Journalist. Playwright. Podcaster. King of gay Twitter. Thirty-four-year-old Ira Madison III sports many hats amassed over a brief but brilliant career in media and the arts. They fit atop another he’s had since birth: Milwaukeean.
Madison is perhaps best known now as one of the hosts of “Keep It,” a podcast that riffs on the relationship between pop culture and politics. He credits the restraint in covering breaking news as part of the show’s success, along with the obvious chemistry and incisive wit shared by its trio of hosts.
While “Keep It” is Madison’s most visible role, it’s not his only active creative space. A lifelong comics fan, he helped adapt a Black Panther saga for a forthcoming audio drama. He also wrote for the now-ended Netflix series “Daybreak,” and the soon-to-debut Netflix series “Q-Force,” an animated LGBTQ spy spoof starring Sean Hayes. He and friend Julian Breece sold another show called “Cancelled” to Warner Bros. and are now developing the pilot. And earlier in his career he worked for Buzzfeed, GQ and New York magazine.
The foundations for this in-demand, culture-shaping output were laid in Milwaukee. He and his family – led by his sheriff’s deputy mother and Army sergeant major grandmother – moved throughout the city as he grew up. He remembers living in the center of Riverwest long before the neighborhood acquired any cool bohemian vibes. Then everyone moved out to 58th and Burleigh, where Madison would walk a mile to Collector’s Edge Comics each summer Saturday for the latest issues of “Spider-Man.” Later summers were also spent working various Summerfest jobs with close friend Kori Ashley, now a Milwaukee County Circuit Court judge.
Madison attended MPS schools for elementary and middle school, then entered Marquette University High School. There he joined the student newspaper and fell in with the theater kids, awakening the interests that would bend the arc of his life. “I had a column in the Marquette Flambeau,” he says. “It almost felt like an early version of ‘Keep It.’”
Another friend created his own theater revue and enlisted Madison to script a one-act play staged in the cafeteria. It was a transformative moment for him. “That was what made me fall in love with wanting to write stories myself,” he says.
After high school, Madison’s time in Milwaukee was largely over. College called him first to Chicago, then later to New York. In between, he returned and worked at the Milwaukee Election Commission, which only cemented his view that destiny lay elsewhere.
Madison still regularly visits the city, though he has not always welcomed the journey. The open wounds of childhood – he didn’t come out as gay until moving away – and his prolonged stay at the bottom of the professional ladder made him dread the prospect of homecomings for many years. “It always felt like the Chekov play The Seagull, like I was going to a funeral every time I went home,” he says.
The distance of age and security of success has evaporated his lingering trepidations. Madison now relishes his returns and marks each one with a visit to Blackbird Bar in Bay View to sip a Wisconsin-style old fashioned.