Derek Sheen to record live album at Chicago’s Comedians You Should Know on June 24, 25

Because of Derek Sheen, I will never again think of an escalator as an escalator.  Instead, I will take the “wizard stairs.”  Thanks to this Seattle-based comedian, the next billion times I say something in some mortifying way I didn’t mean (and believe me, those billion times all are likely to occur by next Tuesday), I will not mull over my slip of tongue.  No.  I will envision my errant word “taking the emergency staircase and shoulder checking” the word I’d actually intended.

Derek is a master of energetic comedic storytelling with nonstop, vivid images that will permanently alter and improve the way you see the world.  His material fearlessly covers everything from his own worst embarrassments and aggravations Derek Sheen phototo the intractable problems of racism, religious fanaticism and people who make the world hell for other people, all described with the verbal flair of an artist.  Magritte, Dali and Robert Crumb could take notes.

You can hear Derek record his second album this Wednesday and Thursday nights, June 24 and 25 at Chicago’s famed Comedians You Should Know (more details below).  Venues around the country vied for the privilege of hosting the recording, but CYSK emerged the victor.

This event will be Chicagoans’ only opportunity to hear Derek’s new album material live.  Patton Oswalt, who is both a fan of Derek’s and a mentor, advised him never to repeat material once a project is done.

Derek has been a comedian for eleven years. In that time, he’s gone from a rocker who tested his stand-up chops at band rehearsals to becoming a headlining comedian all over the country, including at the Bridgetown Comedy Festival, San Francisco Sketchfest and Cape Fear Comedy Festival.

He regularly tours with Patton Oswalt and Brian Posehn.  His debut album, Holy Drivel, is the only comedy album produced by metal engineer Matt Bayles (Mastadon, Pearl Jam).    His second album will be produced by Dan Schlissel’s Stand Up! Records whose discography includes Patton Oswalt, Maria Bamford, Hannibal Buress, David Cross, Marc Maron, Kyle Kinane, Joan Rivers, David Heti and a long list of other comic luminaries too numerous to name here.

Derek kindly took time out in the busy days before getting on the plane to Chicago to talk about his comedy roots, how he learned to take down bullies in unexpected ways and what it’s like to work with the comedy greats who first inspired him.  Following is an edited transcript of our phone conversation.


Q: How did you decide to record your album in Chicago?

A: I had the opportunity to record in so many good cities. San Francisco, New York, Los Angeles, Austin.  But I had my heart set on Chicago.  I love the comics and the audience there.  I’ve always had good shows there and any time I’ve gone to Chicago to work out material, it’s always been such a blast.  There’s so much fellowship and everyone is so nice.   The audience is smart and the comics are rad.  When I looked at all the places I could go, Chicago felt like my second home. So it was a no-brainer.

Q: How did you choose Comedians You Should Know?

A: Michael Sanchez (of Comedians You Should Know) reached out after I put some feelers out to Chicago.  Beat Kitchen came up, too, which I love a lot.  It’s also a great venue.  Michael offered me Comedians You Should Know and the dates we wanted worked out really well with them, so we went with them instead.  I love that venue.  I try to do a show there every time I come through Chicago.  It’s perfect.  Low ceilings.  Very intimate.  It’s packed.  It feels like you’re in a major theater.  It’s just such a great place.  The audience is very smart.  It’s definitely a destination place for stand-up.  So I was very happy that we were able to get it and I was so happy that the guys with CYSK were so gracious to give us the space for two days.

Q: What is the week before the recording like – what do you do to finish preparing?

A: The week before is a lot of second guessing.  I booked a week of shows.  I’ll run through my set and double check everything.   The weekend before I leave for Chicago, I’m planning a last minute living room show with family and friends.  I have a few bottles of wine. I have a comic opening for me in the living room and I’m going to run through the entire thing.   Then I do a variety show in town and then I fly out. I’m so happy with the material I have right now.  I’m excited to do it and get it done.

Q: How did you get started in stand-up?

A: That was my mom’s fault.  My mom had just an awful childhood. So her big thing was she would rather have laughter in the house than anything else.  She would go to the library and grab armloads of comedy albums. There was always stand-up happening in the house.

Every year for my birthday she would rent Lenny Bruce’s Thank You, Mask Man.  I didn’t even know what it was.  I just thought it was a cartoon.  It was her birthday tradition.   I grew up listening to Dick Gregory, Mort Sahl, Nichols and May, Phyllis Diller and George Carlin. There was never any music in the house.  It was always stand-up.

Q: I noticed at the end of your first album, Holy Drivel, when you thanked your mom it was so heartfelt. 

A: Oh yeah, she was right there in the front row.  It’s hard to do stand-up in front of my mom because she is so smart.  Growing up I saw the happiness stand-up gave her.  It made me want to do it even as a kid.  I wanted to keep that momentum up.  To this day in the back of my head, if I can make my mom laugh then I’m doing it right.

There’s something transcendental about natural laughter. My mom calls it whistling through the graveyard.  In the horror of an abusive childhood you have to find something to laugh at or it will eat you alive.  So she would find little things.  That was her lesson to me as a kid.  Whenever you feel scared or terrified, find the weakest point of that thing and make fun of it and it will instantly cripple it.  Whether it’s a bully or an anxiety, make fun of it and it will crumble.

It really worked. Whenever I was picked on, I would find something about that person that was embarrassing or something funny about what was happening.  I would call it out and it would usually stop them right away.

Q: What a great thing to teach kids how to do.

A:  It can save your life.  I made friends with most of the guys who wanted to bully me. I could disarm them so easily by making them laugh or making them feel ludicrous about what they were doing.  I was unusually small for my age and I would tell them, “I know you hate me, but there’s no way you could hate me more than I already hate me.  Just remember. Every time you hit me, I feel better about myself.”

They would say, “Oh my god, you’re crazy.”  And I’d say, “I am. I’m very crazy.  I’m full of anxiety and self-doubt and all you’re going to do is reinforce that.”   I shocked one bully who wanted to beat me so bad.  I just went into a hug and said, “Thank you.” We ended up being friends all the way through high school.

Q: You were a brave kid. 

A: You know, I think it was also that my dad was also not kind.  It was more of a survival instinct than anything else. I didn’t see the risk in just walking right into it because I figured most of the time if you do that, it’s not fun for anybody.  You’ve removed the challenge.

Now that I reflect on it, the thing that got me into fights was standing up for other people who were bullied.  It was the one thing I couldn’t tolerate.  Coming after me was one thing.  I get it.  I’m tiny and I can defend myself.  I can use my brain or as my mom calls it, “tongue fu.”

Seeing somebody else getting picked on was my trigger.  It still is.  It inflames me and I usually get involved.  So those were the only times I got into trouble as a kid, but it was usually for a good cause.

I think it’s what happens when you grow up in a house where there is abuse and you’ve got somebody else who has suffered through it. You’ve got to find some way to cling to your sanity.  Sometimes it’s humor, but you’ve got to find a way to let all that anger out.  So I would put myself in others’ situations. I’m sure psychologically it was a way to get the anger out of me.

In my adult life, I can see the danger still there.  I find myself going after things that are indefensible.  I find the bully in that thing that pisses me off and that’s the thing I usually attack.

Q: I noticed that you take on topics like racism and homophobia and you do it with a warmth that draws the audience closer and makes people want to listen.  What is the art of hitting that note? 

A: I think part of it is presenting your idea with fallibility.   What drives me nuts with a lot of comics is they beat you over the head.  Even as a kid I hated being talked at.  It always made me feel like you’re telling me what I think and I don’t have a choice.

You can’t change people’s minds like that.  All you’ll do is alienate them or make them feel stupid and that doesn’t fix anything.  My whole life I’ve always tried to let people know I don’t know shit, but I have some ideas.  If you discuss ideas with the audience, not at them, people don’t feel they have to have their hackles up.

I’ve gone to the south and done all kinds of crazy shit in front of red audiences.  Talking about the bible and the crucifixion and how I think things are wrong. I present it like “this is a thing I’m thinking about.”  Most of the time it gets people on board instead of angry.  It’s huge to hear people in the Bible Belt say, “I don’t agree with you, but that’s a good point.”  Much better than the quiet seething acrimony that can happen with an audience that doesn’t agree with you.

Comedy is a great tool for communicating because you can talk about serious issues, but you’re putting the medicine in a treat and wrapping it in something delicious.

Q: Within the writing itself you draw pictures with words that are really fun to listen to.

A: There’s a lot of that on this next album.  It’s visualizing the thing.  I have pictures in my head that I think are really funny.  They are visual notes.  It’s trying to describe it with the least amount of words, the most amount of vision and the right rhythm.

It can take months to chisel away at something to make it work.  It’s like crafting a song.  You want a hook and a melody and it has to fit rhythmically without being too obvious. I’m very particular about word choice.

I like to craft things that you can listen to four or five times and hear something different in it each time.  I like to put in little Easter eggs and make the longer bits fun so that when you do listen to them again, the ending is not the best part.  The middle is the best part.  The ending is just the cherry on top.

Barry Blankenship, who is doing my album cover art, is designing the back cover with old stand-alone video games whose titles come from the colorful phrases in my material. I forgot I had so many of those. [Note: Barry Blankenship is a Seattle artist known for his comedy album art and posters.]

Q: You mentioned music.  You were a musician and also worked with King Crimson’s Trey Gunn. How did you go from music to comedy?

A: I worked with Trey quite a bit as a tech and as a roadie. Once, I drove all the way back from Mexico City to Seattle with the band with only two of us on the crew.  We did all the loading and all the tech.  They were some of my favorite moments of my life.

At the time, I was starting to dip my toe back in the water [of stand-up]. I’d attempted stand-up several times and I always backed out of it after a few weeks because I got so intimidated and I didn’t think the time was right.  I didn’t feel like I was in that place where I could be funny yet.  I wasn’t able to write.  I felt like, “I don’t get it.  I don’t have the hang of it.”

So I started playing music again instead and working with bands, writing and doing production, just to keep me busy.  I just wanted to be on stage.  I wanted to be out performing.  I felt like if I could keep doing that I would be working that creative muscle.

When I got back from Mexico City, I quit my job at Guitar Center and went to work at a smaller shop with a friend of mine.  I was also playing in a band.  I went from three hours of rehearsal and five minutes of my talking on stage to two hours of rehearsal and one hour of me talking.  It got to the point where I’d be talking on the rehearsal stage for two and a half hours.

Finally, I said “Guys, I need to be honest. I need to get out of here and do this.  I think it’s the right time. I’m comfortable on stage.  I’m not scared anymore.”

Then I went and I did stand-up and had to re-learn everything including being on stage.  Stand-up is such a deceptive thing.  Doing it right makes it seem like it’s just getting on stage and talking, but it is terrifying.  It is years of soul-crushing, anxiety-ridden … it’s very deceptive.

Q: How do you work out your material?

A: My brain is a wonderland of scary and ridiculous shit. I’m not sure what the process is all the time.    Last night was a great example.  I was on stage and having so much fun.  I realized halfway through that I had just instantly fixed a problem.  My brain said, “Say it this way” and I realized, oh shit, I just solved a major problem with this thing.

Luckily, the guy who booked the show said, “I hope you don’t mind that I audio recorded it for you.  I can send it to you.”  And I was like, “God, would you please?”   There were three times during that set where all of a sudden I just problem-solved and a joke landed better and hit better.  And I thought, “Thank God this is happening before next week.  I don’t know how you’re working, brain, but thank you.”

Q: What is your advice for writing jokes that land?

A: You can always be funny in front of your friends but it’s so much harder in a room full of strangers.  It’s easy to get your friends on board.  They’ll let you get your thoughts together and they’ll go with you because they’re your friends. They’re already invested in you. It’s so different when you get on stage because now it’s not a free zone.  It’s a battlefield.  And you have to fucking be ready.

But that’s the beautiful thing about failing.  Failure teaches you over and over again, if you’re not insane, to figure out the things that were part of that failure and fix it.  That’s what open mics are for.

When I’m working on material, I’ll go back and take a word out or put a word in or change the timing.  I might lower or raise my voice or change the dynamics. You have to keep going back to find out where the laugh is.  Then when you get one laugh, you’re like, now I need to capitalize on that.   Let’s work on another part of it and see if I can get two laughs.

It’s an arduous process.  But it’s so worth it in the end if it works right.  There’s no better validation.  It’s not the laughter.  It’s the validation.  It’s that people enjoyed what you did.  That to me, is the pay-off when they come up afterwards to say “that made me feel so good.”  Or when people still have tears in their eyes because they were laughing.  You think, “Wow, I did that.”

You keep progressing through every failure. Then, hopefully, the failures become smaller and smaller until they’re just personal misgivings and not major fuck-ups.

Q: What is the craziest or best thing that’s happened to you as a comedian?

A: in 2005, I saw Patton Oswalt at Bumbershoot [Seattle arts festival]. I had just discovered his first album, Feeling Kind of Patton.  It was a game changer for me. Everybody had told me that comedy has to be “Set up, punch. Set up, punch.” That’s what comedy is.  It’s one liners and premises. You get in, you get out.  Jerry Seinfeld your way through it.

Then I heard Patton and he blew my mind because I realized I can talk to an audience and have fun with stuff.  It’s not just about regurgitating your thoughts.

After Bumbershoot, we went across the street to a bar and he was there having a drink.  I went up to say hi to him and I bought him a drink.  A little while later, he kind of crawled over the high bench back to sit with us and introduced himself again.  He’d had a bunch of whiskeys. I told him how big a fan I was and then we got hammered on more whiskey.  Eventually, his manager pulled him out of the booth and said, “Okay, we’ve got to get you back to the hotel, buddy.”

He said good night and I told my wife, “My goal, I don’t know how long it’s going to take, but some day I’m going to open for that guy.  I’m going to get good enough to open for him and that will be when I know I’ve made it as a comic.”   Really I thought it was just one of those pipe dreams.

In October 2012, I got the call from Dave Rath, his manager, that Patton is doing a small tour and would I mind opening for him? And I shit my pants.  I was like, “Oh my god, the thing that I’ve always wanted to happen is happening.”

So I opened for Patton on a bunch of theater tours and we did a casino together and that story ended up on his last album. I opened for my hero and now I open for him regularly.  He’s been a great friend and a huge help as a comic.

He introduced me to Brian Posehn and now Brian is a friend of mine.  I’m going to open for him for the recording of his special.  All these amazing things I never thought would happen.  To me, that’s the craziest thing.  The  people I was most influenced by, I now have this opportunity to watch them every night from backstage when I’m on tour with them and it blows my mind that I’m in that place.

When it happened I told myself, “You can’t stop working now.  You have to put it into overdrive because you cannot disappoint anybody.  Now there are more eyes on you.”  The last thing I would want is for someone who I put on a pedestal, someone like Patton or Brian to go, “Eh, that stunk.”  So now I really have to work my ass off and make sure I make those guys proud.

Their audiences have been so supportive of me and to me, that’s the craziest thing because I didn’t earn it.  I had friends who helped me get to that place.  It wasn’t just hard work and perseverance.  It was definitely guys who were at a bigger level than me who helped me up a rung, so I make sure I do that for other comics.

Q: What’s the best advice you’ve got from Patton Oswalt?

A:  Don’t rest on your laurels. Always be working to improve. And no matter how shitty you are at the business side of things, get good at it.  Because you have to be.  Also, he told me to burn all my material every time I put out a project which was great advice but also terrifying.  But it forces me to work.  It forces me to write all the time.

Q: And from Brian Posehn?

A: Brian’s best advice to me was don’t forget at the end of the day that this is supposed to be fun.  If you start feeling the pressure that you have to do something or be something, then that’s not what this is for.  We’re doing this for fun.  He also told me not to fuck up.  Please don’t fuck up.

Q: When you come to Chicago is there anything that you always have with you on the road that you’ll be bringing?

A: The one thing I’ll probably bring to Chicago is the sense that it could all fall apart when I get there and I just have to persevere.  That way, if it all goes well it’s going to be an incredible bonus.  I’ll work fine if there’s failure.  I can work around it.  That’s fine. But if things are a success, it’s an even bigger surprise for me.  So I’ll go to Chicago with a complete lack of self-confidence.

I’ll be with my friends.  We’ll probably have a couple of bottles of wine over the course of the weekend and I’ll just try to do the best I can and make sure that the audience digs it and that I don’t blow it because you only get one shot at first impressions, but you get several shots at several other impressions. I’d rather knock it out of the park the first time.



You are invited to Derek Sheen’s live album recording at Comedians You Should Know, June 24 and 25.  The show begins at 9:00 p.m. (doors open at 8:00 p.m.).   Comedians You Should Know is located at Timothy O’Toole’s, 622 N. Fairbanks Court, Chicago. (312) 642-0700.  Tickets are $5 online, $10 at the door.  For tickets:

For more about Derek Sheen, check out

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