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Last year, he made his debut on Broadway at the Helen Hayes Theatre inThe Cottage.
Your role onBad Monkeyimmediately made me think of Guy Who Just Bought a Boat from Weekend Update.
Did you draw on that character as you prepped for this?I can certainly see the comparison.
But no, I like to work.
I do have fun playing a heel.
you’re able to always point to your role inThe Bearas a different kind of person.
I was hoping youd have a bigger role in season two, by the way.
Everyone seemingly gets a second chance in that show except for you.
Doesnt seem fair.You said it, not me, pal.
You should work up an impression.
I didnt have one in time for my screen test, so I didnt audition with it.
And Eric had a look on his face that I based most of the impression on.
We wrote the Update.
It was aFamily Feud,theTrump team versus Clinton team, like Republicans versus Democrats.
Larry David was there as Bernie Sanders with Darrell Hammond as Clinton.Yes.
And Kenans Steve Harvey goes, Well, theyre not.
And then we rose up behind her and said, Yes, we are.
I think that was us calling dibs on those two guys.
Getting to do that two-man with Mikey was just about as much fun as it gets.
How did your show audition go?It took a few tries for me.
I first auditioned in 2013 when I was living in Chicago at the iO Theater.
It was part of a showcase of about 20 people.
The next year, I was living in L.A.
I sent in a tape didnt hear a peep.
The next year, I was also living in L.A. and did a showcase at iO West.
They did not hire me from that either.
And then the following year, I was back in Chicago for some family stuff.
You want me to have a go at get you in the showcase at iO?
You know who was in that showcase?Sarah Sherman before she got it, doing her own thing.
So, so brilliant.
So again, it takes some time for some of us.
So we threw an anniversary party as an excuse to see all my moms old friends.
Shes been looking for you.
So I called her back and she said, Where are you?
Ive been trying to track you down!
Lorne wants to have a drink with you.
So I went into this hotel lobby bar and met Lorne, Steve Higgins, and Erik Kenward.
I just sort of chatted with them all, and they were sort of like, All right.
Well, nice to meet you.
You joined the show weeks before the 2016 election.
What was that time like?That was a pretty heady time.
WhenChappelle hosted the election episode, I got my first piece on the show as a writer.
And then it is revealed that you still live at home with your mother, andyou still breastfeed.
It got a nice chuckle in the room.
Hes got all these incredibly funny ideas, and Im writing it all down.
I didnt even plan to write it because I didnt know how anything worked.
And I was like, No?
I didnt know that Im supposed to.
And she was like, Well, lets just bang it out.
Chappelle threw his own after-after-party.
The Roots played, and Lenny Kravitz played drums.
I want to say Madonna was there, though I never saw her; I just heard.
A Tribe Called Quest was there, and Busta Rhymes got up and did a set.
I remember thinking,This will just be every week from now on.
Amazing.Another vivid memory was when the Cubs won the World Series.
Im from Chicago born and raised and a lifelong Cubs fan.
I can remember Benedict Cumberbatch was the host that week.
You should go say hi.
I was like, Come again?
Thirty seconds later, Dana Carvey walks in again, one of my all-time comedy heroes.
I was like,What is happening in my life right now?
The floodgates open, and I just started to cry.
It was a real pinch me moment.
She goes, Aw, this is pretty big for you, huh, bud?
Theres so many celebrities around, as you note.
The fact that I was still getting to do Eric Trump and Joe Scarborough and all these other things?
I was pretty well taken care of, and I still got to do a lot of fun stuff.
It only brought more attention to the show that I got to be a part of.
So then I got a phone call from Lorne.
Why didnt you stick with it longer?
Terry Fink, the movie critic, was always an Update favorite of mine.
Did you already have that character in your back pocket from beforeSNL?I did not.
So I dont think much from my quote back pocket ever made it.
And he said, Lets do it.
We piled into Tuckers teeny office and watched a few clips of them and wrote our first Morning Joe.
You left the show in 2022 after six seasons.
Everybody leaves at some point.
There was sort of a mass exodus going on.
Theres a right time for everything.
The last couple of years, I mean, it was a hard transition for me.
Ill be honest: I miss the show.
Just getting to do live TV, it feels like being shot out of a cannon.
It sometimes felt like you and Mikey Day were vying for a similar slot on the show.
No, I adore the man so much.
There were plenty of brothers.
We didProperty Brothers, and we didHarry and Will.
Maybe someday well do a special of the brothers.
I felt lucky to hit it off with him right off the bat.
My freshman class of Melissa and Mikey and myself all bonded hard.
I really didnt think like we were occupying the same space.
Its an election year and youre in New York.
Any chance Eric Trump will pop up this fall?You never know!
It would be fun.
Your guess is as good as mine.
