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Sean White has released one of 2015’s most critically acclaimed stand up albums, Dead and Gone, on AST Records. The Chicago Tribune called it “an essential rumination about loss” and it was included in The AV Club’s Best of 2015 so far roundup. He’s not a fan of Butterfingers. -ed.

My first road show with other Chicago comics! Woohoo! We get to ride in the same car together and I get to actually get to know two comics I really liked in the scene! I hope I don’t say anything too stupid and we all get along! This night, about 4 years ago now, was the worst night of my career.

I performed in a bar my first year doing stand-up in Statesboro, GA that was supposed to have trivia that night. No one was informed of the schedule change and they chanted, “You suck, get off the stage” in unison despite technically being on different teams. Their hate of me united them. My first Chicago road show was worse.

Insults rarely bother me. Feeling helpless cripples me. Pain is easy to understand, helplessness is not. That show in the middle of nowhere shook my confidence more than any other show to date.

It was a show in a restaurant booked by a very nice person and so I would like to state I do not feel the show was a reflection of him as a booker. Shit happens. Krains Butter is his stage name and he had booked Megan Gailey, Joe Fernandez, and myself out in the middle of nowhere. My picture was even on the flyer! Me! Next to them and finally starting to do shows that paid!

Strike 1: The Drive

Joe drove. I met them in Wrigleyville and we began the trip. Quiet at first, I started trying to make conversation. As Joe was scream singing mo-town while maintaining eye contact with me, I decided to try and talk to Megan. That ended with her saying something I’ll never forget, “You’re ruining sarcasm.” Needless to say, things weren’t going well. This was my first experience sitting in a car for hours with people who literally could not understand anything I was saying. The rest of the drive consisted of me retreating in my head and wondering how bad jumping out of a moving car really feels to see which is worse. The comment wasn’t meant maliciously and I understand that and frankly it helped me learn more about myself and how I talk to strangers. Poorly.

Strike 2: The Room

To fully describe the beautiful space we were to perform in, I present you with a crappy paint drawing of it below (Wes Anderson Side Boob Style). We performed upstairs between the bar and the only method of reaching the upstairs. Entry required you walk in front of the comic. The stairs were two flights and after the first steps there was a flat area with 4 tables and audience. That’s right, if someone went up they blocked them not once but twice. Also all food orders were carried this way..Bathroom? Also directly behind the comic. Wanna pee? PLAY THROUGH. Wanna drink? PLAY THROUGH. Want a quiet spot? Don’t worry, the main audience seating area is over the 15′ stair gap! So you tell jokes with drinks being served 1 foot behind you, over the stair hazard, in direct conflict with food serving, AND in the way of the bathroom.

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Strike 3: The Show

Krains hosted. He knows his crowd so while it was nothing spectacular, he did fine given the room. I was first, then Joe, then Megan. My mother and one of my sisters had just passed away and I was realizing that I was almost certainly heading for a divorce as my now ex had given me a Butterfinger for my birthday. One. No, not king size. I don’t even like Butterfingers. I was trying to redirect this pain through my comedy and as I was not divorced yet, only had a few jokes about my family members passing.

I tried to OPEN with some of the darkest material I had ever written in a time when I had almost zero separation from the subject, no experience with dark humor, and after only a week of practicing them. That’s a smart move, right? Turns out the elderly and very obese audience did not agree. I bailed on those jokes about 3 minutes in and tried to go back to my old stuff, “Oh man am I SUCH A NERRRDDDD!” Turns out, uh no good way to transition from really bad death jokes to confidently told really bad nerd jokes. Double bomb. I could see the disgust on their faces, or at least my own reflected in their shiny jowels.

Joe goes up and while the audience as a whole doesn’t quite get him, he does well.

Megan absolutely destroyed. Like to a point where it was conceivable that the audience might carry her out as some form of new local queen. She deserved it. Her crowd work was spot on and she was extremely likable. That’s the thing though, I was a house comedian at a club for two years where I did nothing but crowd work. I should’ve been able to read the situation and see that crowd work was the only way around the room obstacles and relation gap. I was supposed to be better than that. I didn’t deserve to talk to them, the audience or the booker.

I waited for the audience to finish congratulating Megan and Joe while avoiding me. I have no recollection of the rest of that night. It’s been blocked out like most nightmares.

At one of the lowest times in my life, stand up was all I had. I was losing my family and friends and needed to reach out. I failed in the car and I failed on the stage. I have never felt as lonely as I did in that moment.

Photo by Anthony McBrien, Honk Honk Photography, courtesy of Sean White