Tristen J. Winger Talks So Help Me Todd & The Impact of Insecure

From Insecure to his current hit, So Help Me Todd, Tristen J. Winger is making his mark on Hollywood with a warm presence that shines through whenever he’s on-screen. Tristen’s career continues to ascend, and we’re all lucky to witness it.

We got a chance to jump on a call with Tristen and chat with him about his scene-stealing role as Lyle on the CBS legal dramedy, his time on Insecure, and what kind of advice he has for those interested in acting.

Tristen is as charming as charming can be and an absolute delight to talk to. He was candid and kind, and you’re really going to enjoy this lovely conversation. So dig in, and check it out!

I wanted to start talking to you about So Help Me Todd. First of all, congratulations on the full-season episode order.

Thank you.

That’s exciting.

Very exciting.

How pleased have you been with the reception of the series and the way audiences are reacting to it?

From the beginning, when we shot the pilot, as we were shooting it, I’m thinking to myself, and I’m saying to my castmates, “You guys, this is going to go. We’re going to do great. I think we’re going to exceed everybody’s expectations, including our own.”

That’s exactly what we’ve done.

I didn’t have an idea of what numbers we would do, but once the numbers started coming out, week after week, we’ve been growing and consistent with our numbers and with our demographic. It’s exciting to see that so many people are responding to it.

I’ve got friends messaging me. My mom tunes in every week. She relates to Margaret’s character so much. The response has been overwhelming. I’m really grateful that we’re here.

What is it that you think is connecting with audiences? I think, from my perspective, it’s very funny. I find myself laughing out loud a lot. But they also have these fascinating cases and these exciting dynamics too. Would you agree that audiences are connecting with that piece of it?

Yeah, absolutely. It’s a one-hour drama, but we’ve got bits of comedy every page, every minute of this show, which is so fun because when we look at other drama series, yes, they’re very dramatic. We look at other procedurals, it’s very dramatic, and there’s so much going on. It’s gut-wrenching.

It’s nice to have something that’s a little bit lighter, like our show. I feel like our fans are connecting to that. Also, they’re connecting to the relationship between Margaret and Todd. I’m sure we either have that relationship with our parents, or we know someone with that relationship with their parents.

I kind of have that relationship with my mom. Because our moms, our parents, they just want to love us. They just want us not to have to fail or face any issues in our lives. That’s what we see in Margaret. I think that everybody can relate to that.

Mm-hmm, oh yeah, for sure. I actually watched the pilot with my mom. I was like, “Could you imagine if I had to work for you?”

Uh-huh, exactly. My mom just retired as an elementary school teacher last year. She was a teacher for 30 years. There were some summers when she would be in the classroom, and I wouldn’t have school because I’d be off for summer.

I’d go to her classroom and help her with whatever she needed in class, along with her teacher’s assistant.

It’s kind of that same dynamic where it’s like she’s telling me what to do. Of course, this is a classroom. She’s got a classroom with fourth and fifth graders, so of course, I’ve got to do everything that she says.

But I can’t imagine being an adult and doing that. I can’t imagine being my mom’s teacher’s assistant. I couldn’t imagine doing that, especially when I’m like, “But I think we should do things this way. I know what I’m doing. I’m a professional in what I’m doing. You can’t tell me what to do because this is my job, what I’m doing right here.”

I can’t imagine having that relationship with my mom. So for Todd to have to do that, as a private investigator, working for his mom at a law firm ...no, thank you. It’s very entertaining to watch, though.

What attracted you specifically to the role of Lyle?

With Lyle, as soon as I read the sides for him, and I saw that they described him as someone that was difficult and fastidious, I immediately jumped to, “Okay. I know what this is.” I thought about my previous experience working in retail and dealing with my coworkers.

I’m an affable person. I’m very likable. I get along with everybody. But there are some people who just rub you the wrong way. I imagine if I was a person who is super type A, and I had this guy who’s now just bursting into my office, and I’m supposed to work with this guy? He doesn’t follow any rules.

He operates in a gray area all the time. I can’t even think of the word right now, but he’s just off the wall. And I’m a person who follows the rules. He’s by the book, and I don’t like people touching my stuff, and he’s doing everything I hate. I can relate to that.

Because even when I think about my younger brother, my brother is four years younger than me, and I’m the clean one. I’m the clean brother. We live in a house together. I keep everything clean. I can tell when he’s been in the kitchen because all the cabinets are open, and the milk carton is set out.

The milk carton that was supposed to be in the fridge is still sitting on the counter. Drawers are open. There’s food on the counter from when he made a peanut butter and jelly sandwich. I know what that relationship is.

Except this version of it on this show is a lot different, of course, because they’re not blood brothers. But you can see how their relationship is like two brothers who don’t hang out with each other because they are just different people.

So once I figured all that out, I’m like, “Okay. This is going to be fun to play.” Lyle is someone who’s very type A. He’s very dry. He’s sarcastic. He’s also funny in his own way. That’s a lot of fun to play, for me.

He’s hilarious. That whole conversation in So Help Me Todd Season 1 Episode 4 about Marvel, Wakanda, and all that stuff, was hilarious.

Yeah. That was a lot of fun. It’s in that moment where you realize, “These guys are the same person. These guys are both nerds. They like the same stuff. They just have different points of view on this.”

It reminds me of me and my best friend from high school. We’re still friends to this day, a 20-plus-year relationship. The new Black Panther trailer came out. We were talking about that. We were talking about Harrison Ford playing a character in the Marvel Universe. That reminds me of me and my conversation with my friend.

So, I’m like, I know what this relationship is exactly.

To this point, I don’t know how far along you guys are in filming, but what has been the best part about filming the series so far?

The best part is any time a majority of the cast gets to come together to play in a scene. I just love being around everybody. I’m trying to think. We haven’t had a scene that we’re all in together yet.

So when we get together to do table reads, and we get to just play off each other, then that chemistry of everyone is so much fun for me.

I don’t know if you know this, but I enjoy having friends. I enjoy just being around people. So the more I get to spend time with these people, the more fun I have, and the more we get to play.

I went to Amazing Grace Conservatory when I was in high school. That was run by Wendy Raquel Robinson. We put on theater productions. We had to rehearse several times a week leading up to our show dates, our premiere dates.

That was just some of the most fun I’ve ever had, just being around all these other creatives and people who like to play and joke around and sing and dance. This reminds me of that. This is almost like a drama camp almost, in a way. Any time I get to act with these folks, I’m having a great time.

It’s funny. You mentioned that episode, that conversation between Todd and Lyle about Marvel. That is one of my favorite scenes so far. It is so ridiculous. You can see that Lyle is so passionate, and he has all the knowledge. You know he spends his time on internet forums arguing with people.

Lyle is that guy. When you go to a webpage, and you’re reading an article, and you see the comment section, and you see some people going back and forth, that’s who Lyle is. He is in the comment section. He is a comment section comment warrior. That’s who Lyle is.

That’s a great description. That’s actually a great description.

You went into my next question, which was this cast is stacked, starting from the top with Marcia Gay Harden, and you’ve got Skylar and Madeline and everyone. You touched on this, but I was going to ask you, do you have any fun behind-the-scenes stories from your time filming thus far?

Or just some fun things you’ve gotten to do with the cast?

Yeah. There’ve been a couple of things. I remember one of the first weekends that everybody came down. Excuse me. Came up, came over, whatever. Came over to Vancouver. One of our recurring cast members, he plays Allison’s husband, Chuck. He has a boat. He invited us to go on a boat on a lake and just roll out with him.

We were on that boat for five, six hours. We were out there eating snacks and having a good time. That was a blast. We jumped in the water. It was very cold. I decided to get out and get back in the boat. That was a fun time.

What weekend was it? It wasn’t the 4th of July weekend. But a couple of weeks after that me, Inga and Rosa went up to Whistler in Canada. That’s a mountain town, so it’s a smaller town. We went to this spa where we had to be quiet. No one could talk. You couldn’t have your cell phones out.

This was a hydrotherapy spa, so you got the hot pool for 20 minutes, then you get out of the hot pool and jump straight into the ice-cold bath, and you’re in there for 20 seconds. Then you go relax, and you lay on a hammock, or you go in the solarium, or you go in the steam room, or you go in the sauna. We did that for six hours.

I fell asleep in the hammock in the rain. I didn’t care. I was comfortable.

Again, any time we just get to spend with one another, doing whatever we like together, is a good time.

Most recently, the Canadian Thanksgiving was a few weeks ago. We all got together and had a little potluck, where we just brought some of our favorite dishes over. We went over to Maddie’s house and just hung out, ate some food, and drank some wine.

Switching gears a little bit, I have to ask about Insecure and what it was like. Insecure is iconic and revolutionary. What was it like being on a series of that magnitude for the past few years?

First of all, Insecure was a whole blessing because it introduced the world to Issa, one of my friends from high school. By way of introducing her, it also introduced me to the world.

That was such a magical show because we had never seen anything like it before. We had never seen anything like it before. It was on HBO. We came from YouTube. We were doing a series on YouTube, and then she got her HBO show. It was magical from end to end, first of all, because we hadn’t seen a show like that before.

Also, because of all of the conversations surrounding the subject matter of each episode, from talking about sexuality, men’s sexuality, and talking about, “Well, this woman cheated on this man. Was she wrong? Was she right? Well, this guy wasn’t doing anything. He was sitting on a couch.”

Then at the end, spoiler alert, she stayed with him after having a kid with someone else. All those conversations we wouldn’t have had if this show hadn’t existed. All the engagement that we had with the fans.

Then, of course, just playing this character, Thug Yoda, aka Miles, who on the surface has gang affiliations, but really he is a loving father who’s just trying to figure it out. That’s who he is. I saw on the page, “Yeah. That’s funny. He changes the C words to B words. Hilarious.”

But also, who is he? As a man, he is a father who loves his daughter very much.

We saw that in the finale. He’s out front of The Dunes, taking pictures of his daughter because that’s what she wanted to do, which is also meta because if you’re ever in Englewood and you drive by The Dunes, you will always see somebody in front of that apartment taking photos, because of the impact of that show.

It was magic. I’m so happy and so grateful that I got to be part of that magic.

Yeah. Oh yeah, for sure. If you could see me, I’m just nodding along to you because I feel you perfectly summed up the show so well.

Man, oh, man.

If you could craft the perfect role for yourself like you got the script, and you’re like, “This is my dream role,” what would that look like for you?

Lyle is very close to that. What I would add to Lyle...I love that he gets to be sarcastic. I love that he doesn’t hold back and doesn’t feel he has to answer to anyone.

I would also add because this is something that I haven’t really seen before in movies or television, I love a good spy movie. I love a 007. I love an action flick. It’s great.

I’m just like, it’ll be so dope if Lyle was actually just this badass who went on missions secretly and didn’t tell anyone because he had this secret life and this secret identity where he would just mess stuff up. Not in a bad way, but he would get into some stuff because he’s got to travel to Europe.

He’s got to travel to wherever. He’s got to go to Australia. He’s got to do some Mission Impossible type stuff.

That’s the dream role. The dream role is basically a black Tom Cruise doing all of these missions. It’s a Mission Impossible, a Top Gun: Maverick, all balled into one.

Okay. Now would you do your own stunts, like Tom Cruise?

It’s a discussion. We can have that discussion. We can visit it on the day. I will do as much as I can, as much as my body can handle. I will go over it with the stunt coordinator. He will show me some things. I will either say yay or nay. But first things first. We got to protect the money, and the money is Tristen, so we’ll see.

But here’s the thing. Here’s the thing, though. I do love adventure. I went kayaking. A couple of weeks ago, I went jet skiing with some of the cast from Fire Country. I went skydiving a couple of years ago with my good friend Novi, Novi Brown, who’s on Sistas.

So I do love adventurous stuff. I just want to make sure I’m safe and not going to get hurt. That’s all.

Are there other aspects of filmmaking that you’re interested in, stepping behind the camera, writing, or anything like that?

Absolutely. I love, love, love music videos. There are still some great music video directors out there. Calmatic has directed a bunch of videos, and he directed some new films coming out. His first film coming out is the new House Party. He’s got White Man Can’t Jump coming out. Calmatic is one of my favorite music video directors.

Dave Meyers is one of my favorite music video directors, but also Melina Matsoukas, who directed We Found Love, and also transitioned to television and film with Insecure.

I believe that these music video directors transitioning to traditional film and television are bringing something new to that landscape. When All Def Digital started their YouTube channel, me and my best friend and one of my other best friend’s brother got to collaborate and do these parody music videos for their YouTube channel.

I would write up the treatments for them for the videos and also produce the music for them for those parodies as well. So eventually, I’d love to get to that point where I can start directing television and film and also writing for television and film.

I was reading your bio and saw that you originally planned to get into the medical field and then ended up in the arts. It’s similar to me because I have a biology degree, but I didn’t want to pursue it, so I went a different route.

Mm-hmm.

Do you have any advice for people interested in breaking into acting, but maybe it’s not something they always wanted to do, or they’re unsure of themselves?

My thing is, try it. Because even with mechanical engineering, I tried. I went to Cal State Northridge. I was there for three years. I just did not love it, but I thought it was what I had to do because it was something that my mom and other family members were like, “You need to get a job. Engineering is it. This is the next big thing.”

I was like, “Okay. It’s the next big thing. I want to be a big thing. Let me go into engineering.” But I didn’t love it.

Math every day? Math every day? I’m good at math. I love science. But every day? No, thank you. No, ma’am. No. I do not want to do that. But I tried. I tried it. It just didn’t work out.

I also tried music production, audio engineering. I was doing really well at that. But then, at the school I was at, it was just getting too expensive for me, so that didn’t work out.

But acting and performing, and being an entertainer, is something that has always worked for me since I was young. I was always performing in a school play or going and taking classes somewhere. Then there was meeting Issa in high school, doing Awkward Black Girl, and finding success there.

It just snowballed into where I am today. I’ve always found success doing this.

To anyone who wants to try out acting, go for it. Try it out. If you love it, great. Stick with it. If you’re doing it just because it’s like, “You know what? I want to be famous, but I don’t love this,” it might not be for you. Do whatever calls you. Do whatever you love. You deserve to experience whatever it is that you love.

You deserve to experience that. So, try it out.

I hope somebody hears that because I would’ve loved to hear that. I was the same way. I thought that’s what I had to do. Looking back, I wish I had gone a different path. But you get where you’re meant to be in the end, I think.

I agree. You get to where you need to be, where you’re supposed to be.

I have one more question for you here. I work for TV Fanatic. So I wanted to know from you what shows you are currently enjoying and if you have any go-to shows that you have seen over and over again. When you need just a comfort show, what would that be?

Oh, absolutely. My comfort show, easy, is Insecure. That’s my comfort show. Specifically season four, episode eight. The date that Lawrence and Issa had, where they rekindled, is my favorite episode of television ever. Ever. Love that. Love that episode.

As far as television I am obsessed with, that I fan out over today, my favorite television show on the air is Atlanta. I love Donald Glover. I love Atlanta so much. If I created a TV show, it would look and feel like Atlanta. That is my bar right there.

The other show, if we’re going network, besides our show, of course, if we’re going network, I’m loving Abbott Elementary. I love Abbott Elementary so much.

One of the main reasons is because my mom is a teacher. All of these deep-cut references they have on that show, I’m like, I know all of this stuff because my mom talks about this stuff all the time.

But besides that, even if I didn’t know anything about the education system and elementary schools, it is hilarious. The jokes are nonstop. Principal Ava is hilarious. What? Sheryl Lee Ralph is killing it. Everybody is bringing their A+ game to that show. I love it. I love it.

So yeah. Atlanta and Abbott Elementary, those are my shows. Then if we want to do one more, Raising Kanan. Oh my God. Raising Kanan. Yeah. Those are my shows. I ride hard for those shows.

That’s a great list.

Thank you so much for your time today, Tristen. This was a lot of fun -- continued success with the series.

Thank you so much. I had such a good time talking to you. Thank you.

You can watch So Help Me Todd on Thursdays at 9/8c on CBS.

***This interview has been edited for length and clarity.***

Whitney Evans is a senior staff writer for TV Fanatic. She is a lover of all things TV. Follow her on X.