Former Obama administration speechwriter/screenwriter/comedian Jon Lovett brings his popular Lovett Or Leave It podcast to the Merriam Theater on Sunday for a live taping, with local guests Franchesca Ramsey and Dylan Marron on the panel and actor Ezra Miller’s band Sons of an Illustrious Father on hand to play the theme song. We got Lovett on the phone earlier this week to talk about happier times in Obama White House, coping with the darkness of Trump, rookie mistakes in Hollywood, how you explain to your parents that upon graduating college with a math degree you plan to become a stand-up comedian.
PHAWKER: You graduated from Williams College in 2004 with a degree in math. Your senior thesis was Rotating Linkages in a Normed Plane. As someone who barely got past Algebra, could you sort of break that down for me in twenty-five words or less roughly what that means?
JON LOVETT: Sure, basically it’s about how things behave when the length of an object changes based on the direction it’s 
pointing. So an example would be like if you were navigating the streets of Manhattan, it’s a grid. So if you want to go a mile north, you go a mile north. If you want to go a mile east, you go a mile east. If you want to go a mile northeast, you have to zigzag your way there so you have to travel a bit more to get there. So it’s about how when things behave differently depending on the direction you’re pointing has an effect on the geometry of shapes.
PHAWKER: So upon graduation you promptly applied a mathematics degree to the only logical profession which would be stand-up. How do you explain this to you parents?
JON LOVETT: We had a bargain, an unspoken bargain, which was I was temping as a paralegal during the day and going to open mics at night, but I was also applying to law school.
PHAWKER: But then you became an Obama White House speechwriter because, according to online reports, you won some kind of contest? Can you explain that? Did they just pick your name out of a hat?
JON LOVETT: No, so here’s what it was. They solicited a lot of different people and they submitted writing samples and resumes and from that group they picked a bunch of people to write a test speech. Then they kind of read them anonymously so they could just compare based on the work. Mine was one of those anonymous speeches they picked from that group.
PHAWKER: What was your best day in the White House and worst day in the White House?
JON LOVETT: You know I would say the best day was definitely around the passage of healthcare. That was such a hard fight, it was something everybody so thoroughly believed in, there were so many twists and turns to it happening, from the death of Ted Kennedy and the election of Scott Brown to the way the bill moved through the Senate and the House, and then it finally culminated in passage of a bill that people had been fighting for, for I don’t think it’s an exaggeration to say a century. So that was the most exciting and best experience and some of the moments I most remember from being a speechwriter were speeches around healthcare. Standing in the room when he signed that bill and also being on the trail when he was making the case for it. Worst day, I don’t know I’d have to think about it. I feel a little bit removed from the true—you know look, the president deals with incredibly heart-wrenching and difficult situations around foreign policy, around life and death, around natural disasters, around murders and mass shootings. So I don’t know if it would be—I don’t know what you would point to and be this was the worst day. I remember there were some pretty dark days around the BP oil spill where there was a sense of like, why isn’t the president fixing this? And it’s like well, he’s not at the bottom of the ocean. There were lots of moments, you know, the first few years of the Obama administration, when I was there, were defined by overlapping crises.
PHAWKER: Yeah, exactly. Moving forward, lessons learned from your tenure in Hollywood doing 1600 Penn and working on HBO’s The Newsroom. If you had to do over, you would do it differently. Sorry these questions are so vague.
JON LOVETT: I would say for 1600 Penn, one thing that I learned from that experience is there’s a real similarity between speechwriting and screenwriting in that a lot of it is not just about writing, a lot of it is about figuring out how to maintain your creative and your voice and vision as you’re pursuing something. And I think one thing that I learned through the process with 1600 Penn was, I think that was a really funny show but I’d never worked in TV before, I’d never written a TV script before, I’d never been on a set before so there was so many things I was doing for the first time and I think one thing you learn in that process is what matters and what doesn’t, where should you fight and where should you let things go. I think I just have a different perspective on that now. I really liked 1600 Penn but I was a much more adept TV writer at the end of that experience than I was at the beginning.
PHAWKER: Explain the premise of Lovett or Leave It…
JON LOVETT: Lovett or Leave It is this panel show, we talk about the week’s news, we make fun of cable news, we make fun of whatever crazy stuff has happened that week. We do it in front of a live audience and then we rant about topics that have been bothering us and it’s a fun way to get a week’s worth of news that can often be pretty dispiriting in a more entertaining way.
PHAWKER: Speaking as an Obama administration alumnus, how do you cope with the Trump presidency?
JON LOVETT: Look, I read the news every day, I feel like I’m in this privileged position that we started this company because we wanted to talk about politics the way we actually talk and we wanted to engage people, wanted to help people figure out how to get involved and make a difference and that’s partly why we do these live shows, we get people involved. I also just think at a certain point, there will be dinners where I’ll be like, we’re not going to talk about politics because I’m all set today, we talked about it a lot today and I don’t need to talk about it anymore. I think its about not losing sight of the fact that what’s happening is wrong and what’s happening in our politics is dangerous and we have to fight it, while at the same time not losing sight of the fact that you can’t lose yourself in it and you can’t forget about all the other good and important things in life because we’re in this for a long fight. We’re in a fight against a really terrible group of people, some of whom earnestly believe in the project Trump has set about implementing, some who are cynically exploiting Trump because they’re ambitious, or they want to make money or they have an ideological agenda, but this combination of fools and zealots and craven people are doing real damage to this country and it’s heartbreaking. Heartbreaking to see how many people have capitulated, heartbreaking to see the racism in and misogyny given quarter by the Republican party but even as we go through this collective crises, we can’t be exhausted by it because that’s what they want. If we give up, if we get too disheartened, if we get too cynical, we’ll lose. That’s partly why we do these shows, why we do Lovett or Leave It is because it’s okay to take a break and its okay to laugh a little about the things that are so depraved and awful.
PHAWKER: Last question: Knowing what we know to date, what is your theory as to what the Mueller investigation will reveal when all is said and done?
JON LOVETT: So I’m not going to speculate about that because we’re out of the prediction business — a lesson learned the hard way in 2016. But I will say, that I am interested. Donald Trump is a cynical liar and bullshit artist who maintains no coherent worldview whatsoever. However, he is consistent on a few things. One of them is racism and misogyny. One of them is being anti-trade and anti-immigration. And the other is being extraordinarily solicitous and deferential to Russia. That defies explanation based on what we currently know, but not based on what we could learn from Mueller. I have no idea. What has been clear for the past year is that Mueller knows more than us and he knows it well ahead of us. What we have tended to learn are small pieces of information that Mueller has had from us. So I have absolutely no idea, they run a tight ship, what we know has come out of the Mueller investigation has not come from Mueller himself or his team but through witnesses who have spoken to the grand jury, through Trump lawyers, through others who have had access to the investigation one way or another. I am most interested in understanding Donald Trump’s finances. I think the Washington Post and New York Times have begun elucidating that with the steady flow of cash from Donald Trump into businesses around the world to the strange kind of scheming operation of his lawyer Michael Cohen. So I think we don’t fully know but that to me is what I want to understand more of, Donald Trump’s finances, how it works and what connection it has to Trump’s strange deference to Russia.
LOVETT OR LEAVE IT LIVE TAPING @ MERRIAM THEATER MAY 20TH 7:30 PM