It takes a certain kind of individual to punctuate the banality of press junkets, where actors and actresses are trained to hurl platitudes about “what it was like” to work with George Clooney to fawning journalists. After being contractually obligated to sit and respond to uninteresting questions, it’s no wonder tedium tends to nestle in. Both parties—the reporter and the talent—eventually find themselves mired in mind-numbing ennui.

And then you speak to someone like Kal Penn, the now 38-year-old actor known for being one-half of the weed-infused, Harold and Kumar franchise. Aside from his amicable demeanor, Penn is sharp and thoughtful in conversation. From the moment we sit down he comes across as someone interested in genuine engagement. There’s no pretense about Penn. Like any normal dialogue with another human being, there are unrehearsed stops and starts, sometimes taking a few moments before answering a question.

When he sat down with Playboy at the Toronto International Film Festival on behalf of his latest movie, The Girl in the Photographs, he spoke candidly about the joys of being Kumar, working in the Obama administration, and the inimitable Donald Trump

Let’s start with UCLA.
I liked it, it was pretty fun. I started as a theater major. Theater and film, then, like everybody else, probably changed like ten times before I ended up in sociology with a specialization in film, theater and television.

And what did the transition from college to the film business look like?
I went to UCLA to pursue mostly film and theater, and then just spending years and years working odd jobs and trying to get your foot in the door.

What were the odd jobs?
The worst was telemarketing, which I only lasted two days, I think.

What did you have to do?
You had to call old people and convince them to donate money to some bullshit organization, it was awful. I don’t think I even lasted the two days, I think I only went in the one day. No, I did go in two days, because it was the second day that I left. Also because I felt morally what they were doing was horrible.

Any other strange jobs?
Oh, you know, the standard production assistant, waiting tables, coffee runner, that kind of stuff. You can’t undercut how long you do that for. You do it for five or six years just to get your foot in the door.

Most people do that and it doesn’t amount to much.
I think that depends on what your definition is for that stuff anyways, especially now. I know a lot of people who do their own digital stuff, whether it’s a YouTube channel or [something] instead of going to film school. Waiting tables, and then every weekend working on digital shorts and things like that, which is pretty huge.

Can you imagine doing that?
We didn’t have the technology when I was in college. I think it’s an incredible opportunity. The first time I remember hearing about it was the Lonely Island, with Andy Samberg, Akiva Schaffer, and Jorma Roccone. Jorma and I went to school together at UCLA, Andy went to NYU with one of my high school buddies, which randomly, we all ended up knowing each other after college, and the three of them, with a couple of other guys, we all basically had the same PA jobs and random jobs, and they were the ones that took their money and used it to buy a DV camera and make hilarious amazing videos every weekend, and started a website. I remember reading The Wall Street Journal one day and they were on the front page, and it was a conversation about the lawsuit between NBCUniversal and YouTube over copyright, because once they were on SNL, all their digital shorts became NBC’s property. I was like, “Oh, wow, this is crazy.” That these buddies of ours started this awesome hilarious website are now the forefront of basically what’s going to be case law in copyright and digital copyright law.

That’s not something you could have predicted happening.
Not at all. It was very cool to see that. That was when you had to buy a separate camera. Now you can do all of that on your phone. So the point is that I think it’s amazing, especially if you’re in high school and you have an interest in film, even if you don’t really live in a school district or have family that’s not supportive of that, you can still go online and learn filmmaking and learn how to tell a story.

Now that your years removed from the Harold and Kumar films, do you think that role is going to define your career?
Let me back up a second: when we shot that film, we shot it for no money, it tanked at the box office, and everybody likes to forget that. It did not do well, it barely lasted the two weeks that we initially had in the theater for the film. It just did poorly.

Because people didn’t want to watch stoners?
I mean, I think it’s clear that the studio did not know how to market the film. The reason I say that with confidence instead of arrogance is because the audience went on and discovered it on their own. So, the studio did a bad job of marketing Harold and Kumar go to White Castle, it didn’t do well in theaters. And then we thought that was the end of it. And then it started running on HBO, and the next thing you know, when it comes out on DVD, fans are just discovering it. There’s almost no DVD market either, but fans are discovering it on DVD, they end up buying it, giving it to their friends and the next thing you know, they’re doing it within a frequency that we end up getting a sequel and a third film. So literally, it’s just thanks to the fans that we have this franchise to begin with. So part of it, do I expect that I can walk down the street without someone saying, with a whole lot of love and a whole lot of shouting, Yo Kumar! No. That’s probably always going to be happening. But what a ridiculous and insane thing to have happen. We all thought that it was really funny, and people like our friends would really like it, but you never know until something like that comes out.

Maybe if you passed out joints before the movie…
[laughs] That it would make people forget or more likely to remember?

I was talking about enjoyment factor.
Oh, you were talking about the theatrical release. That’s an interesting idea.

Not to deviate too far from my illegal idea, but is it true that you left D.C. because of the mugging?
No, a lot of people get mugged in DC, I was one of them!

But I was told that you were mugged an abnormal amount.
Yeah, much like a lot of my DC friends, I was walking home from work one night, and I got robbed at gunpoint. But the crazy thing was the next day at work was, there were literally like forty people who also work at the White House who were like, Oh yeah that happened to me last week! Or That was me six months ago. DC is just a wildly dangerous place.

Which is strange, right?
It’s the nation’s capital, it’s a wildly dangerous place.

Let’s backtrack to how you landed in D.C.
It’s not as weird as it sounds. In 2007, there was a writer’s strike in LA, and I was working on a show called House at the time, and we couldn’t shoot very much because we ran out of scripts, the writers were on strike, so we had to shut down production. Right around the same time, probably about October 2007, was when the lead up to the Iowa caucuses before the 2008 election was really getting going.

For a frame of reference, were you always been politically inclined?
Not really, I’ve always been interested in current events. I’ve always voted, I’m an independent, I’m still not a Democrat or Republican.

So what happened in 2007?
I’d read his [Obama’s] books, and I liked what he had to say, and had the chance to meet him and see him at a fundraiser in LA that a friend of mine was running. So I didn’t have to, you know, donate, I could just stand in the back and see how it went. I thought he was pretty legit. So I went to Iowa, which is the first state to have their vote in the primary process, and I was just going to do two days there, to volunteer and help out. But I loved it so much that I basically moved to Des Moines for the next two and half months until the Iowa caucuses, working on youth organizing and the youth vote. So after he wins Iowa against all odds – a lot of people forget that this was when, initially that summer, the president was down 30 or 40 points in the polls compared to Senator Clinton, and so everybody thought, Well, he gives good speeches and he’s an interesting, but he’s never going to win, so why bother?

It’s hard to remember that now.
Which is why I kind of bring it up, because everybody brings it up, Oh my gosh, how did you end up working at the White House? I think it’s easy to forget that at that time there were only a couple hundred people working for that campaign, and they were really smart, really dedicated people. And as that campaign picked up speed, those people who started initially, had more and more responsibilities. Since that was when I kind of started working for him, it’s not as crazy as it sounds. Then we’re on the campaign, he does a TV debate that goes very well, and then we added more staff members. People who were there earliest are trusted the most

So you were trusted?
Well, there were a lot of people there who were. There were other people there who were taking a leave of absence from like pediatrics or from being an economist or from being a law partner, and working for the campaign..

Why did you end up leaving?
So the President wins Iowa caucus and I have a chance to go to 26 other states for him on behalf of the campaign, in that next year and half or so, and then there was an opportunity to serve in the White House. I said, “Okay, I’ll do it for a year, because I’d love to take a sabbatical from acting. Serve my country, work in public service, I believe in him, obviously.” So why not go and do that? After the first year when it was time for me to leave, I realized, government works much more slowly that campaigns, or the private sector, so all of the things I was working on, only one or two of them had gotten done. And once that second year and a lot of the things I was working on were finished, I transitioned back. The sabbatical was over. It was time to go back into film. So, I still help out from time to time, not obviously as a full time staffer. But the plan was always to come back to storytelling.

There needs to be a movie made on that week like a couple months ago where—
Yeah, the health care decision and the marriage decision.

And it’s not just the things that he can do through executive authority or through partnership with Congress, it’s also the things that he can impact. The marriage equality decision, things like community college, college affordability, a lot of which happens on a state level and with state legislators, to go in and meet with people like that. Republicans on the state level are pretty inclined to meet with him on an issue like college affordability, and the concept that Community College should be free in America is something he believes in. Nothing is free, right? But what that term means is, isn’t a good idea that we as a country should allocate tax dollars to pay for universal education. Like, I think it’s a good idea. But it also happens to be three and a half percent part the cost of the Iraq war. So I think that’s a smart investment, instead of spending 97 times that.

That statistic is not going to work for some people.
For some people it won’t, but I think that’s why it’s impressive that he’s still willing to tackle these things.

So, any love for Trump?
I think he’s an incredible candidate. He’s not my preferred candidate but I enjoy watching him.

Does the popularity of his idiocy frighten you?
So I think whether he wins or not is yet to be seen, but I think the thing regardless of whether he wins or not, is that he has built or is continuing to build a certain kind of vocal popular support that I think the Republican nominee will ultimately have to contend with. Let’s say Donald Trump does not become the Republican nominee: are those Trump supporters then automatically going to support the Republican nominee or not? And if Trump is not the nominee, whoever the Republican nominee is is going to have to reach out to Trump voters and Trump supporters and get them on board, and I think that’ll be an interesting thing to watch. Because it’s a vocal chunk of the Republican party that they need – whoever the Democratic nominee is also to be seen obviously, but whoever that is, and however that plays out, are they going to be successful?

I’m curious, what do you want out of your career at this point?
I would love to be able to continue to have the privilege of being a storyteller through film and television, I love the idea that things don’t have to be mutually exclusive in your life, that there’s a time in your life where you get to have fun and be silly and stupid, and there’s a time to be serious and do serious things in life. And I love that you can do both in life, and I would love to continue to have that privilege.

Do you find it’s difficult to balance?
I don’t think so but again, there’s no handbook, there’s no handbook for even the type of work that you do in the film industry, even what with you do. If you wanted stability you should be a lawyer or a doctor or work in construction or work in something that has a little more rigidity. I don’t know but I think you’re always going to take a risk, but it’s something that you want to do, it’s always that path that’s fulfilling. I would love to be able to do both, I had the privilege of teaching college a couple of times, I really enjoyed that.

What was that like?
Awesome, I loved it! My first love is always filmmaking and storytelling through fiction, so that’s awesome. So having to do a couple other of things, that’s awesome. I just shot a documentary for VICE that’s coming out in the next week or two.

What’s the documentary about?
It’s about whether Mississippi should change their state flag. I was shooting a movie in Jackson anyways and lived there for about a month and a half, and I’d been friends with some of the VICE guys for a while, and they were trying to find ideas for a piece, and I was like, It’s interesting, living in New York or even in California, whenever you think of this issue, you think of people yelling and screaming at each other about what’s right and what’s wrong. But that’s not really the case at all; Mississippi, it’s changed a lot since whatever we think of it. There’s a huge aerospace industry, huge agriculture industry, obviously, people are really friendly and warm and willing to tell you how they feel, unlike a lot of times, you talk to New Yorkers and you know, not to badmouth where I live, it’s just a very different place than from what a lot of us think of. Confederate flag there.

You have a theory as to why people New York behave that way?
I think the misperception is that New Yorkers are rude. We’re not rude. I think the reason that somebody doesn’t smile at you when you’re walking down the street is that they’re trying to respect the concept of shared space. So people live on top of each other in New York, in a way that you don’t really in other cities. Everybody takes public transit, and so you’ve got multimillionaires standing next to people living on an hourly wage on the subway in New York. And sometimes people talk to each other, often times people talk to each other, but if sometimes they don’t, it’s because everyone’s trying to get a little bit of personal space in a city where we’re all packed in. I think it’s actually a politeness. If you actually stop to ask somebody for directions or something like that, you’ll have a really nice conversation with someone.

What about the city keeps you there?
I really like that it’s the center of a lot. I know nothing about the financial system, but it’s the center of the global financial system. There are huge histories of a lot of American immigrant communities that are there. There’s a lot of art and culture. I think the best museum in the world is the Metropolitan Museum of Art. It’s incredible, I’ve been going there since I was a little kid. I have a lot of family in New York and the New York area. And just in terms of theater, and literature, and film, the fact that all of that is packed into such a finite area is magical to me.

Sam Fragoso is a writer and editor whose work has appeared in The Atlantic, Vanity Fair, WIRED, Grantland, and elsewhere. He’s also the founder of Movie Mezzanine. A book of his interviews with emerging filmmakers, titled Talk Easy, will be published by The Critical Press in 2016.