Theo Hollingsworth on being a Multi-Hyphenate Filmmaker
By: Laísa Barros
Tags: Interview, Filmmaking, Series, Podcast

Theo looking directly at the camera. He is wearing a blue button up shirt. The background wall is slightly darker blue color than his shirt.

Laisa: Hello, everyone. Thank you for tuning in today. Today I have a director with me, and I’m really excited to be talking with him and I’m going to let him introduce himself.

Theo: Hi, I’m Theo Hollingsworth. I’m a multihyphenated filmmaker. So I’m a writer. I’m a producer. I’m a director. I’m a video editor. And I’m like I wanna be actor, I suppose, as well. I also lead a video production internship program as well, so yeah, multi, multi hyphenated, filmmaker.

Laisa: Yass! That is wonderful. So your life is all surrounded by film. Like that’s, that’s your passion. That’s what you enjoy. Not only do you make, but you also teach people how to. I wanna learn a little bit about, when was the first time that this came about for you? Like how old were you that you were like, “I’m going to be a filmmaker and I want to do all these things related to the entertainment industry”?

Theo: Yeah. So I remember growing up I mean, my, my family was big on TV and stuff, so I remember just like really, I think my first inclination that I wanted to do something like in the entertainment realm was just like watching Eddie Murphy, standup comedy, special Eddie Murphy, raw. We had that on VHS and we always used to watch it. And I just, I think I was like, really like, “Oh wow. He gets to like, make people laugh and like do that as his job.” So I definitely, I remember as a kid wanting to be a standup comedian and then like I think it got paired with film probably in like high school. There is, like a video production class. I was like, “Oh, okay, cool. Like, I can make my own videos now. Like I understand how to edit and stuff.” And so like once it wasn’t so abstract idea of making videos, I was like this is how I could get like my comedy out or my art director activity out. Yeah. And then, so those things kind of made me want to get into it. I also like ended up watching this documentary. It was really influential. I remember towards the end of high school and trying to figure out what I wanted to major in, in college, it was called Unforgivable Blackness by Ken Burns. And it’s like a multi-part documentary about the first, Black heavyweight boxer champion Jack Johnson. And I’d never heard the story and the way they told the story is really dope. And I was like, “Okay, cool. Maybe I want to go to the documentary route now that I understand editing.” And then I was like, “all right, cool. I want to go to school in film.” But yeah, that’s kinda like the things like the pivotal things. I think that like kind of led me down the path of wanting to get into, into like filmmaking.

Laisa: So it’s like, you had an example that you saw of somebody doing it and then it occurred to you that you could be doing that. So that is so cool because it’s not always that we get the influence as children so I’m so happy that, you know, you can share that with us. But I know that right now you’re working in a series that is really cool. And it’s going through many screenings throughout Oakland. Could you tell me a little bit about how long did it take you to make that series? What was the process behind it and how did your idea come about?

Sirius Lee The Problematic Time Transplant Poster

Theo: Yeah. Yeah. So the series I’m working on right now is called Sirius Lee The Problematic Time Transplant. It is a web series that I wrote, I produced and I starred in. The series is a comedic series with a like a lot of musical elements in it. And it’s about time travel so it’s about Sirius Lee, he’s a martial artist slash rapper slash quantum physicist living in Oakland in 1980. He opens a time portal and ends up in modern day Oakland 2020. So then he has to find out like he had to fight to get back to this time and like retrieve his time capsule which has got a time machine to get him back to his time period. And the idea for this came about, you know, I’ve always loved time travel and I really wanted to, like, I’ve always joked about wanting to like do the remake of back to the future and call it Black to the Future. And I remember like, I think it was spring of 2019. I saw like a movie that was being marketed as Black to the future or Black back to the future. And it even has Michael J. Fox and then the original back to the future in it, that was like, “Oh, okay, cool. It’s I guess it’s already been done,” but I think what I, what I noticed that was lacking in that movie for me was just kind of like joy and lightheartedness of the original back to the future. And so I wanted to do like a time traveler film that features Black people, but that was a little bit more lighthearted, you know what I mean? So I got into writing and I wanted to do something more lighthearted. So I was just like, you know what, I’m going to write it myself. And so I got into writing and I wanted to do, yeah, like I already had this. I liked the name Sirius Lee. Sirius is spelled S I R I U S. And like, there’s like a, like a star constellation and it like represents like God and God at times. So I was like, all right, cool. That’s a pretty cool first name. But then I was like, all right, but I want it to be like an action hero. So Lee is just kind of like that name. I feel like, you know, like Bruce Lee, you know, Bruce Lee is actually like, you know, he had a dojo I’m in the Bay area and like, did a lot in the Bay. So I was just like, alright, cool. Like this sounds like an action here. Sirius Lee. And then as an added benefit, every time you say it, if can say it like all one, like together, Sirius Lee it sounds like seriously, and that’s always fun to play with in the, in the series and stuff. So, yeah I came up with that concept and then the whole process of producing it is like, I mean, it was hard. Like I’ve done a couple of other, like I produced a pilot a while ago, you know, I’ve done like more documentary stuff. And of course I did some things in college or whatever, but this is kind of the most ambitious thing that I did. I did it in phases. And I feel like I’m pretty happy with like the, the way I went about it. I didn’t rush into it, but essentially, like the first thing I did was like, before I even wrote the script, I just came up with the concept of this time traveler rapper slash scientist from the eighties winds up in modern day. And I was like, okay, it’s a really weird concept. And I got to, I know I’m not going to have like the budget. I need to just pay a whole crew to come on board for this. It’s not exactly a project that like grant applications are like, you know, fawning over to like pay for. So I knew I was going to have to be working with folks for low budget. So what I did was I developed like a 30 second teaser for it. I just like hired like a voiceover actor online who like had like a deep voice or whatever. And then I just got a couple of my friends together and we went over to like, my homie’s like art studio and we just shot, like in a day we just shot like a really cool little quick teaser of that. And with that quick teaser, I was able to show that to people. And then. Get them onboard to help me out as directors and as production assistants and his camera operators, because I was able to just send them the video view rather than me trying to explain it like long form, they get that and be like, “Oh, okay, cool. This looks kind of silly. I think I’m down.” Once I like, yeah, I did that. And then I went back to actually writing the season. I just pretty much did that by myself. And I got like feedback from a couple of close friends. They gave me a really lot of great info and another thing that really kind of worked out because of that, it’s like, I always knew that Sirius Lee was going to be this rapper. Like I was going to be a part of his persona, but I had no plans of like writing any rap song. Like it was just going to be kind of a thing in the back. But then like I showed that teaser to this music producer and he was like, “yo, this is dope. I want to produce all the music for it.” And I was like,” Oh, okay.” And so once I wrote the script, I wrote in a song, like I wrote a little quick rap song for like every episode. And then I shared them with him and he was able to like, you know, emulate eighties, hip hop beats. And I was just like in character, just rapping it Sirius Lee. And the song came out pretty dope. From there, like, as I wrote it, it kinda just naturally organically like, Oh, it’s probably like a two, three month process, but it kind of naturally organically like develop, eight of these 10 episodes. Every episode is like really short so there’s a whole season at this point, you can watch in 38 minutes. And so each episode is like, you know, Sirius doing some crazy caper and then he learned something and then he writes, he sings a rap song basically about what he has learned or about what he’s doing in that episode, you know?

Laisa: Yeah.

Theo: Yeah! And so like, it’s fun because like we got into shooting, like, it was nice because half of it was just shooting music videos. Right. We didn’t have to do like. Just full episodes of rigid dialogue. And it was just like, alright, now hit it. Right. And there, like this episode just breaks out in the song. So yeah, I mean, that was the process. We’re writing it and developing it. I like hired a few of my friends as actors, and then I found that a really talented actor on this audition and I found a really talented actor there. I got a big bar. I got a bunch of dope location donated to me. It’s really awesome to shoot in Oakland. Oh yeah. And then I knew it was gonna, it was gonna cost like $2,000 to shoot it. And so, I was like, okay, I think I got a little bit of money saved up for this, but I was kind of sweating. I was just like, hoping people are going to be able to work for like really low, low pay, I mean, which they still did, but like low to no pay. Okay. But then at the last minute, I got a really awesome freelance gig that came up that was like, exactly what I needed to film this, or I like shot that. And it was real quick lifted out to them. And then I had the money, I needed in the bank. The shooting and I scheduled the shoot in January of 2020. It took a bit longer. I hosted a little fundraising campaign and along the way and some things. But yeah, like I shot it in over for two weekends in January of 2020, I had enough money to fly my mentor out, it was like this amazing cinematographer. He was super helpful. He came with all the equipment. I borrowed some equipment from my full-time job, which is a video production studio. I enlisted the help of a bunch of interns from my intrinsic program and help PA’s or audio technician and the camera operators. My coworkers were also involved in it, so yeah, kind of like, like there was a lot of energy around it. I mean, it went off without any major hitches. And the timing, I feel like it’s perfect. Cause like we shot it a month later we had kind of like, you know, like a very kind of rough assembly of it. And then we were getting into the editing process. and then COVID hit. And so it kind of stalled it a little bit. You know, I ended up just like, at that point, taking on a lot more editing than I wanted to. And then they got slowed down the process. But also like, I think the timing worked out well because I didn’t really have a plan with what to do with it. So I kinda needed to figure out okay like once this is done and how are people going to see it and stuff. So yeah. Now it finally worked out where like, we’re pretty much done anything yet. And while I was editing it, I was also applying to film festivals and just kind of doing research and they’re the best way to release a web series in this era. And now that it’s done in like, I got accepted to four film festivals.

Laisa: Yes, I’m snapping my fingers.

Theo: Yeah. Yeah. So, yeah, like timing really worked out. Like I didn’t, I think if I finished it earlier and applied to some festivals. It was so new. And the COVID at that time period that like a lot of film festivals were postponed or canceled indefinitely because they didn’t have enough time at that point to keep it to being a, to being virtual film festivals, but having that period of time. And then they kind of figured out what their plan of action was and get the infrastructure in place. It still have a film festival virtual. Really worked out. So like now folks know what they’re doing has some experience with it. Yeah. Instead of we’re in our theatrical the actual release of it at this point.

Laisa: Yes. I’m so excited. I know that, I’m definitely going to be in one of these festivals that is coming up for online. So I’m excited to see it. I would love to know although you already told me that you wrote, you composed, you star in this series, you were the director. So you were already doing all of this. And then when you told me that, Oh, when COVID hit, I had to do even more. And I was just like, Whoa! You know, a one man show, but it’s not, it just felt like you have done so much. And I’m just so proud of you. I’m constantly looking at your Instagram and like the posters, like who came up with the idea for the posters. I love that logo for your web series and the posters, everything coming up. And when you put the snippets of this series, I’m just like, okay, I can’t wait to see this. Cause it’s so funny. So, can you tell me a little bit about what was the idea behind? I mean, I know that it fits nicely with the theme, but who came up with those posters?

Theo: Yeah. Yeah. Okay. So it really, I think it worked out this thing. I just did things just as a safety. I didn’t know what I was going to be able to use them or whatever. So like, that was another thing that like, Before COVID I think it was like last, last year, it was like late 2019, you know, as we’re rehearsing and getting ready for the shoot, I was like, “Hey, pass, we need to, we need to make sure we know all of our costumes. Right.” We had all these costumes that were donated to us. I scheduled the day for us in tech where our costumes. And I was like, “you know what, while we’re wearing a dress, you know, fitting our costumes and stuff, let’s actually just take some photos since we’re all here in our costumes. And you know, we can use them for publicity and stuff later.” And I’m so glad I did that because it would totally back and save and do a photo shoot during COVID or anything like that. So we did that and, once I got those photos, actually, so I did have a director, my best friend, his name’s Fox Nakai and he’s like a director on it. He’s also an awesome photographer. He took all the photos. Then I had all these amazing high quality photos, and I was like, you know what? I want to make a dope poster. So we found some cool inspiration from like blaxploitation films, in classic 80 films. And then I’ve known about this really awesome designer his name. He goes by Pretty Standard. And he’s based in Oakland and I just hit him up on Instagram, got a huge Instagram following and stuff. And, you know, we kind of know each other a little bit and I hit him up and he was a down. And so I gave him all the photos. I gave him some inspirations and he just like, I love people like that. He’s like, “all right, cool. I don’t need anything else.” Right. “I’ll do four posts for you” I was like, “all right, that’s cool.” So he, I gave him all that a week later, we had the first one, you know what I mean? And, yeah, he, he did a really good job of incorporating not only the characters into the posters, but also all of these elements from Oakland, which I love for the show that it’s like really Oakland based series. And then he also, did it, he hand created the font for the logo and stuff like that, which was really, yeah, it was really neat. And so yeah, and he’s like kind of the major designer that I worked with on those posters. And then I worked with another really close friend who’s out in Detroit and he’s been able to adapt that. And helped me to create additional images. I really, I think with what I did, I was doing a lot of research. I had a lot of time at home to do research and, perfect timing was this movie called Bill & Ted’s Excellent Adventure Have you ever seen Bill & Ted’s Excellent Adventure or heard of that?

Laisa: No, I haven’t.

Theo: Okay. So, um, it’s another time-travel comedy film. There’s actually, stars Kiana Reeves. And I forget his name and it came out in the nineties. I remember watching it as a kid. I was like, these are awesome. These are hilarious. Right. And so they’ve been working on a reboot of that. So they’ve got, they brought Bill and Ted back. Right. And they just released it. I still haven’t seen it yet, but I’ve been, but I found out about it because I’ve been getting all these Instagram ads for it. So I was like, let me check out their Instagram account. And I like look at their account and I showed that to my designer, Detroit. And I was like, “yo, like, this is a time travel comedy. So clearly with a bigger budget than us, but like, let’s try to like emulate that. You know what I mean?” We already kind of had a lot of the similar color palettes and things like that. So I tried to keep that. You know, like I’m definitely not copying, but I do like the cool inspiration from a lot of areas. So I’ll definitely say Bill and Ted, like the reboot was Bill and Ted 3 that was like a huge inspiration. And I don’t know where else it will look, you know, like if that has not come up, like, cause I was like, wow, like, this is exactly what I’m trying to do. So it was really important to have consistency. We had a dope logo and I’ve been able to adapt things. I’m really looking at that.

Laisa: Yeah, no, and I definitely see the consistency and I just love how everything came together. So thank you for sharing that. That’s amazing. I was just like, wow. Well, another thing that I want to focus on is a little bit on the downside and like you as a human being. So was there ever like a challenging time during like creating this series or throughout your journey as a filmmaker that you felt like quitting or that you learned something and then you were able to, you know, continue onto this path and encourage others to do the same?

Theo: Yeah. Yeah. I mean, this is probably been the challenging time to have done a venture like this. So really, like I would say, like I told you, I started writing it last year in 2019. And like right after I kind of shot my teaser trailer and it was like really getting heavy into writing. You know, my wife woke up one morning, like, to like a frantic call from her girlfriends and found out that like her best friend took her life. and so that was like, Whoa, like she had like a year old daughter at the time. And so like, he had to like, you know, we had to go to Chicago for that funeral. And then like literally a month later, I’m getting off work, headed home and I get a frantic call from my homie. And he like, “Hey, our mutual friend from high school, he died.” And I later found out that he took his life. So that was all that wasn’t like September 2019, October 2019. And like, it’s easy, especially with a comedy. I was like, it was easy for me, just put this down, you know, it was like it just not the right time and stuff. But like, I don’t know something about it. It was like, I, you know, I keep saying, when people ask about it, it’s like I’m taking Sirius Lee, seriously. You know, I feel like it’s a way for me to address like real things that think that important issues. But in the side of like a comedian kind of like way, and also like it’s, it’s like in a way, like an honor of like this time period that we’re in, you know, my friend who has he actually worked. He lived in Detroit, but he worked like Detroit pretty easy major motion picture scene for a bit, right? Like a few years ago there was a lot of tax incentives for major motion pictures come out there. And so he was like doing special effects. He worked on like, one of the Batman movies, like all these other movies. So he was like, in that, that world, if you were, if he had not passed, he would have been involved in Sirius Lee in some capacity, you know? And it, it almost felt like it would be kind of, I mean, you know, him and I growing up, like, we always kind of ideated about like what we were going to do next. And like, art was really big, a part of we’re doing so, like, it just felt like you kind of. A wasted opportunity or kind of go against maybe what he would want me to do if I was just like, “Oh, I’m just going to put this down” so I can, you know, I just like, obviously like some, some, like, I dunno, like I think if it was also a timing thing, I was still in the writing. And so writing phase of it and it’s like, there’s so much grief. These it’s like writing for me is almost like a kind of a form of meditation. So it’s like, if it were like, all right now, like if that had happened and it was like, “no, you need to be organizing and having meetings with other people and planning the shoot and directing people.” I don’t know if I would’ve been ready for it, but like at that point I was like still in the writing phase. So I think that might’ve even expedited some of the writing for me, because it was just like, I can’t cope with other people right now. Things are hard. Let me just put on my headphones and write, you know, so. Yeah, that was hard and then honestly like this past, last, last week (week of Sep. 14, 2020), right. I got this crazy text. Well, okay. So backstory. Right. So I would say three weeks ago, I got this text, from my cousin. I’m going to read it to you one second. So I got this section, my cousin says, “Hey Theo, this is your cousin Jessica just wanted to let you know, I saw your promo for Sirius Lee. And I think it’s such a cool and original idea that, especially in 2020, there’s nothing else like that character in much needed comic relief considering the weight that’s been on the country. When I think about other characters we’ve seen on screen historically, especially of color, and there’s never been a Sirius, so kudos to you for your creativity and doing something you love to do. It says a lot also kudos to your wife for staying with me.” Right. So I got this really nice text from my cousin, Jessica. Last Monday (Sep. 14, 2020) I get a call from my dad late at night. He’s on the East coast. Hey, your cousin, Jessica just passed instantly, right? Like she’s 34. She was 34. She has three little children. Yeah, I mean, I’m still like, I’m still struggling with that. Like COVID, he’s on the East coast. I’m not able to get out to, I, I wasn’t able, I missed her funeral was yesterday (Sep. 23, 2020), you know, I’m just seeing pictures. and yeah, so like that’s another, like, it’s like, I, you know, I got that and it’s like, I have all these screenings coming up with canceled the screenings. So I stopped doing that or whatever, but it’s like literally she, she, a week and a half before had sent me an amazing tax, like supporting me and encouraging me and telling me how important this was. So I’m like, why would I, why would I stop? You know, I don’t, again out those that that’s what makes sense. So, you know,

Laisa: Was, did she also as the other two?

Theo: No, no, she was it was just sudden she, she had like, basically I think a blood clot, cause she had some, some, some like issues at her last child. I think there was a blood clot. Taking, you know, medication for it and stuff like that. But I think a blood clot got into her heart. She had like a heart attack and she died. Um, and, uh, yeah, no. So that’s like I mean, I don’t know. I’m still trying to figure out how to cope with that completely, but I’ve been talking to a therapist that’s dope, hard about right now and like all the therapy and stuff that, that is offered, you know, I was able to kinda get on, or my company helped me to like get therapy, like right around all this COVID stuff too. And I’ve been talking to a therapist and, you know, She’s like, I think you’re, you know, even if you’re not crying, like you’re creative. So like maybe that’s how you kind of deal with the pain and stuff. So I dunno for me, the first thing I did, I don’t know it’s small, but the first thing I did was I pulled all the festivals. I sent the film or the series to it. I was like, “Hey, I’m sending you another version of it.” Cause I went back in and I edited the credits and I put in memory to her and the credits, you know, and I, I like, it’s always nice, like seeing it on the big screen last Saturday and getting the, getting, getting to see her name up there for a, you know, for an extended period of time. And, I don’t know, like, I just, I think that for me, like, even though my art may be silly to other people, but it’s still like my way of kind of expressing like serious things and honoring the people that aren’t here for it, you know, aren’t here still. So, yeah, I don’t know, like, those are, those are some kind of heavy things that have been going on but you know, making through it and, I don’t know. I think, I think, the last time we talked you were even talking, I got to go back to watch Up cause you were talking about how that movie is really good with, like explaining how to deal with grief. And I think that that might be something good to watch. Now. I’m also kind of really into, interested in seeing Soul, but that’s got me nervous now, too, because I don’t know about you, but I’ve been, there’s just been a lot of deaths recently and I’m like, I feel like for me right now, this is like the items, like my career goals. And from what you’re telling me about. So it’s like, yo, he died and shit. So I’m like, yo like, I’m trying to like live everyday to the fullest and, and like, not worry about that shit, but scary out here right now, you know?

Laisa: Yeah. Yeah. And I just wanted to send love to you and your family. thank you for being brave and sharing this with us. I really appreciate that. And it’s a topic that’s important for, you know, everybody to be comfortable talking about because it is affecting everybody. People are losing their families, and their friends and, just not talking about it can make it really hard on us. So thank you for sharing that and thank you for being open about therapy, because that’s another thing. I also see a therapist now. But, you know, those are things that we have to like take into consideration because we are all affected in, in many ways. And we need, when we need the help, we need the help. It doesn’t mean it’s a bad day and it shouldn’t be stigmatized. So thank you. That’s it just shows a lot that you’re able to show your vulnerabilities with us. So I really appreciate that.

Theo: Indeed. Thank you.

Laisa: And just to close on a, just to close up, I would love for you to give any advice for young filmmakers, producers, writers. What would be something that had you would have had a mentor tell you, or something that you have applied to yourself for you to keep going into this career?

Theo: Hmm. Yeah, like I think that, I guess it’s near, it’s, it’s weird to say to young people, but I think it’s something to keep in mind as you age is to surround yourself with young people. Right. I think that, there’s a lot of folks, like, especially when he gets around like 30 and stuff like that, like your peers and stuff, you’re like, “Oh, I’m 30 now I’m too old to do that. And too old to do this, I won’t do that.” Right. They cut themselves off from opportunities or pursuing their dreams because they felt like, because they reached some invisible age feeling where they feel like they, that they, the things like. That they want to do or their passions or whatever aren’t achievable or aren’t realistic anymore. They’ve got too many bills to pay and too many other like adult concerns. And I’ve, I’ve definitely been kind of victim of that in the past. I think that like, kind of like when I first moved out here to the Bay Area, I like I just got a safe job. I worked in tech, I wasn’t being very creative. And, I was like kind of starting to like, use like some of my hunger for like my film career and pursuits and getting pretty complacent. And then like kind of, I kind of took like a leap of faith. And I was encouraged to like, like I found out about this job and at Baycat, which, you know, strange young adults and video production. And then, we also have a youth academy. And so I feel like being there in the past two years, just kind of like revitalize my creativity. And I found, and I think a lot of that energy and that revitalization is just come from being around young folks. You know what I mean? Who are like not afraid to like, they, they have less of a concern of failure or whatever, cause they haven’t maybe had as many experiences so that some of the failures are, you know, it’s like, they don’t know what’s going to come. So they just kind of won’t pursue anything without, without the light, you know, with records about, which is like kind of nice to do what you have to do with the filmmaker. Right. Sometimes like, just to kind of accept that there’s failure, you know, but that’s what we stop you necessarily. And I think that like surrounding yourself with young folks, you know, and, and always having a young energy, figuring out how you can have that energy or will help you help you help to sustain you. Even if the money is not always there, you know?

Laisa: Yeah. Thank you so much for sharing that. I love it. And thank you for your time here today. I really appreciate you and all of the knowledge and w- I just feel wiser now, but, thank you so much for everything that you have shared with us today.

Theo: Indeed. Indeed. Can I just plug real quick? If you’re interested in this series just follow us on Instagram @siriuslee_series. And then if y’all want to just check out, because I do other stuff other than that, if you don’t want to just check out samples of my other work go to theohollingsworth.com.

Laisa: Yes. All right. Thank you everyone. Bye.