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Insecure’s Leonard Robinson Wants to Show You Taurean’s Softer Side

Photo: Frazer Harrison/FilmMagic

Warning: spoilers ahead for “Tired, Okay?!,” episode six of season five of Insecure.

Sparks are flying, okay?! This week, Insecure fully leaned into Molly’s reinvention, a season-long arc that’s seen her addressing her past actions (and reactions) with her family, friendships, and romantic life. Now, that new mind-set is extending to Molly’s work sphere, where she’s often played hardball and butted heads with her co-workers.

At the work retreat at the center of “Tired, Okay?!,” things soften between Molly and her nemesis Taurean — first, when Molly lets loose at the company off-site drinks, and later when the two of them bond over their families. When her mom finally wakes up after her stroke, Molly finds herself falling into the last pair of arms she ever expected: those of Taurean, played by Leonard Robinson, who has been a reliable scene partner for Yvonne Orji since his introduction in the series’ third season. Vulture caught up with him to talk about how he prepared for Taurean’s romantic reemergence, workplace relationships, and swag-bag mugs.

Taurean has been in and out of scenes and story arcs for the past few seasons. Did you have an inkling that you may get a bigger arc before the series wrapped up?
When I signed on in season three, there really wasn’t a guaranteed episode count, so I was taking it episode by episode. It was a complete surprise for me, the amount of involvement that I’ve had as it unfolded. But you know, the show is really about the friendship between the women. Any time a man shows up on screen, you really can’t expect much.

How early during development and production of the fifth season did you find out about Taurean’s romantic arc? What was your reaction to it?
I was pretty shocked. I did not necessarily see it going where it’s headed, even with just that little scene where they’re tipping that something might be happening. To be honest, I was kind of happy being the antagonist in the office, but at the same time I joked with the producers and Issa, like, “Thank you for letting me smile this season.” In all of season three, I don’t think I smiled once.

I was going to say, Taurean has always been the antagonist in Molly’s life. What do you think makes him a realistic romantic interest for her? 
There’s a great scene in the episode where they’re talking and getting real, and Molly comes clean and admits that she’s been dealing with some things at home. Taurean says, “I also had a problem when my brother was dealing with cancer.” That really justifies why and pays off why there’s all that tension and why Taurean hasn’t really been very personable. He was dealing with personal things and doing the best that he could do, but that kind of affects your personality. I think that revelation, and being personal with a co-worker opens that up. You start to see people in a different light. You realize, Oh, I made all this stuff up. All this stuff that I thought was personal or targeted was all in my head. It really had nothing to do with me.

How did you approach crafting this character, especially now that we start to see more of Taurean’s personality in this episode? 
Knowing what I know in this episode really helped inform everything else because it allowed me to show a different side of Taurean’s personality. Taking into account that he acknowledges that he has some strong family issues that really affected his personality in the office, it felt like, Okay, if I remove that stress, who is this person? If I remove that stress and allow Taurean to enjoy himself and enjoy what’s happening, what does that look like for this man? And it’s kind of a big relief — now we can just have some fun. As businesslike and shark-like as Taurean is — and Molly too — when they clock out, they have a great time, so I just imagined Taurean on his best day without the stress.

It’s easy to attribute their connection to Molly’s personal arc this season: She’s finally actually friends with her co-workers instead of being combative at work, which everyone jokes about at the retreat in this episode. But since we haven’t seen as much of your character, do you think Taurean’s mind-set has also changed, and contributed to the budding relationship between them?
Yeah, 100 percent. I think Taurean is relieved that people can now start to see him a little more, and be open to him and the full spectrum of his personality. That also allows him to give other people the benefit of the doubt and be more open and understanding. He’s allowing more people in.

Also, if you backtrack a bit to season four, Taurean confronted Molly about how she behaves in the office. Taurean doesn’t need her to be his friend, he just needs her to be professional at work, and then she comes clean about how she wasn’t really proud about everything she did in season three. Then Taurean walks out and you don’t really know where that relationship is gonna go in the office. So when we pick up in season five, we see that they processed that and they’ve been allowed to grow and let bygones be bygones. That opens the door to potentially what’s next.

Did the writers give you any backstory on Taurean’s dating history or past? 
No. There were little clues here and there in some other seasons, like in season three where Taurean is going out of town or he gets dressed up and is going out. They hint at things, but basically Taurean is kind of a mystery.

How did you fill in those blanks for yourself? Did you make up a backstory for him?
I imagine that Taurean is the kind of guy who works long hours, is very competitive at work, and doesn’t really have a lot of time for dating. So when he does, he was probably very efficacious with that — probably a lot of surface-level relationships up until this point. I don’t think he saw a personal life as a priority, probably because he needed to find someone who aligns more with his values and career goals and personal goals.

Taurean’s big win in the episode is that he’s there for Molly while she’s going through a serious family crisis. How did you and Yvonne Orji prepare for the episode? 
The funny thing about this episode is that this was my first week of work coming out of the pandemic. So I’d like to say there was a lot of prep time, but really there wasn’t a whole lot of opportunity for us to connect beforehand. But Yvonne is a great actress and at this point she definitely knows exactly who Molly is and what she’s gonna do. Coming in off of two seasons myself I was pretty sure I understood Taurean and what’s going on. I think that’s what is also exciting about this episode: All of our reactions are happening in real time. It’s her first time saying it, it’s her first time doing it, so I think it feels a little spontaneous.

Natasha Rothwell directed this episode. Was there anything she said that guided your performance, especially in that last scene at Molly’s hotel door?
Natasha was the kind of director I needed for my first time back on set. She was very kind and very patient. I think one of the notes she kept giving me, which I enjoyed, was “just keep smiling.” Even if it’s just in my eyes, just keep smiling. It helped me out because, again, coming out of the pandemic, it was easy to think about the darkness and things going on in the world … but she just kept reminding me to lighten up and enjoy myself.

My favorite one-liner in the episode was your deadpan delivery of “my mom had a mug.” Are those written in or did you improvise on set?
That was a real fun run. Natasha is a great improviser and has a great background in improv, as do I — I’ve spent many, many years doing improv and I’m a main company member at the Groundlings Theater. So we just went on a run and let the camera roll. There’s probably about 20 different alts just for that little scene.

What would you put in your swag-bag mug?
I think we said water, pens, soup or chowder or gumbo, or really anything liquid. You could use it as a doorstop, you could put it on your desk just to remember …

Getting involved with a co-worker is messy territory. Do you think that poses any hurdles for Molly and Taurean’s future?
It definitely is a precarious situation to be dating somebody you work with. I think that’s also why the end of that scene catches Taurean off guard. He walks in with no intentions, just making sure she has a swag bag, and because of the timing and the emotional state that Molly’s in at the time, they share that awkward moment. That being said, that does not necessarily mean it’s day one of a relationship. But I think it opens up some possibilities. Even though it is messy, I also think sometimes in these jobs where you work so much, that’s the only opportunity you’re gonna get. It can also be a benefit when you work in high-pressure situations or very intense long hours — you do get to know somebody.

Are we fools if we get our hopes up about Taurean and Molly ending up together?
First of all, I’m just surprised and really loving that there are people who are have their hopes up, period, about a Taurean and Molly relationship, because I never saw it going down like that. But the finale comes out at Christmas, so maybe some people will get what they wish for and maybe some people will get some coal.

What can you tell us about the remaining four episodes of the season (and series)?
One thing I really love about this season in particular are the time jumps and the different fantasies. They’re really playing with different forms and mixing it up, and every episode is so fresh and engaging. Even after watching all this time, you can’t expect or predict anything.

This interview has been edited and condensed for clarity.

Insecure’s Leonard Robinson on Showing Taurean’s Softer Side