You may be familiar with Jena Friedman as the host of the smart, darkly comedic yet thought-provoking TV series, "Indefensible" and "Soft Focus."
Or perhaps you're familiar with her work as a standup with her special, "Ladykiller" or her work with "The Daily Show."
Now Friedman is turning her attention to a new outlet with the essay collection "Not Funny: Essays on Life, Comedy, Culture, Et Cetera." Pivoting from joke writing to non-fiction is a whole other beast, she told WPR's "BETA."
"I think writing essays, especially when they are earnest, there's a vulnerability to it and I think that exposes you a little bit more," she said. "Whereas like with a joke, you can hide behind it. But if you're writing an essay about something, you're exposing yourself in a way that I'm not totally used to."
Friedman also admitted that essay writing, or perhaps getting started on essay writing, is her biggest hurdle.
"I think a lot of comedians and performers, you kind of become a performer because it's easier to do that than sit down and write," she said. "It's my Achilles heel. It feels like pulling teeth to sit down and write a first draft."
Fans of Friedman's trademarked edgy, sometimes offensive but always sharp satirical style will find lots to enjoy here, as even the origin story of the title is layered.
"I got into comedy by writing an academic paper about comedy, which was very not funny," Friedman said. "I just think the term 'not funny' is so funny to me because it's so subjective and random, and I just thought it would be a really fun title for the book."
The title also turns the tables on the backlash she's received to her satirical tweets that some feel went too far and dubbed "not funny." Plus, there's also a practical reason for it, Friedman said.
"If you're not a fan of my comedy, and you Google my name and 'not funny,' a link to the book will come up," she quipped.
A standout essay is one titled "An American Girl's Story." It was inspired by backlash that the Middleton-based doll company American Girl faced in 2005. By then, American Girl had been sold to Mattel and the fictious backstory they created for their doll Marisol Luna disparaged an actual Chicago-area working class Mexican neighborhood.
"It was funny that there was so much controversy around this doll company, but also the company itself, just how tone-deaf they were. It just was perfect comedic fodder to make fun of them," Friedman said.
Friedman, who was writing political sketches for a small Chicago theater company at the time, constructed a concept and extended sketch of a satirical doll company called "Refugee Girl." The bit was similar to the famous Garbage Pail Kids satirical swipe at the Cabbage Patch Kids doll line.
"It was like this overly earnest company that had all these refugees from all over the world. And I wrote a play and I got all my friends in Chicago to trust me, to perform in my play. And we put it up. And the whole experience was wild," Friedman said.
Each week, Friedman would perform in a series of sketches, each as a new doll in the "Refugee Girl" line. She would provide her own hilarious, satirical and equally tone-deaf backstory to dolls like "Fallujah Jones," an Iraq war refugee settling on the west side of Chicago to teach little kids about "Western neo-imperialism from the safety and comfort of her pink-and-white Laura Ashley bedroom."
Friedman's ability to offer up sharp social criticism effectively is on display in the essay "Brief Interviews with Hilarious Men." The title itself is a play on David Foster Wallace's famous short story collection, "Brief Interviews with Hideous Men."
In the essay, Friedman interviews several of her fellow comedians like Bob Odenkirk, Fred Armisen and her old Daily Show boss, Jon Stewart, and gender swaps the inane questions she and her fellow female comics have faced for years.
"I remember seeing a video of Merrill Markoe in around 1980 and the interviewer said, 'Do you think women can be pretty and funny?'" she said.
Friedman herself recounts receiving similar questions as recently as 10 years ago.
"It has gotten better, but we still get questions that I think when you're interviewing someone, if you can sit back and say 'Would I ask a guy the same question,' and if the answer is no, then you know, that's a lame question," Friedman said.
Even the experiment wasn't on equal ground, though, Friedman explained, because some of the comedians were aware of her premise. She did find a fascinating discovery that some comedians — like Jim Gaffigan and Patton Oswalt who were on tour and answered the questions in writing — had far different takes.
"It was so great that they answered the questions, but it was just funny because so much about comedy is context and tone," she said. "When you read them, they're so off-putting, but when you're actually having the conversation with someone and even like my tone or my inflection and something kind of mitigated any harshness in any of the questions."
Friedman extends this conceit past gender, to race.
"I think that artists want to be perceived for the work that they do, not their identity for the most part," she said. "Identity always factors into it. But I remember seeing someone recently emailed me and asked me to weigh in on like Jewish humor, and I just was kind of put off by that."
"I'm definitely Jewish, but my humor isn't necessarily about being Jewish," she continued. "When you talk to anyone, think about just the types of questions that you're asking and why."
Friedman said the toughest essay to write in "Not Funny" was one about cancel culture. She feels the discussion about it is so "tedious and exhausting" and struggled to find a unique approach.
"I did kind of come up with my shtick, which is really just that conversations about cancel culture themselves are kind of a grift and like, I want in on it too," she said.
Friedman plays off of her own experience with a short-lived tenure as a writer for the TV show "Roseanne," which was canceled after creator and comedian, Roseanne Barr, posted a series of incendiary tweets in 2018.
"It did get me thinking," she said. "I was able to incorporate my experience working for Roseanne, that brief half day where I was writing on her show before she got canceled, and just weigh in on other things that I actually have experienced firsthand connected to cancel culture."
"Not Funny" is available from Simon and Schuster.