'Awards Chatter' Podcast — Jill Soloway ('Transparent' & 'I Love Dick')

The force behind two of TV's edgiest shows and the winner of the last two comedy direction Emmys opens up about the bumpy climb from writer to showrunner, a career-changing gamble that paid off, gender, sexuality and trying to "topple the patriarchy" on screen and off.
John Parra/Getty Images
Jill Soloway

"I think of myself as a bisexual non-binary person," says Jill Soloway, the primary force behind two funny, smart and edgy comedy series currently streaming on Amazon, Transparent and I Love Dick, and the winner of the last two best director of a comedy series Emmys for Transparent, as we sit down in the living room of Soloway's home in Silver Lake to record an episode of The Hollywood Reporter's 'Awards Chatter' podcast. Soloway, who is 51 and has two sons through relationships with men, now prefers to be described with gender-neutral pronouns (they/them/their). "It helps me understand that none of those old labels actually really worked, whether it's 'straight' or 'gay.' For me, the biggest real categorization is 'trans' instead of 'cis.'"

Until recently, Soloway felt personally conflicted about gender and sexuality. When Soloway's father came out as trans in 2011, that not only inspired the creation of Transparent, but also caused some introspection. Soloway explains, "I was like, 'This is my legacy. I have a genetic legacy. If my parent is trans — if my parent's relationship to their gender has always felt fraught — this is maybe why my relationship to my gender has always felt fraught.'" Adds the writer-director, "All of that stuff, I think, created a stew of confusion for me that ended up feeling, day to day, like rage, dread, anger. I still have some anger, but I just feel a little relieved of all of those things."

(Click above to listen to this episode or here to access all of our 150+ episodes via iTunes. Past guests include Oprah Winfrey, Steven Spielberg, Meryl Streep, Eddie Murphy, Lady Gaga, Robert De Niro, Amy Schumer, Will Smith, Jennifer Lopez, Louis C.K., Emma Stone, Harvey Weinstein, Natalie Portman, Jerry Seinfeld, Jane Fonda, Lin-Manuel Miranda, Nicole Kidman, Aziz Ansari, Taraji P. Henson, J.J. Abrams, Helen Mirren, Justin Timberlake, Brie Larson, Ryan Reynolds, Alicia Vikander, Warren Beatty, Jessica Chastain, Samuel L. Jackson, Kate Winslet, Sting, Isabelle Huppert, Tyler Perry, Sally Field, Michael Moore, Lily Collins, Denzel Washington, Mandy Moore, Ricky Gervais, Kristen Stewart, James Corden, Sarah Silverman, Michael B. Jordan, Kate Beckinsale, Bill Maher, Lily Tomlin, Rami Malek, Allison Janney, Trevor Noah, Olivia Wilde, Eddie Redmayne, Claire Foy and Andy Cohen.)

Soloway was born and raised in Chicago and was a creative and curious person from a young age, but explains, "I had been learning about feminism, and I didn't really understand how to square it with popular culture." In a college application to the University of Wisconsin at Madison, Soloway expressed a desire "to be a translator between some sort of complex ideas and mainstream media," which is precisely what Soloway has done through television. But first, Soloway embarked on a career in advertising, not realizing that a career in TV even was possible because "I didn't see any women in that role so it just didn't occur to me to be those people." Involvement with the production of TV ads, however, led to greater exploration, starting with a gig as a production assistant for Chicago-based Kartemquin Films on projects including the landmark 1994 documentary Hoop Dreams. Also in Chicago, Soloway became involved with the Annoyance Theatre, a group that creates original plays through improvisation, which motivated Soloway and sibling Faith Soloway to create a stage production about the TV show with which they were most obsessed as kids, The Brady Bunch, which proved a phenomenon. It brought the two, who were in their mid-twenties, first to New York, where they were signed by CAA agents, and then to Los Angeles, where Soloway decided to settle and pursue a career as a TV writer. "It was a dream come true," Soloway says.

Over the ensuing years, Soloway climbed the TV food chain in various writers rooms, starting as a staff writer (The Steve Harvey Show), then graduating to story editor (Nikki) and eventually becoming a co-producer (Six Feet Under), with occasionally side-employment as a hand-holder, of sorts, for shows made by newcomers to TV (e.g. How to Make It in America, Looking and United States of Tara). "It's very easy for me to be creative," Soloway says. "In fact, it's harder for me not to be creative. I have so many ideas that I'm always trying to not think of new things, which is a strange feeling." Soloway "dreamed of having my own show," but just couldn't make it happen. "This was pre-Lena Dunham, pre-Mindy Kaling, pre-Tina Fey, pre-Broad City," Soloway notes. "People did not like weird girls, they did not like gross girls, they did not like strange women. I was still writing the same stuff I'm writing now. I've always been the same person." Then, a perfect storm struck: At a moment when Soloway was between jobs, the national recession and a writers guild strike hit roughly simultaneously. Soloway's savings got depleted, past-due taxes mounted and another job proved impossible to land. "I was pretty desperate, financially," Soloway recalls. "I was going around to all of the people who had shows and kind of begging for jobs. I remember begging for one on Two Broke Girls." Then a promise of salvation came through with an offer to work on Glee — but it just as suddenly evaporated, apparently because Soloway had a reputation for being being difficult to work with. "I literally just started sobbing, I was so upset," recalls Soloway.

In a roundabout way, though, it was the best thing that ever happened to Soloway. A loan of $25,000 from a sympathetic agent was used to make a short film, with the hope that a successful short might lead to a feature directing opportunity. "I said, 'I have to double-down on me,'" Soloway recalls, and it was a gamble that paid off. The short, Una Hora Por Favor, got into the Sundance Film Festival, where Soloway began "feeling like a director for the first time" and set to work on the feature script, which became Afternoon Delight. The feature ultimately was made with financing and a talented character actress, Kathryn Hahn, thanks to chance encounters at the Silver Lake farmers market, and it not only played at Sundance a year after the short, but brought Soloway the fest's best director prize, as well. It later would serve as a prototype for the show that would become Transparent, which, like I Love Dick, also stars Hahn, as well as Kevin Bacon. But Transparent probably never would have happened at all if Soloway's father hadn't called from Chicago and come out as trans. "It was a pretty overwhelming moment," Soloway recalls, while admitting, "There was a part of me, even during that phone call, where I knew I was gonna write a TV show about it."

Soloway created Transparent, a dramedy about an Los Angeles-area family that is rocked when the seventysomething person long-known to the adult children as their father comes out as transgender, and pitched it all over town, but "nobody wanted it," at least among the usual suspects — HBO, Showtime, FX, IFC and the like. But then Amazon stepped forward, agreeing to permit Soloway to make a pilot and retain ownership of the footage if the show was not ordered to series, a highly unusual arrangement that was important to Soloway, who figured the footage could be turned into a film if Amazon passed. Amazon, however, embraced Soloway's vision and gave Transparent a green light, so the writer-director began staffing up — primarily with writers and directors who hadn't worked much in TV, many from the LGBTQ community, and all with the goal of making a show unlike any other on television. The show's first two seasons created widespread buzz and conversation — what Soloway calls an "unbelievably delightful awakening of the power of television when it comes to politics" — and it received best comedy series Emmy nominations, star Jeffrey Tambor won for best actor in a comedy series Emmys and Soloway's direction also was recognized; in addition to writing and directing many of the show's episodes, Soloway also serves as its executive producer, with Andrea Sperling. Transparent's third season dropped last September and is Emmy-eligible now.

Meanwhile, right after Transparent's third season was completed, Amazon made it known that it had an opening in its schedule, so Soloway and Sarah Gubbins pitched I Love Dick, a show about a female experimental filmmaker who becomes infatuated with the male artist sponsoring her husband's research fellowship. "We wanted to explore whether there is such a thing as 'the female gaze' and we wanted to make sure we paid homage to all the women who had been attempting to have their voices heard over the years and hadn't really had the chance to," says Soloway, who is an executive producer of the show, with Gubbins and others, and who also directed the first and fifth episodes of its first season, which dropped May 12. (All of its writers and all but one of its directors are female or gender non-conforming.) Episode five, "A Short History of Weird Girls," has garnered especially widespread acclaim, with New York Times TV critic Alexis Soloski calling it "whip smart, radical, keen and poignant," as well as "the best 20 minutes of television I’ve seen in years." Soloway says of that particular episode, "I was pushing myself beyond what I had already figured out as a director and attempting some new techniques to see how far I could push myself."