An Interview with Late Night Writer and Vine Legend Conner O’Malley, On His Trump Rally Video

Comedy Features
An Interview with Late Night Writer and Vine Legend Conner O’Malley, On His Trump Rally Video

“Have you seen this?” my friend asked, as he sent me a link to Conner O’Malley’s video from a Donald Trump rally in Orlando. “It’s incredible. It’s also a horror film.”

I knew O’Malley’s name already, mostly from his intense, hilarious Vines, where he bikes up to expensive cars in Manhattan and shouts at the owner. “God made you better than me!” he’ll scream at the puzzled drive. “One thousand years of blood to keep you rich with money!” The comedy is fast, and dark, and difficult to categorize. Mostly, it conveys a feeling of an invisible narrator coming unhinged. There’s anger and envy and a sort of perverted worship of wealth and the American dream—which are so clearly unavailable to him.

The videos I’ve seen were made in 2013 and 2014, before Donald Trump’s candidacy, but the faceless presence behind them was the prototype of a Trump supporter. There was an ache there, a longing for something big and gaudy and unapologetic that would let him forget his own shortcomings and fulfill that national fantasy of superiority. I’ve written before that Trump’s great strength is his ability to make powerless people feel powerful, and O’Malley’s character was a prescient forerunner of his disciples.

What I didn’t know was that O’Malley had since played Trump on camera for Late Night With Seth Meyers, where he’s a writer and a performer. Those sketches are good, but he was made to play one of Trump’s acolytes. Which is exactly what he did in Orlando, taking a camera and director Joe Pera to Trump’s rally on March 5 in one of the worst cities on Earth. Disguised as “Mark Seevers” from, O’Malley nailed the entire scene. My friend was right—the final product was hilarious, but also terrifying. He embodied the pain and desperation and anger of the lost men and women who are currently carrying Trump to the Republican nomination. And while he parodied them, he also seemed to empathize. It’s almost embarrassing to admit this, since we’re talking about a comedy video, but I found the whole thing strangely powerful.

Watch the video below, and read on for my interview with O’Malley, which touches on the dangerous fear-mongering he witnessed at the rally, the process of making the video, and how his own background helps explain his fascination with Trump.

How did this idea come about? What appealed to you about Donald Trump?

Well, I had done some remotes for Late Night that was kinda Trump-related where I want out to Union Square in NYC and campaigned for Trump. And I just kinda wanted to do more of that, so I wanted to go down to one of his rallies. But he doesn’t really campaign that much on the eastern seaboard and he only releases his schedule like five days in advance. So Orlando was a perfect fit.

I’m a big fan of your Vines, and the character you invented preceded Trump’s candidacy, but he seems like such a perfect Trump fan. When he announced he was running, did you see him as someone who fit into your whole aesthetic?

Instantly when he campaigned, when he announced, I was very excited, and immediately wanted to do something about it because he’s such a weird character.

I was in Orlando recently, and to me it’s the worst city in the world, but almost perfect for a Trump rally. What was your impression of the city?

I haven’t been there since I was a kid, but it was so bizarre. It’s really…it’s, um…it’s so gross. It’s just a gross town. And I don’t want to be disparaging toward it, but it’s just…I was reading the Wikipedia page about it and I guess 64 million people come and visit internationally, for Disney World and all the theme parks. And just to think that those people are thinking, “oh, this is what America is like, across the board.” It’s great. Yeah, Orlando is just, it’s truly crazy.

It does feel like America at its worst somehow.

Yeah I mean it’s all chains and souvenir shops. It’s a town that’s just set up for family vacations. When I was a kid I loved it, it was great, it was so much fun and I think maybe that’s what it’s for. It’s not for dickheads who live in New York. It’s for people who have a family and work a job and want to go to a place where they can take their kids and have fun. Outside of that context, it’s like, man, this is very crazy.

Where are you from originally?

I was born and raised in Chicago, on the north side.

The reason I ask is that I’ve found that when people can play an archetype really well, there’s some sense of being able to identify with those people, even though you recognize the absurdity and are skewering them to some degree. I was almost curious if your’e from a working class area, or why you seem so adept at playing that Trump supporter role.

Everybody in my family is an elevator mechanic, or an electrician or a carpenter. They’re all in a trade. My brother Sean was the first one in our family to get a college degree, and it was from ITT Tech. And it was in like, car mechanics. But we’re all super working class, union jobs, fix it ourselves kind of people, and I was the first one who decided to do comedy, go to community college and then drop out.

What’s the family reaction to your career?

They love it, they’re super supportive and really nice. Initially when I started and was just making no money and doing improv shows for no one, they were kind of hesitant, but since then they’ve super supportive.

To some degree you’re making fun of Trump fans, but that’s something about it that didn’t come off as a snobby New Yorker doing it. It seems like there’s a part of you that really understands this.

That’s nice to hear. I was hoping to make it more of an embodiment. Because I do think a lot of people that support Donald Trump just…I think their intentions are in the right place. I think that there was a really strong middle class in this country that went away, and these people, this is their reaction to it.

And I think a snobby attitude is unhelpful. These are people who are in pain, and don’t know how to deal with it. Their pain is finding its outlet in Trump, and that’s one of the reasons beyond the comedy that I loved your video—I think you get that. Even when you sing that song about being rich one day, it sort of speaks to that lost American dream, or something.

Thanks. Yeah, it’s pretty crazy, we’re in a very transitional time. I think that this election indicates that.

Did you completely blend in with your wardrobe, or did people suspect you were a secret comedy agent?

We blended in pretty well. Joe Pera who shot and directed it, he bought a Trump t-shirt, and as soon as we got Trump merchandise, people were super into it, and into talking to us. To start the day off, I had an XFL hat that I was wearing, and people would look at the hat and were a little bit hesitant. So we were like, we’ve got to get a “Make America Great” hat, and after that everyone was super nice. People were nice and not crazy, and they were just very real.

Did you ever feel guilty, that you’re using these people who are being nicer than you thought for comedy?

No, because also once we got into the rally, we figured this is going to be the meat of the video. We shot so many interviews, from nine in the morning until eleven at night for the whole day, and we just had a loose idea of the shape of the video, and then we just kept shooting and tried some different ideas. But at no point was I really feeling guilty. We tried to make the video more like, the joke is on Trump and the joke is on me, and less on these people who are interested in the political process.

Was this your first time seeing Trump live?

Yeah. I saw him walking down a hallway once at 30 Rock when he was hosting SNL. It was weird. But you can tell that he doesn’t know what he’s going to say when he’s up there. And he had a sheet of statistics of who got what percentage in the most recent primaries that he read. And you could just tell that he got up there and was just improvising. He had his stock stuff that he wanted to say, but the pledge felt very spur-of-the-moment, it just came across his head, and it’s like, okay, yeah let’s do this.

And that obviously became a famous moment, with the comparisons to Hitler and everything.

I once saw a comedian, I won’t say who, do an hour and they clearly had not planned it, and they just lost track in the middle of it, and watching Trump was exactly like that. He just came out and had started real strong and then was just like, rambling. He was 45 minutes late, he was tired, it took so long to get in the rally. But he’s also funny. There were parts where he was genuinely funny. He was entertaining. I watched the whole thing, it wasn’t bad.

Do you think he’s so narcissistic that he doesn’t get it, or does he kind of get what he’s doing in some way?

I think he does get it, I also think that he knows exactly what he’s doing. He’s not just like, accidentally…he’s not stupid. He knows what people want to hear and he knows his brand. I think it’s similar, again, to a comedian, who has a very clear voice. And they just get out there and they know exactly…I have stuff in my wheelhouse, and I have this persona, and I’m just going to live it and improvise with it. It was very weird how much it felt like comedy.

How did you feel for his supporters? Because they don’t see it as comedy, or at least not entirely.

The main thing I felt coming away, and the thing I’ve been telling people, is that I 100% guarantee that somebody will be killed at one of his rallies. It was terrifying, it was scary. And there were certain points where I was like, I am in the middle of a hate group. I am in the middle of people being egged on to have the emotion of hate. And it was crazy. The way that some of those protesters were handled and ejected from the rally was very terrifying and we were like five feet from a group of them. They were teenagers, clearly students who showed up and they had signs, and Trump’s people ripped them up.

And as soon as we got there, we clocked them as, okay, they’re definitely protesters. And halfway through his speech they started screaming and they kicked them out. And the force that these adult men used as they moved toward these frail teens was very terrifying. And they were some Black Lives Matter protesters who came down behind him and he was staring at them, and there was one guy that grabbed one of them by the chest super hard, and you just think…I’ve seen street fights growing up, and it was similar to that, the energy was hate and anger.

So it probably didn’t surprise you at all when you saw the punch at his Fayetteville rally.

Yeah, and all it takes is some fucking psycho to bring a gun or grab a gun off a cop. Everything was screened very properly, but it was still scary.

And you felt they intentionally stimulated this emotion of hate? Like, we’re going to make these angry people even angrier?

Before Trump came out and gave his speech, a woman came out and she gave a 20-minute or half-hour speech, and her son had been murdered by an illegal immigrant. Brutally murdered, strangled several times and set on fire, and she gave a very detailed speech about the wounds on her son’s body and how the medical examiner could tell that the rope was strangled and let go and strangled and let go several times, playing with him and watching him die. And the whole arena was completely quiet, and of course I think this woman’s pain is very real, and I think that this is horrible that it happened to her, but I don’t think it’s because of our immigration policies. And it was very much like, this is fear-mongering, this is bringing this woman on and exploiting her and her son’s death to make this audience of people hate immigrants. It just felt irresponsible, it felt like you shouldn’t do that.

And the idea is to get the crowd quietly seething, and Trump is the explosion?

Yeah, which was funny because she gave this very heartfelt speech and the audience was primed for that, and then he was 45 minutes late. The other thing was that during her speech, it was very quiet, and somebody yelled out, “we’re going to build a wall!” And the audience erupted.

The moment in the video where he said, “who’s going to pay for it?” and everybody shouted “Mexico.” I thought your reaction was hilarious, but also not very different from the actual reactions of everybody else at the rally. It’s easy, living in a progressive place, to see it as a joke or distance yourself some way, but then you see that and realize there are tons of people who are true believers. What was it like seeing that?

As soon as he came out, I was acting pretty nuts, but that was nothing compared to the people surrounding us. I blended right in. It’s crazy, I’ve grown up around cousins who are like, “we should fucking wall it off” or say other stuff that’s similar to what Trump is campaigning on, and I’ve always been kind of like, that’s such a dumb idea. And not everybody believes it. So it was pretty crazy to be in an arena with 10,000 people who think that, yes, we should build a wall with one of our largest trading partners.

One of my favorite small moments was at the end of the rally as people were filtering out, you were doing that strange dance in the middle of them. I’ve been a part of groups where you really believe in something, but the people on the fringe who believe it can be embarrassing in a way. And I felt you were playing that character. Did you feel that anyone there was embarrassed by association, that you were taking this crazy energy and blowing it out to these ridiculous proportions?

There were a couple people in front of me who were shooting me looks every once in a while, but what was crazy was that there was another guy behind me who had about three teeth, and he was pacing around back and forth, and everything Trump would say, he’d elaborate on. And he’d be like, “it’s true!” Or he would say stuff that was just insane. There was another guy that had a shirt on that said “anarchists for Trump,” and he would just yell out tag lines, like “Hezbollah too! Fuck Hezbollah!” Just yelling out insane stuff, so I was by far not the craziest person there. It was interesting too to come away and think, his rhetoric is so hot and so inflammatory that there’s no way he can downplay it or come off from it. He will continue to…he’s not going to get the nomination and all the sudden and be like, “maybe the wall is a crazy idea,” and then have his base be like, “yeah, you’re right.” They’ll be like, “what? Fuck you!” So he’s tapped into this crazy group of people.

And you can’t really shut that down.

And they’re not the majority of the people that support him, but they’re definitely the most vocal, and people who have felt shut out of the political process and now have this guy who’s saying all these things that they believe.

I was watching the debate last night, and the post-debate reaction from CNN, they were saying, “oh, Trump was more professional today, and more civil,” and it’s like, fine, but he opened that box already. He could get killed by his own supporters if he ever backed down from this crazy shit he’s saying.

And just remember from 2008, when that woman asked McCain about Obama being a Muslim, and he just shut it down. And that clip is amazing because it really shows McCain being very human and responsible. And being like, no. You can see in his eyes, the change like, “oh, fuck. I have to deal with this.” And there will be none of that with Trump. He doesn’t understand that he’s irresponsible. A lot of people are saying, oh, he’s not a politician, but it’s like, politicians are smart as fuck. When they’re saying something, they’re thinking, how is this going to bite me in the fucking ass 20 years from now?

How could I ruin my legacy or destroy my dignity? Which are just not concerns for him.

Yeah, or like Obama saying, I’m evolving on gay marriage. It’s the ultimate political answer, that’s saying, I’m supporting it but I need you to buy me some time. He doesn’t do that.

Some people are saying that even if he doesn’t win, he’s made it okay for the next person, who could be the really dangerous one. Now it’s legitimate not to worry about decorum. I also want to ask you about the ending sequence, going by the machine gun stores, and the voiceover segments. Was that planned?

It was, we did want to go Sea World and we wanted to go to Epcot, purely because we spent so much money to get to Orlando, and we better milk everything we can get out of this. It was planned in that sense, and we had a loose idea that we’d end it with this voiceover narration part, and just take advantage of Orlando, and all those beautiful sites. We wanted to get into Sea World, but it was closing in an hour, and we drove to Epcot, and people who worked there were like, “you don’t want to buy tickets, it closes in a hour.” So it’s like, okay.

The funniest moment of the whole thing for me was when you told those guys in the interview that your stepdad had locked you in a cage for a week. And I just loved that look when people are all into what you’re saying, and you add a new piece of information and they just have no idea how to react. How were those interviews in general?

We had this whole narrative that I wanted Donald Trump to adopt me as his son. Make eye contact with me, and touch me. But we had to cut all that. We just tried to build a little bit of character backstory so it felt a little bit stronger than just a straight-up man on the street piece, so it had some narrative arc to it. And it would pay off with the Orlando footage. But yeah that one part when I said that cage line, there’s a guy that laughs and then catches himself. It was pretty great.

And this was just for your YouTube page?

Yeah, just uploaded it to YouTube. I just wanted to do it on my own.

Last, I have to ask you, as a fan of your Vines, how did they start? I always find myself wondering how the hell that evolved.

When I moved to New York I got a job as a dog walker, and I had a route where I would go from dog to dog on a bike. And my route was from Little Italy to 92nd Street. And I was riding down Fifth Avenue and I would see people with their hands out trying to hail cabs and I thought it would be funny to do a Vine of me trying to high-five them. So it started like that, and just being from Chicago, you never see people in suits on the street. So I would see all these businessmen, and I thought they were funny. So I just started interacting with them, and then you see Ferraris on the street, and I’d be like, fuck! I remember once me and my brother saw a Ferrari in Chicago, and we talked about it for like, six months afterward. So just seeing all these fancy cars, it was like, fuck, I should just go up to them and talk about how cool their cars are. So it was just kind of a slow evolution that wasn’t planned out or anything like that, and I just started doing it, and kinda figured I’d do one every day.

There was one where a guy seemed to be attacking you. Did anything horrible ever happen?

That one was staged. That was my brother Sean, and that was his Mercury Grand Marquis. I always planned an escape route that was down a one-way the wrong way, and I was always on a bike so I could get away real fast. And the thing about doing it in New York is that you see so much crazy stuff throughout your day, and like half the time you wouldn’t even tell someone about it at the end of the day. So it’s just a barrage of crazy shit going on, so people’s tolerance for interactions on the street is so high.

And I would also kind of see them, see who they were, and try to find them out a little bit beforehand. It takes a coward to catch a coward. Also, if you think about it, by the time it’s over, the person is going, “what?” It’s a seven-second Vine, and their interaction is three to five seconds of it. It’s so fast that by the time it’s over, they don’t know what just happened.

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