Texting and Talking with Judah Friedlander about If the Raindrops United

Judah Friedlander photo by Yoko Haraoka
Judah Friedlander
photo by Yoko Haraoka

Most of the time, setting up a celebrity interview (whether to promote a TV show, movie, book, whatever) results in an extended series of emails between publication and publicist; it is very rare for the subject at hand to become directly involved. And so it was with no small amount of surprise that—after emailing back and forth with a representative from Hachette, the publishing company behind comedian Judah Friedlander’s new book If the Raindrops United—I received a text reading:

Hi. Its Judah. I think ur interviewing me and want to come to a show of mine. Let me know the details. Thx

The surprise came not because the text was unwelcome—in fact, it’s much easier to set up a meeting with someone directly, rather than through a third party, no matter how helpful that third party is—but because it is so, so rare for any well-known person (let alone someone who was featured for seven seasons on one of the most acclaimed television shows ever, as Friedlander was in 30 Rock) to actually deal with the minutiae of promoting him- or herself. But within minutes of meeting Friedlander (a day after a flurry of helpful, friendly texts), it was easy to see that the comedian is something of a rare breed: open, warm, helpful, and generous with his time in the service of promoting a project about which he feels strongly. 

If you only know Friedlander from his portrayal of Frank on 30 Rock (which, get acquainted with his other acting work stat; he was revelatory—and unrecognizable—in American Splendor), you might think that he’s as disaffected in real life as he was on the show. But actually, the similarities between Friedlander and Frank pretty much begin and end with the novelty baseball caps they both wear. (On the night of our interview, Friedlander wore one with “World Champion” spelled out in sign language.) Instead, Friedlander deals with issues like gentrification and classism in both his stand-up act and in If the Raindrops United.

After watching Friedlander perform at the Village Underground’s branch of the Comedy Cellar to a sold-out show last Thursday night, we walked around the corner to talk about his book at a table in the Olive Tree Cafe, the restaurant over the original branch of the Comedy Cellar, where Friedlander would also perform that night to another sold-out crowd. The two-minute long walk resulted in several people gawking in recognition of Friedlander, who was incredibly nice when stopped by a Canadian tourist who was a huge fan of 30 Rock; the walk also resulted in me having a newfound awareness of just how popular stand-up comedy is right now, as I overheard one couple making plans to give the Comedy Cellar’s bouncer a fake name “like, a really common one” in the hopes of getting in to the 10 o’clock show that night.

Friedlander, who has been performing at the Comedy Cellar “since at least 93,” confirms that, while the neighborhood has obviously changed, and “there’s not many live music places around here anymore,” it’s still “really good for comedy… and [the Comedy Cellar] is doing better business than ever.” Which is easy enough to understand after watching a set of Friedlander’s; he’s so natural onstage, engaging with the audience as the baseball-capped embodiment of the George Saunders quote about humor, namely that it’s “what happens when we’re told the truth quicker and more directly than we’re used to.”

This is what Friedlander excels at: nimbly revealing the blunt truth of everything from American exceptionalism to the woes of a gentrifying city before a laughing audience can slowly—and then all at once—grasps what it is exactly that they’re hearing. Friedlander loves being on stage, telling me, “I’ve been doing it so long and I feel like it’s what I do best and it’s what I like doing. It’s actually relaxing for me…I’m more nervous now [talking to you] than I am on stage.”


It is abundantly clear that Friedlander has no interest in the type of branding or promotion that is usually encouraged for celebrities who are releasing new projects. While Friedlander is on Twitter and Instagram, he isn’t completely sold on everything that social media means when it comes to a creative career. He says, “It’s weird because when I started standup, I don’t think I’d even heard of the Internet. I hadn’t even heard of email. Just the world, the country’s become… everything’s business and marketing now. When I started it was just about jokes. It was all about how to get funnier. There was nothing about branding. I never heard of that word until five years ago. There was nothing about branding or marketing. I’d never heard of any of that stuff.”

Despite his reluctance to participate on social media from a purely branding-friendly standpoint, If the Raindrops… actually had its beginnings on Instagram. Friedlander explains to me as he flips through his phone, “This [book] started kind of on Instagram. I started about two years ago… 105 weeks ago. I started making ads for my own shows. Just about exactly two years ago. So I was touring a lot. I always carry around pen and paper, and I was traveling a lot, so to combat anxiety with downtime and traveling I started doodling, whether it was on a piece of paper or on my phone. With Instagram, I’d started doing jokes with photos, but then it became drawings. After a couple months I had about 30 or 40, and I realized that maybe I had a new book here.”

The result of this realization, If the Raindrops United, is by turns hilarious and challenging, simple and chaotic, provocative and sentimental—a fascinating peek into Friedlander’s mind. The drawings and cartoons in the book deal with issues like gentrification and classism (as Friedlander says, those are “the big themes in the book” and are examples of how “everyone will get the drawings, but if you live in New York you’ll really get them”), as well as sexism and racism, environmental concerns and our reliance on technology. There’s also a lot of penis humor. Reading it straight through (which Friedlander recommends, telling me “I do think it’s better if you read it from front to back; my mind’s kind of all over the place but I did try to organize this so that it has a crescendo that builds toward the end”) feels like one long episode of hearing Friedlander expound in a stream-of-consciousness, free associative kind of way. In other words, it’s captivating and funny and seriously thought-provoking.

Friedlander agrees that the book is a total reflection of his mind and philosophies, saying, “If the book sucks it’s not because of anyone else. It’s because of me.” Which for some people might be extra anxiety-inducing, but for Friedlander, is actually as relaxing as doing stand-up because it means he’s in control, and he’ll succeed or fail on his own terms. There are images in the book that he fought for (including one that I love of what can only be described as breast-birds flying over a setting sun; Friedlander says about it, “Almost everyone hated that one. And I’m like I like it! I fought for it.”) and it’s clear what a passion project this is for him, and how happy he is to be sharing it.

We stop talking eventually because it’s time for him to go back on stage. The World Champion hugs me goodbye and heads off to take the stage in front of a sold-out crowd, some of whom probably lied their way inside. And I head to the subway to re-read If the Raindrops… and spend a little more time in the brain of Judah Friedlander.

Judah Friedlander will be at PowerHouse on 10/21 at 7pm to promote If the Raindrops United
PowerHouse Books: 37 Main Street, DUMBO


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