to come due to Covid exposure and/or Covid fear. Totally understandable, but still deflating when expecting a lighter crowd on Sunday evening.  As I said on stage, “I hope (those missing) only get long Covid, nothing worse. AM I NOT MERCIFUL?” (I know it’s 21 years old, but Gladiator still seems to be a movie I quote a lot regarding my comedy career).

As soon as my set was done I grabbed my check, my suitcase and made for the train. Got on my Amtrak with plenty of time and watched Mr. Smith Goes to Washington because I am a rebel and felt like watching it as I left DC was a real middle finger to convention.  I then began crafting this blog, which is being finished now, in my kitchen, before a long day of legal work.

Thank you to everyone who came out to the shows. Hopefully you all enjoyed it. And if you are reading this and are not in the DMV area, get your tickets to see me in Chicago, San Jose, LA and Utah (please).  And here is a picture of Cookie this weekend, looking very unsure without me in the house.