First of all, any upcoming projects you want to talk about?
The closest thing is my New Netflix special I did last November – Bones and All. That was my third Netflix special. I’m working on new stuff now and am ready to get out there again.
To be fair, that last hour I did the critics said I proved that I was the best joke writer, but they wanted to know what else I could do. I said “No. I like doing this – this is what I do!”
How did you get your start in this – and what would you say to others trying to do the same thing?
I didn’t set out there with a plan. I figured it out as I went. I didn’t want to go home after college. I went out to L.A. and struggled and got retail jobs. I didn’t go to L.A. to be a comedian – I thought I would be a writer for a comedy show. I just knew I could do comedy for free on my own and work on that at night.
Would you want to go into acting at all?
I enjoy the writing and the effort that goes into comedy. There’s less effort then having to go and act. If there was a two day acting job I’d say yes but I’m usually on the road so the timing usually doesn’t work. I also don’t want to get locked in to a seven-year sitcom.
I’ve worked on scripts and played some parts on shows – but it has to work with my schedule. I have a friend who wrote a role for me on Hacks but I couldn’t do it.
I’m surprised I don’t get more voice-over offers though. I think I have a good voice for that!
Now, I’m doing my dream job. I’m reading books I want to read and doing jokes every night – practicing those with friends. I love that life. Performing at Carnegie Hall and the Sydney Opera House – those were huge deals for me. I want to continue doing that.
Did you have any mentors or influences that helped shape your career?
I kept my idols at a distance. Jack Handey and Steven Wright were two guys I really followed.
Jimmy Brogan – he went to college with my dad at Notre Dame. He told me that I just needed to do standup while I waited on my writing career. Just to keep working at it. I wouldn’t have done it any other way.
What was your family’s reaction when you told them you want to be a comedian?
That’s a good question. It went from shame to pride over the years. No parent wants to hear that their kid is going to be a comedian.
I waited two years into my journey to tell them – it was still embarrassing. I was happy with my progress then but I wasn’t a big name. It wasn’t until I was on TV and writing for Jimmy Fallon that it got better. Now when they tell people their name, people say “Oh, like the comedian!” – they love that now.
What was plan B for you?
Plan A was to be a jokewriter. I wanted to write for late night shows like Fallon. I knew a lot of comedians and they all had a dark sense of humor though that didn’t always come out in their comedy. I would write jokes but they were so dark they wouldn’t tell them. So I figured I would do my comedy using jokes that were so dark only I could tell them.
And at the end of the day, I’m really just too good looking not to be on stage!
How do you deal with pushback for those who feel the humor gets too dark?
I don’t let it bother me. It’s like a horror movie – some people watch them through their fingers and hate it. If people complain in the moment, they’ll get over it. As an audience member, I think they enjoy watching others not enjoy it.
And at this stage they shouldn’t be surprised at your comedy…
When I was 23 yeah they wouldn’t know what to expect – I feel bad for these people then. But at this point it’s your fault – tickets are expensive – you should know what to expect.
Do you like writing or the standup more?
Coming up with the jokes is the fun part. It’s like being a chef – then you enjoy watching people enjoy the meal. I like watching the audience to see what works and what doesn’t. Most of the time I think a joke will be great and I’m wrong. I find that interesting.
How do you get the guts to go on stage and work on jokes like that?
You have to be stupid – and desperate. I couldn’t do it now like I could when I was 22. If fear was keeping me back I had to get through it. You get better each time you do it. I’d stutter through my set the first time but get better each time. Not being afraid isn’t an attribute. Being nervous still before every performance is why I am good.
What was the biggest moment for you in your career – the thing that impacted you most?
I had a lot of failures and successes. We all do. I think the biggest thing that was the beginning of big things for me was the Donald Trump roast. I know they edit it to look good no matter how good you do, but the people there will know if you couldn’t make it. But I knew life was going to change for me after that.
Why?
I was an absolute surprise – no one knew who I was. They didn’t expect me to be that dark. I was worried that I wasn’t going to be as mean as Jeffrey Ross or Lisa Lampanelli so I worked hard to make it extra dark. I over-corrected! But I had the set of my life. That was a big moment for me. I’ll still watch that roast. And it was nice to get the Donald Trump jokes out of the way before the world went crazy. I got to get the jokes out long before everyone else.
Were there moments where things didn’t work out – tougher points in you career you can share?
I’m not shy about failure. I’m mentally healthy. When something goes wrong I make sure it’s not the end of my story.
I auditioned to be a weekend anchor for SNL’s Weekend Update and thought I had a phenomenal tryout for Lorne. I thought there was a good chance I would get it – but I didn’t. I waited for that call but I didn’t get the job.
I was upset but I didn’t let it become the end of my story. I just decided that the next special I did was going to be so good that I would be glad to not get the job.
And Michael Che and Colin Jost have done it longer now than anyone. It wasn’t about them – it was just a moment where I needed to figure it out. Things like that happen all the time.
As a Pittsburgh guy – did the city have an effect on you and your comedy? How so?
Certainly. I never started off in the Pittsburgh comedy scene. I went back to perform after I became a name. But the Pittsburgh work ethic – my father instilled that in me.
Every day I could spend five minutes on stage – but I could spend the rest of the 23 hours and 55 minutes writing. That was a Pittsburgh thing to do. I never sweat on stage – the sweat was all behind the scenes. The writing is my favorite work – it’s like being in the mill. And that’s a Pittsburgh thing.
Are there people you really enjoyed working with the most?
I liked everyone I worked with though I keep a distance from most. Norm McDonald – we didn’t get along. But it was fun trying to figure it out. Spending time with someone that different was interesting.
What made him so different?
Everything about him was different. He was making a comeback at the time and was showing up kind of out of nowhere. Roseanne, Keenan Ivory Wayans – they were fun to work with. But Norm – it took a couple of episodes to figure out how to work with him. I wanted it to be a bit combative with him and it took time for it to work out.
Are you a Pittsburgh sports fan still or have you converted to being an L.A. fan now that you’re living out there?
I’ve lived in L.A. now longer than I’ve lived anywhere else. But I can’t get into the Kings. The Pens and Steelers are still my teams – I’m a fan for life. I tried to be a Dodgers fan, but God help me I still love the Pirates too. At least we have Skenes!
Have you had any encounters with any of the Pittsburgh athletes?
No never. I hear other comedians who have talked about visiting the teams but I haven’t done that. My dad threw out the first pitch at a Pirates game once and I caught it for him, but none of the players came up and talked to me. I’m not even sure they knew I was there. I did get to talk to Hines Ward on a podcast and met Troy Polamalu when I was writing for Jimmy Fallon. That was a highlight for me.
There’s no players I wouldn’t want to meet. I was at the same restaurant as Mario Lemieux once, but I didn’t want to go up and bother him.
What else makes you tick outside of comedy?
I think making people love reading and literature. I would love to get more people get into books – to promote reading. There’s a power in that – the world is losing its empathy. Literature helps give you empathy – you walk a mile in someone’s shoes through novels.
So maybe I can write a book or do something to make books cool again. People are too into their screens. I hope the next generation rejects that and reads more.
I’m 46 years old. My cool power is limited but I still have my leather jackets and want to try!
I also like reminding people that I am from Pittsburgh. I’m an Upper St. Clair grad! People think I’m from L.A. – I don’t have the Pittsburgh accent. I could not be more Pittsburgh born and raised!
Do you talk sports and hang out with other Pittsburgh guys out there in L.A.?
Steve Byrne and I will talk Steelers and sports when we see each other. Holy God, I hoped we didn’t get Aaron Rodgers! But I haven’t met Dennis Miller or Billy Gardell yet – I’d like to. It’s just hard because we’re all traveling and doing our things.