The Downside of Booking Yourself

What a crazy clusterfuck this past week was on the road. 22-hours of driving over the course of 3-days, and why? Because I’m an idiot.

It started back in April when my buddy told me about an awesome room in Midland, MI that is actually in a theater. I emailed the booker and found out that this room was available on a Thursday in early October. I decided to take it as the thought of doing a show in a theater excited me. I either didn’t pay attention, or didn’t seem to mind the fact that it was 5.5 hours each way and that I wouldn’t have a hotel provided for me that night. Much like I usually do, I thought “October is far away, I’ll figure it out later”.

Cut to July, I was supposed to work a weekend in St. Paul, MN at the end of the month. However, shortly before the week came about, I received an e-mail that due to some private party, the weekend of shows I was supposed to do had been reduced to a Friday night only show. I was given the option to still do the Friday, or reschedule when I could get a full weekend there. Naturally, I chose the latter. Turns out, the first weekend that got offered to me was October 4th and 5th. I did a brief check of my schedule and saw that I was only booked on Thursday the 3rd that week. “Perfect”, I thought to myself, now I have shows Thursday, Friday, and Saturday that weekend. In my head that helps me out more than having one show this week and two the following week. I have two kids and it’s easier for me to group the events together versus constantly having something that’s taking me out of town every week. Now, I knew I was in MI that Thursday and had to get to MN by Friday, but I thought, “October is a long ways away, I’ll figure it out later”.


Cut to later…Early last week I started prepping for my shows over the weekend and finally did the math on them. I was going to have to drive up from the Chicago area to damn near Detroit, do my show, get back in the car and drive home. This would allow me to spend a few hours on Friday with my kids. Then, I had to get back in the car and drive 6-hours to St. Paul, MN where I had to be there at 7:15pm that Friday night.

When I was in my 20’s, I could drive this whole country front and back without the need to sleep and without the need for any time of upper in the car. Your 20’s are a beautiful time of life. Body parts work how they’re supposed to and you’re too ignorant to overthink anything. Now, I’m 37-years old and I am dog-dick tired.


I did my show Thursday night at the theater with a very funny comedian from Chicago, Jimmy Roberson. The show went great and it felt like “the big time", even if only for an hour. After the show, I had to run back to the green room to grab my merchandise and ended up getting stuck behind the parade of people leaving the theater talking about how funny the show was, only I wasn’t able to get a head of them to start slinging my shit. Instead, I ended up carrying my bag full of albums back to my car in prep for the long-ride home. My goal was to make it at least half-way home before I had to stop for anything. I don’t think I lasted an hour before I stopped to grab a cup of coffee. Now, I am not a coffee drinker, it has always tasted like a bowl of columbian piss to me. But after an hour of driving dead tired, I was jonesing for caffeine like it was Krispy Kreme scented heroin. I stopped off at some sketchy gas station and grabbed a 16oz high-caffeine level coffee, because I’m a moron. I drank this thing at midnight, thinking I’d be able to sleep when I got home. For the remainder of the drive I listened to Chris Rock’s Netflix Special “Tamborine” and Dave Chapelle’s Netflix Special “Sticks & Stones”. I had already heard Chris Rock’s new special, but I got to hear it for a second time and truly appreciate the comedic genius behind it. But, then I got to Dave Chapelle’s special. This special has been causing all kinds of controversy due to some of his topics. Within the first 10-minutes of the special, I understood the controversy. He crossed the line immediately and never looked back. I personally found myself thinking that it was written brilliantly and had several moments within it that had me laughing out loud by myself. It was either the comedy or me being gakked up on coffee, but I thought it was great. I got home at 2am and got all of about 2-hours of sleep total, thanks to this new Columbian drug I experienced.

Chris Rock.jpg

Friday morning I started packing for my weekend in St. Paul, MN. I had never actually been to St. Paul before. I had been all around it in almost every other city that MN has to offer, but never St. Paul. I began my 6-hour trek there with yet another cup of coffee, because I’m a whore to what works. Getting within the city limits of Minnesota is always unique when you’re an out of town driver. Minnesota is known for the largest fucking divots these roads have ever seen. Don’t confuse them for potholes, they still have plenty of those. These are big, giant, craters that were for some reason, planned to be there on the fucking roads. No wonder they’re the land of 10,000 lakes, one good rainstorm and these fucking divots are housing fish. Minnesota also has a nice distinction of no merging room whatsoever. When a lane is entering the highway, they have all of the length of my dick to wedge their car into the right line, which is filled with 70mph cars. After that, to complete the trilogy of stupid, they have exits on the left side of the expressway, which is all but unheard of in most places. Nothing like weaving over three lanes all the way to the right in speeding traffic, only to find out that in a mile, the fucking exit you needed is on the left…assholes.

Anyway, after nearly shitting myself for the final hour of the drive, I finally got to the hotel. Well, that is to say, I parked in the parking garage across the street, lugged all my shit to the hotel, walked in to find out that it was a permanent residence, not a hotel, and decided to go back and actually check my itinerary. After checking my itinerary, I realized that I’m a moron and was at the wrong place. So I lugged all my shit back to my car and drove to the new address I plugged in. Much to my surprise, the address I plugged in was to the club itself, not the hotel. So, I had to change in my car with people constantly walking past, looking in my window, and then I got to the show an hour early. I asked them “where’s the hotel?” and wouldn’t you know, I was at the right place all along. Turns out that if you turn right in the building then it’s a permanent residence, but if you turn left, that’s where the hotel begins. Fucking Minnesota and their stupid left side exits.

The Friday show had about 25-people in a room that maybe holds 50-60. The crowd was nice, but they were hesitant to laugh out loud. Laughter is a lot like crying, it can be a very vulnerable reaction. If everybody is laughing or crying, then it’s ok to join in. But if only one or two people are laughing or crying, then you start to get hesitant and hold your emotions in. I berated the audience in a friendly way and let them know after a phony applause break that I didn’t need a pick-me-up, I wanted to earn every bit of their laughter or not get it at all. Still a coin flip to figure out how that night ended for me. Once the show was over, I sold two CD’s and hit the road back to the left side of the building to find my hotel.


Saturday came and went, and before I knew it, it was showtime yet again. I had about 6-10 people I know that live in the area coming out to the show at night, so I was excited to see them. Khadijah Cooper hosted the show and did a great job kicking it off. Jimmy Roberson went up and knocked it out of the park like he always does. I went up and did a 57-minute set and got all but one bit in from my upcoming album “Vincesectomy”. There were a few small tweaks that I made to some existing bits that I feel helped take them to the next level of funny. From there, my brother-in-law’s sister was there and wasn’t “heckling”, but was shouting stuff to me on stage. I had some fun with her in that moment, and then after the show her and her wife got me hammered. My other buddy Sean and his wife drove me back to my hotel where I got about another 4-hours of sleep before getting up at 6:30am, hungover, to drive through divots, left exits, and shitty merges to get home. In retrospect, 22-hours of driving in 3-days took its toll on me. But that’s what happens when you book yourself, you wind up piecing together any gigs you can well in advance because you’re afraid if you wait too long, you’ll have an empty spot on your calendar. But, I’ve been at this for 18-years, I can handle these drives*.

*I made it until about 6:37am before I needed to stop and get a coffee.

The Voices In My Head

This past weekend I performed 4-shows at CG's Comedy Club in Bolingbrook, IL. Each show was uniquely different and fun in its own right.

Often times people ask "how were the shows?" and the typical response is "good!". But if you're looking for something more than surface level, these were the emotions associated with the shows this weekend?

Friday 8pm Show - Crowd was about 3/4 full and I had about 10-15 people in the crowd that I knew. This causes me to overthink and go "what have they heard before, what's new that I can do, I hope I don't eat shit while they're watching, why did they come here” (cut to the end of the show). “That was a great show, I'm so glad they came, my new stuff went over really well, I should promote myself more.

Screen Shot 2019-10-08 at 10.30.15 PM.jpg

Friday 10:30pm Show - At 10:25pm we had zero tickets sold and were on the verge of canceling. This becomes the love/hate part of comedy. On one hand, you want to do the show. But, on the other hand, you're hoping that either 20 people walk in, or none do. The last thing you want is 8 people showing up right at 10:30pm and now you have a small crowd. (cut to 10:30pm). “Perfect! 8 people just walked in!” This is where the panic for a comedian starts to kick in. The size of the crowd shouldn’t matter and as a performer, you are determined to give it your best no matter what because you never know who might need a laugh that night. Even knowing that, and having done this for 18+ years, you still can’t help but think of all the worst-case scenarios of the evening. For me, the evening turned around when I heard the one lady in the crowd tell the emcee “It’s my son’s birthday and we’re here for him”. That’s all I needed to strap in and ensure we made it a great night for him. The crowd was pre-dominantly African American as was the hilarious feature comedian that night, Todd Thomas. Now, there is nothing wrong with this, but my usual “fan” is a 34-50 year old, white, male. (I’m not choosing this, this is just what Spotify analytics tell me). The combination of Todd doing so well and the demographics of the crowd had me concerned that it could be a struggle to get the audience on board with me quickly. I just had to trust myself that my experience would pay off. I got up on stage and opened with “As a fellow black comedian” (audience laughs), “we’re going to have to pretend in here tonight for this to go well “ (audience applause), and I was in! What an incredibly fun show this was. This just proves, don’t judge a book by…I’m an insecure asshole.

Screen Shot 2019-10-08 at 10.31.13 PM.jpg

Saturday 8pm Show - When I pulled up to the club on Saturday night, it was in my wife’s car, as she dropped me off. The night before I lost my car keys and had to have Glen, the owner of the club drive me home. When my wife dropped me off on Saturday, I brought my spare set of keys and found my original keys still in my car. These are keyless keys, you know, the fab that detects your proximity to the car and lets you unlock your car within range. The beauty of this type of key is that you can’t lock your keys in the car, because of the detection feature. Turns out, I’m the unlucky asshole that found a way to have his car lock with the keys inside. I still have no clue how it happened, but now I had to take shit from the rest of the staff at the club for being an idiot. I was excited to walk in the club and see my buddy Vinny Santino there. He’s a funny young comic from Florida who I met on the road a few years ago. Just a few weeks back I saw on Facebook that he moved up to Chicago from Florida, and I wanted to help him meet a few clubs. He came out and did a 5-minute guest set and did a great job.

This show was jam-packed and had good energy from the first minute. My cousin, her mom, and a friend came out to this show and it was their first time ever seeing me live. I wanted to put on a good show. For the most part, it went really well. In the middle of my act, I heard a lot of chirping from this older couple stage left (your right). I look over and they are discussing the bill. Fine, it happens. About 5-minutes later I see they are still talking about this fucking thing. I started asking out loud (playfully) “How long does it take to look at a bill? Did you order this? No? Then it must have been me! It’s not complicated shit guys”. They didn’t look up from the bill at all, just kept discussing it while the rest of the audience and myself had a good laugh watching them doing long addition on a short receipt. Turns out, the waitress gave them back the wrong credit card. Which, in my opinion, made the situation worse for two reasons.

  1. It should’ve been even easier to spot “this isn’t our credit card” from the very start, and this whole exchange should’ve been over with, within two seconds.

  2. If they got the wrong credit card, that means another couple in the crowd also got the wrong credit card, and they didn’t give a shit about it.

Oh well, you can’t apply logic to an illogical situation.

Screen Shot 2019-10-08 at 10.31.34 PM.jpg

Saturday 10:30pm Show - We had about 20 people in the room for this show and I was just flat out exhausted. I’m 37-years old and I start to feel my age a bit when those late shows hit. In my 20’s I would do 3-shows a night and still be ready to go out afterward. Now, I’m 37-years old with kids and my body behaves like whiskey dick before the late show. I have to punch myself, and prop myself up until the energy of the show kicks into high gear. The crowd was a lot of fun and I actually for the first time in a long time, did material off of “No Complaints”, “I Plead the First”, and my upcoming album “Vincesectomy”.

At the end of the night, I ended up signing the wall at CG’s. Signing the wall is a tradition at a lot of comedy clubs. It’s like a rite of passage for the performer. Over the years, I’ll eventually make my way back to a club I haven’t been to in a while and see my signature from years ago. It always brings back great memories, and even though it’s a silly signature, I still take pride in being able to do that. So many clubs that I’ve signed the walls of years ago are no longer around. I hope to see my name on this wall for years to come.