Q&A: Five Questions with Saturday Night Live Star Colin Jost

Kenan Thompson as David ‘Big Papi’ Ortiz and Colin Jost Photo by Dana Edelson / NBC

Like the rest of the world, Saturday Night Live star Colin Jost just can’t seem to peel his eyes away from the utter mess that is this year’s presidential race.

The Harvard alum turned Weekend Update anchor, who’s set to perform in front of sold out crowds all weekend long in Boston, has had the privilege of working alongside several candidates on SNL this season. Out of all the presidential hopefuls, Jost says that Republican frontrunner Donald Trump brought the “best entourage” to the show.

“The best entourage was Donald Trump because he had zero people,” Jost says. “He had no advisors, no friends. It was fascinating. It was like, ‘Ok, cool.’ You could just walk in and talk to him. That was surreal.”

Check out what else Jost had to say about Trump, coming back to Boston, and more.

You’ve spent a lot of time in Boston over the years. What do you like to do when you come back to town?

It’s nice to be there in the spring. I’m hoping it will basically be spring, we’ll see. It’s weird, every time I come back I’ll see new areas. Last time I went I hung around the North End, which I haven’t really been around since college, and that was cool. Just go there and wander and eat a bunch of good food. I’ll probably try to explore a little bit, see another section of town that I haven’t seen in years.

Of course you’ve been covering the presidential race on Weekend Update. How crazy has this election cycle been?

Now, I’m just curious about what’s going to happen on the Republican side. I still wonder if Mitch McConnell is going to rig something up where there’s another candidate who runs against Donald Trump. I don’t know what the convention is going to be like, there might be a weird curveball still where someone else comes into play.

Taran Killam, Donald Trump, and Darrell Hammond Photo by Dana Edelson / NBC

When I spoke to Jay Pharaoh he told me that Hillary Clinton brought a bigger entourage than Drake to her appearance on SNL. Out of all the candidates who’ve stopped by the show, who had the best entourage?

The best entourage was Donald Trump because he had zero people. He had no advisors, no friends. It was fascinating. It was like, “Ok, cool.” You could just walk in and talk to him. That was surreal. But I don’t know. Bernie Sanders’ people were also super nice and there was a real fun energy when he was there. People were clearly excited to see him, so it was good.

What’s the most cringeworthy moment you’ve had on stage as a stand-up comic?

They were like yelling from the back and then I basically made fun of the person who was yelling things out in the middle of jokes and everything. Later, someone told me that the person basically had a mental disability and I was like, “Oh Jesus.” But you don’t know because you can’t see who the person is and they’re just interrupting jokes. There are times where you have to feel it out and sense that person might actually have something else going on, or is so drunk that if you engage them, they’re only going to get worse.

Who would you put on your comedy Mount Rushmore?

I can say four? I don’t know, that’s a pretty hard one. It’s like choosing your best cast for SNL. It’s kind of a complicated question because there’s a lot of people you want on for different reasons. I’ll say all of the comedians. Get everyone on there right? Even if you’ve done five minutes at an open mic, you’re on there. That’s the perfect millennial Mount Rushmore.

Colin Jost performs at Laugh Boston Friday, March 18 and Saturday, March 19.

This interview has been edited and condensed.