Boston Calling Comedy Report Day 1: Jon Lovett Brings Silliness and Meaningful Insight

In day 1 of Boston Calling’s comedy offerings, we learned that we have Harvard University’s admissions department to thank for Lovett or Leave It and Pod Save America co-host Jon Lovett’s chipped shoulder. “You can buy your way into it! It’s part of it! It’s been part of it for almost 400 years!”

The Crooked Media co-founder has done just fine since the school just outside of Boston (and host of the Boston Calling Festival) turned him down, and will be spending two nights at the festival as part of its comedy offerings. Friday, he hosted a live edition of Lovett or Leave It to a crowd of about 800, even as the sun shone and music blared outside.

Lovett was joined by activist and writer Blair Imani, Daily Beast contributor Erin Ryan, and former White House deputy chief of staff Alyssa Mastromonaco. Together, the quartet spent ninety minutes bantering about current events and the political climate in recurring segments like “What a Week,” “OK, Stop,” and the rapid-fire “Rant Wheel.” Through it all, Lovett and his panel brought about a means to engage in political thought that Boston Calling booker Trevor Solomon was excited to bring to the annual festivities. “I think it’s important to embrace it, and to have people who speak about it,” he said about featuring Lovett or Leave It and Pod Save America on the lineup.

As important: that those conversations be funny. Imani, Mastromonaco, and Ryan, despite less comedic background, did manage to tinge conversations about cancelled North Korean summits (Mastromonaco, a former Obama staffer alongside Lovett had to matter-of-factly ask, “Lots of smart people had tried this before. How did he think this was going to work?”), a proposed domestic gag rule (in which Lovett asked the profound question, “isn’t every sex toy, in a sense, educational?”) and an extended conversation about the fidelity of the Millennium Falcon’s fidelity as the fastest ship in the universe (I won’t ruin it, but Imani’s proposed answer makes sense). These silly asides, shared alongside meaningful insight into current events, was welcome…and yet gave me mixed feelings as a longtime festival attendee.

The laughs that Lovett and his panel offer are undoubtedly more cerebral and more niche than any this portion of the festival has seen before. What’s more, to start the offerings in the arena with a political podcast (which strikes an unequivocally liberal tone) is a move that sends a message. This means of opening the festival’s comedy offers a stark contrast to previous years’ prominent featuring of local talent, and I’d be remiss if I didn’t say I missed the feeling they brought to the arena. While we may see a return to the locally-tinged lineup in coming years, I will also admit that this shift in programming does serve an important purpose.

In closing the podcast, Lovett shared an impassioned reminder with the crowd in the arena of their power as primary elections continue to take place ahead of this year’s crucial midterms. “We’re in the final stretch now, the election is coming, and everything we do now counts. We have to give it everything we have.” To ensure that the ideals Lovett and Crooked Media do translate from thought to action, the team has partnered with for its “Pod Tours America” travels. According to their Field Director Kim Selig, the goal is to make sure that listeners left not just informed and passionate, but also active. And how does comedy help that goal?

“It helps bring people together over something common,” Selig shared with me ahead of the recording. In her eyes, people who can connect over finding similar things funny or interesting can bridge gaps in perspective and experiences, leading to a kind of understanding. Their hope: that people first and foremost register to vote, but also engage in information campaigns and help people rally around issues they care about. Like Crooked Media, is a nonpartisan initiative- their goal is that whatever side people take, they feel empowered to act in support of their beliefs.

In ending the podcast (with the regular segment “Ending On a High Note,” Lovett shared a bit of hope. “We’ve seen countless women and men and others, and our job now is to harness this incredibly energy” to enact our beliefs and needs as a country in forthcoming elections. Lovett or Leave It served a similar role for the festival lineup, bringing an energy and excitement that likely will carry through to the arena’s remaining offerings.

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Amma Marfo

Amma Marfo is a writer, speaker, and podcaster based in Boston, MA. Her writing has appeared in Femsplain, The Good Men Project, Pacific Standard, and Talking Points Memo. Chances are good that as you're reading this, she's somewhere laughing.


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