Insecure is just two episodes into Season 5 when L.A. Confidential sits down to chat with Leonard Robinson, who plays attorney Taurean Jackson, co-worker of Issa Dee’s (Issa Rae) best friend, Molly Carter (Yvonne Orji). Given we’re so early into the final season of the beloved HBO show, Robinson can only get so detailed about what’s in store, but he does note one big change for his character.
“I joke with the showrunner and Issa— it’s like, thank you for letting me smile this season because I feel like in Season 3 I smiled one time when [Molly] showed up at the office and after that it was downhill,” he says.
The perpetual poker face of Taurean isn’t exactly the standard for Robinson. In a show last month at The Groundlings Theatre (aptly titled “A Groundling on Elm Street), Robinson’s knack for inciting abundant laughter is made clear during a sketch in which he and scene partner Matt Cook are teaching a comedy class. Stifled chuckles came from both the audience and their fellow company members performing in the sketch.
“We’re also cranking our cast members while we’re on stage, which is fun because they don’t know what they’re going to read [for the ‘class’ material,]” Robinson says.
In addition to his role on Insecure and being a main company member at The Groundlings Theatre, Robinson’s TV credits include Life of Crime, NCIS, Young Sheldon and Adam Ruins Everything. And before hitting the silver screen, the Howard University alum appeared in a number of shows at The Williamstown Theatre Festival, New York Fringe Festival and Studio Theatre in Washington D.C.
Robinson’s foray into performing ultimately began as a kid while watching Sesame Street.
“Somehow it clicked for me that I… was watching actors and that I could be on TV,” he explains. “I was like, ‘I want to be the kid playing with the Muppets. How do we do that?’ And I’ve been on a chase ever since.”
Committed to sports throughout his adolescence, Robinson finally took a formal acting class as a Howard student. He always knew he wanted to be an actor, but had to find a round-about way into the craft.
“I tried to enroll and figure out a way to audition for Howard’s school of drama, but my parents were like, ‘We're not paying for that. I don’t know what you’re thinking.’ And so when I got to Howard, I was trying to figure out a way to sneak into the School of Fine Arts.”
Post-graduation, Robinson was set on his plan to work for a couple of years to save enough money to then quit his job and pursue an acting career. He lasted two years as a tech consultant doing backend web programming.
“The hours were ridiculous. I was working like 14, 16-hour days,” Robinson reflects. “I realized this isn’t the life for me. I’m putting 14, 16-hour days working to build these websites for these companies that I don’t care about and I’m tired. I’m exhausted. I was like, ‘What if I just did that for myself? What if I spent 16 hours a day trying to figure out how to be an actor?’”
Knowing he had some friends in the local acting scene, Robinson made the jump to New York City.
“It was a relief but it was also terrifying,” he says. “I remember standing in the middle of Times Square in the heart of Broadway just thinking, ‘How?’”
After gaining his footing in New York’s theater and stand up worlds, Robinson made the jump from New York to Los Angeles during the mid-aughts. He made the realization one winter that there were only so many plays where young Black men could be cast versus the abundance of TV roles available out west.
“It was like the combination of a freezing New York winter and me just watching TV and paying attention,” Robinson says. “[There were] maybe eight television shows in New York primetime, versus like 80 in L.A. That was just me doing the math.”
His first show ended up being MTV’s improv game show, Wild ‘n Out. A newcomer performing in front of a live studio audience alongside the likes of Katt Williams, Robinson says the experience was intense.
“I think the thing that I figured out on that show in my four seasons was that I just have to be me, just lean into the uniqueness that is me,” he says. “That’s what made me more successful.”
It’s partly how he landed the role of Taurean. In an essay for Backstage, the actor opened up about how he auditioned for a number of roles on Insecure before landing the part.
“Looking back, I don’t know how well I would have played those other roles,” he wrote. “What I do know is that Issae Rae and our showrunner, Prentice Penny, believed that I was the only one who could play Taurean.”
Robinson hints we have more to see of his attorney character in the final leg of Season 5. Fan predictions have been floating around the internet for a while about Molly ending up with Taurean, but Robinson seems fairly flabbergasted at such rumors.
Still, he acknowledges his key role in Molly’s emotional journey. In Season 4 Episode 2, she apologizes for burning him on a past project. It’s hard to tell how sorry Molly really is in the moment, but it’s definitely a stepping stone toward her realizing she’s not always right. Ultimately, through the resolution of a professional conflict, Taurean facilitated the opening up of Molly’s personal conflicts.
“I'm honored and just feel real fortunate to be part of that universe,” Robinson says of the show. He acknowledges the importance of Insecure bringing representation of Los Angeles’ Black community to television and particularly points out the due credit to Rae, Penny and pilot director Melina Matsoukas for also employing people of color behind the camera and investing in their careers.
“I think that's why [Issa] became so huge, he says. “It's not just about when you get an opportunity, trying to get all that you can for yourself. They made sure they were also trying to get opportunities for other people.”
Photography by: Shela Shiloni