This Week in Comedy Podcasts: Jessica Williams on ‘Fresh Air’

The comedy podcast universe is ever expanding, not unlike the universe universe. We’re here to make it a bit smaller, a bit more manageable. There are a lot of great shows and each has a lot of great episodes, so we want to highlight the exceptional, the noteworthy. Each week our crack team of podcast enthusiasts and specialists and especially enthusiastic people will pick their favorites. We hope to have your ears permanently plugged with the best in aural comedy.

Fresh Air - Jessica Williams

Leigh: Not only did we get a bonus episode of 2 Dope Queens this week, but Jessica Williams is also the guest on this week’s Fresh Air. She’s there to talk with Terry Gross, or “Ter Ter” as she so affectionately calls her, about her new movie The Incredible Jessica James, which is out on Netflix this Friday. In the movie, which was written for Williams, Jessica James is a playwright who has a wall covered in rejection letters, something Terry Gross (as much as I want to, I don’t think I can pull off calling her Ter Ter) assumes Jessica Williams must not know anything about, having been hired by The Daily Show when she was when she was only 22 and still in college. But she quickly sets Terry Gross straight, explaining “I am a 6-foot-tall black woman and I have been since I was about 13” – she’s seen her fair share of rejection. They also cover what it was like growing up religious and even being part of a purity ceremony as a kid to now being so open and speaking so candidly about sex and relationships on stage. I hope this conversation comes full circle and Terry Gross is a guest on 2 Dope Queens. [Apple Podcasts]

How Was Your Week - A Bell Tolling

Noah: Loyal patience paid off this week for those who kept How Was Your Week inactive in their podcast feeds when Julie Klausner dropped the first episode in almost a full year. The 45-minute monologue flies by as Julie waxes on whether David Lynch is just for goyim (“He’s what my dreams look like,” her friends tell her), how her cat, Jimmy Jazz, asserted his dominance so fiercely when she tried to find him a friend that she was forced to return Mr. Yams to the animal shelter, and recounts the shouting match she had on the phone with a German hotel clerk who insisted that she couldn’t afford Julie a refund because that was not old, dried blood on the pillowcase, Miss Klause-nair, but your blood. She thinks you hit your head. She’s worried about you. You should probably see a doctor. Without a guest and without any indication that she’ll be back next week – or this year, even – Julie isn’t exactly bringing the band back together, but it’s nice to hear from her anyway. [Apple Podcasts]

Off Book: The Improvised Musical - Shrugging Destiny w/Paul F. Tompkins

Marc: I don’t know how you feel about musicals, but I’m generally not a fan. Nonetheless, there’s something about folks like Jessica McKenna and Zach Reino having the stones to bang out a crazy, tuneful show in less than an hour, all made up from scratch, that is pretty damn funny. Especially when, for their premiere episode, they enlist the improvisational skills of podcasting’s hardest working guest, Paul F. Tompkins. Up front, Paul F. cops to the fact that musical make ‘em ups isn’t his strong suit: “After I come up with one rhyming line, I feel I’m pretty much done, even though the song keeps going.” Springboarding off a short discussion about how generally disappointed their parents were at the outset of all three of the players’ show business careers, Tompkins does an admirable job keeping up with the breakneck clip of “Shrugging Destiny,” one boy’s (later man’s) tragedy-strewn struggle to find singing success. With tunes like “Be Yourself First,” “No One Wants to Eat at Chipotle,” and “Dang, Dang, Dang,” Off Book might not be coming to Broadway any time soon, but it bodes well for the episodes that follow. [Apple Podcasts]

The Longest Shortest Time - Casey Wilson and Jessi Klein

Kathryn: Guest host (and former guest) Casey Wilson steps in for Hillary Frank this week and chats with Inside Amy Schumer writer Jessi Klein. First, if you haven’t read Klein’s memoir You’ll Grow Out of It, you must. Go do that. Then listen to this episode as a neat supplement to her essays on marriage, fertility, and epidurals. Wilson and Klein have known each other for a long time, but not always as close friends: Casey first encountered Jessi many years ago in the UCB scene as the ex-girlfriend of her then-boyfriend, a “tall improv gentleman” who remains nameless. Casey felt insanely jealous. But they both got over that guy, got successful and famous, married other guys, and now their two-year-old sons Max and Asher are best friends. Amazing that they could navigate that kind of nuanced relationship arc with more self-awareness and poise (and better jokes) than most comedians, while we’re still deciding if women are as funny as men?! So brave. Wilson’s self-deprecating cheer and Klein’s deadpan honesty make for delightful conversation plus a voyeuristic peek into the friendship circles of women with kids in Hollywood. [Apple Podcasts]

Don’t Ever Change - Dave Stone

Pablo: After taking a month off to honeymoon, John Roy is back with another episode of his high school podcast Don’t Ever Change. This week, comedian Dave Stone helps us understand what it was like to be raised in northern Georgia in the early ‘90s. Stone was a comedy nerd-slash-jock who loved Seinfeld as much as he enjoyed playing linebacker for a team that went defeated (not a typo for undefeated) during his entire tenure. But the most fascinating chunk of the podcast is where Stone analyzes the segregated place he grew up in and the proudly conservative people he left behind. Stone recalls not meeting a black person until he was a teen and that this led to an embarrassing moment of subconscious racism when he and a black friend ogled the hottest white girl in their school. Even if he didn’t purse comedy, it doesn’t sound like Stone would’ve stayed given that many of his schoolmates were so stuck in their ways, they never even drove an hour away to visit Atlanta. Don’t Ever Change remains as one of the better podcasts available for good reason: It has a simple premise that, if you’re a podcast host, makes you want to kick yourself for not thinking of it first. [Apple Podcasts]

WTF - Randy Newman

Marc: People that have been humming and tapping their feet to the tunes of Randy Newman that he’s created for Pixar and Disney movies (he’s done 23 soundtracks in his day) may not have any idea of the breadth and depth of this artist’s pretty amazing career that spans more than 40 years. A baker’s dozen worth of solo albums in addition to the movie music has helped him rack up half a dozen Grammys, a pair of Oscars, and induction into the Rock n’ Roll Hall of Fame. And he’s still going strong. The impending release of his new album Dark Matter prompts his visit to Marc Maron’s garage and it’s a very engaging WTF conversation. Maron seems a little baffled that Newman isn’t churning out tunes 24/7 or that the muse isn’t forcing him to pour music from his head constantly, but the musician insists he’s simply not driven like that. Another interesting revelation is that Newman doesn’t play that well with others. Not as a matter of choice but, as he tells his host, he mostly composes and plays on his own, so when he is in a situation where he’s at a performance or recording session with other musicians, he has trouble keeping time and staying on the beat. He busts another myth I thought was true that the characters in his songs are not really even remotely autobiographical in nature. While some tunes reflect his feelings, he’s not picturing himself as the hero in anything he writes. He’s definitely been an influence on other songwriters and singers over the years, and it’s great to hear him spin his story here. [Apple Podcasts]

Other Podcasts We’re Listening To:

Maltin on Movies - Jenny Slate

With Special Guest Lauren Lapkus - Erin Whitehead, Stephanie Allynne, Mary Holland: Sex and the City

The Roundtable of Gentlemen - A Goose Needs a Maid

Regretsville - A Very Potter Regret (with Mike Kelton)

My Dad Wrote A Porno - “Yorkshire”

Hollywood Handbook - Hollywood Masterclass: Everybody’s Gotta Eat! (w/ Hayes Davenport)

The Best Show - Special Friday Night Show! Bad Roads! More Oreo Talk!

Got a podcast recommendation? Drop us a line at

Pablo Goldstein is a writer from Los Angeles, CA.

Leigh Cesiro is a writer living in Brooklyn who only needs 10 minutes to solve any Law & Order: SVU episode.

Marc Hershon is host of Succotash, The Comedy Soundcast Soundcast and author of I Hate People!

Noah Jacobs is a writer, podcaster, and mark who lives in Minneapolis, Minnesota.

Kathryn Doyle is a science writer from New York.

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