Road Comedy Recap: The Pitts-burgh and ChicaGOAT epic

This week I hit the road again for a Thursday gig in Pittsburgh (at this point, based on my three shows in Pittsburgh since 2021, my next audience may actually contain a negative number of people) and a Friday/Saturday in Chicago, with the Friday show being a live Making Podcasts Great Again and Saturday being a headlining stand-up set.  Following our great live show in NYC for MPGA and wanting to keep working out my new hour, this was a week I was looking forward to for a while.  Unfortunately, I have not been this disappointed in Pittsburgh since I heard racial slurs yelled at a Steeler game in 2009. However, I have not been this happy with Chicago since Karl Malone won game 5 of the 1998 Finals with 39 & 19 to send the series back to Utah (in Game 6 Michael Jordan shoved Bryon Russell).  So let’s get into it, as I sit in a downtown Chicago Starbucks waiting for my 6:40pm train back east.

Days 1 & 2: Pittsburgh

The toughest part of any road trip is leaving and having my dog Cookie give me a sad look (she now understands that suitcases mean the big man is going to deeply betray her for 2-5 days).  I made my way to Newark Penn Station and hopped on the Pennsylvanian which runs from NYC to Pittsburgh. It is a cozy 9 hour ride, during which I read the newspaper, the New Yorker, The Atlantic, a little bit of a book and watched a couple of episodes of a Paramount+ show (FYI – Paramount+ is the single worst streaming app and it is not close, in terms of app crashes/failures/etc).

I arrived in Pittsburgh and went and checked into the nearby Hampton Inn.  The woman checking me in was extremely hot, but something about a folksy Pittsburgh accent makes even the hottest woman both approachable and reprehensible.  I mean it isn’t a Philly/Baltimore level accent atrocity, but it is a real boner killer, which does help when you have to walk away to the elevator to go to your room.  I then walked briskly to the Capital Grille before the closed, because I eat for the ticket sales I want, not the ticket sales I have.

I got a decent night’s sleep and then in the morning, after a 2 Belgian waffle breakfast (I have told people that I was made to be in the Midwest – *Ric Flair cadence* I’m a Church-attending, flannel wearing, cheesecake factory eating, fat son of a gun and I’m having a hard time keeping this cholesterol down… WOOOOOO!”) I checked out of the hotel. Now I took a long, thorough shower late that morning because I would have to appear on TV in Chicago before I might be able to shower again. I will explain later…

The show was at Club Cafe, which is a perfect place for someone possessing my apathetic fan base.  It is small enough that 50 people would feel like a crazy party, 40 would feel like a sold out club and 30 would give a feeling of pride.  How many people did I draw? 16, which is a number that gives “Joker origin story, pre-musical.”  The fans that did show up there were great and I am appreciative of their time, money and support and I think I gave them a strong show (it was always meant as a tune up for Chicago), but all I kept thinking toward the end of my set was “the stage is a little hotter than I expected – I hope this sweat doesn’t create a funk that lingers for TV tomorrow.

I said hi to the fans after the show (my third straight show where my opener’s fixed pay was higher than my ticket sales-dependent pay. This is known in the industry as “fucked.”  I then got on the midnight train to Chicago (the Capital Limited featuring the train attendant Carlos, a railroad joy well known to my Patreon subscribers).

Day 3: Trump Arrives in Chicago

When I woke up we were in Indiana, home of gay political icon Mike Pence. And also Pete Buttigieg.  We arrived in Chicago on time and I had a few hours to kill before Windy City Weekend. Now for the promised explanation:

Since the pandemic, Ryan Chiaverini, a TV host in Chicago (think if Ryan Reynolds were the Mario Lopez of Chicago), has been a big fan of my work, but unlike my other fans and my friends, he actually backed up that verbal support with action!  When I told him about my show, he told me he would be unable to make it, but could book me for a segment on Windy City Weekend.  I said yes, of course, and then the producer told me that I would need to arrive TV ready. Well, I was sleeping on an Amtrak on my way into Chicago overnight, so I guessed I would be TV ready, if the show were “Real Homeless Housewives of Chicago.”  Now I have been told that there are shower facilities in the Amtrak first class area of Chicago Union Station and I will leave the mystery of how I cleaned up for TV as a cliffhanger until I post video clips of my set in Chicago.

I arrived at Windy City Weekend 10 minutes early and met Ryan’s co-host, the lovely Val, then Ryan and then Ryan’s friend who I had done a cameo for a year or two ago (seriously folks – I am the cameo GOAT).  My segment went great (watch HERE) and then I met film critic Richard Roeper who was there for his usual segment and we shook hands, Twitter follower a Twitter follower.  I then made my way to Oak Park, IL to check into my hotel.

I killed some time, got some BBQ with my MPGA co-host, Jay and then we went over to the club. The club is new (and the town feels very new or refurbished) and really nice.  The show went great and it will be up on podcast platforms this week.  Without giving anything away, I believe the loudest laugh in show history may have been to Trump’s answer of “Narcan” to a question that was asked.  I then went to have a beer with some fans (the trio of gentlemen Andrew, Aaron and Kevin (gents – please correct me on names if I am wrong) who I met after my St Paul shows and they said they would be at an Oak Park show. They showed up 10 or so deep!  Promises Made – Promises Kept!) before retiring to my hotel room to watch Bill Maher complain for an hour.

Day 4: ChicaGOAT

When you have God and Trauma-given talent you can always be assured of delivering a good performance.  But you aren’t always guaranteed to set a suburb of Chicago ablaze. Well, Saturday night, Oak Park, Illinois was blessed to have me at my best.  The new hour of material killed (and I finally did the huge chunk on the NHL that I have been dying to do and it crushed) and the fans were great (i.e. no one had tips for me on how to improve jokes, but they did have money to buy merch!).

Opening both nights in Chicago was my friend, comedian Nick Cobb, who I probably have not seen in somewhere between 5 and 10 years, so that was a nice added bonus to working Comedy Plex.  Sadly, weekends like this are rarer than I would prefer (meaning I am not getting the bookings I desire), but they are so great when they happen that it keeps me going on my quixotic journey for sustained comedy success.

I felt especially generous complimenting the Chicago crowd on being home to the second best basketball player of all time #KingJames

Day 5: Mass and the Midwest

After a rise n grind meal of bagel, chocolate long john (the more homoerotic, the better the Dunkin Donut – hence why my favorite is one I have only found in Boston – the “chocolate glazed stick”) and coffee from Dunkin Donuts before walking to St Edmund’s for 9:15 Mass.

I will say this about the people of Chicago. More immature J-L would often comment that downtown Chicago just felt like a land of 5’7″-5’8″ 8s (in other words, if there were a draft of men for cities, like they were sports teams, Chicago would have me high on their draft board as someone who would fit in perfectly to their system of Midwestern values and breeding nice looking power forwards and left tackles).  Now while this remains more mature J-L’s assessment of the women of Chicago, he also noticed that people just seem friendlier here than in New York and New Jersey (not a big surprise I am sure, but it is deeper than just a cliche). Strangers of all races and genders said hello (to be fair this was also the case in St Pete’s Beach, FL). A woman broke off from her husband to ask me how I liked the book I was reading and told me the author has a new one out.  And the husband did not even ask to watch while we made love! Midwest values!

That said, it was not all perfect. When I went to see Smile 2 on Saturday afternoon, the theater machines would not let me order a milkshake, so I had to settle for a popcorn and water – disgraceful.  And the man sitting next to me in the theater was eating his wings  in a manner that led me to believe he was told it is rude to close your mouth while you chew.  And he went “mmm mmm mmm” every time something suspenseful happened, which in a two hour horror movie is pretty much all the time.  He would have been the worst, but for the woman who had her baby at the hard R-violent horror movie. Naturally, the baby cried at multiple spots until she finally stepped out of the theater (its almost like a baby instinctively recognizes that a woman having her eyeball cut out with glass is a “bad boo boo”).

But all in all, I had a great time on this trip and gave three good performances for 2.2 audiences (yes Pittsburgh – you are the 0.2).  I guess come see me in Emporia, Virginia or Princeton, New Jersey if you want to experience the same!