The following Q&A took place following the world premiere of Isiah Medina’s Gangsterism at the Paradise Theatre (August 29 2025) in Toronto, presented with CONTOURS / Saffron Maeve.
Saffron Maeve: I’m so pleased to welcome everyone to the World Premiere of Isiah Medina’s Gangsterism. Firstly, thank you so much to Isiah and Kelley Dong for bringing this film to the series. I first met Isiah because he was frequenting Contours last year, so it’s a lovely full circle moment to be presenting this film. At the end of every season, I like to present the next season’s titles live, so I’ll quickly announce my fall lineup at Contours for you all. On September 21st, I’m showing the Czech anthology film Pearls of the Deep; on October 5th, Herschell Gordon Lewis’s Color Me Blood Red; on November 2nd, Bergman’s Hour of the Wolf; and, finally, on December 7th, Kenji Mizoguchi’s Utamaro and His Five Women.
Now, a bit of background on tonight’s director: Isiah Medina was born in Winnipeg and currently lives in Toronto, where he directs and produces films with his company Quantity Cinema. His features include 88:88, Inventing the Future, Night is Limpid, He Thought He Died, and Gangsterism. His films have played at the Locarno Film Festival, New York Film Festival, TIFF, Mar del Plata International Film Festival, Jeonju International Film Festival, Berlin Critics’ Week, QCinema, International Film Festival of India, São Paulo, Cineteca Madrid, Erarta Museum of Contemporary Art, Centre Georges Pompidou, and on YouTube. [Cheering]
In my own curation of this series, I’ve often felt both spacious and confined by the thematic core of “visual art”: painting, sculpture, illustration, but rarely industry, commerce, crime—the social periphery of art I’m most interested in. Gangsterism innovates not only formally, with cuts that feel like sleight of hand and compositions that resemble stately paintings, but offers new dimensions to the work I wish to do, and I’m grateful for that. This film—which follows a director-gangster (because the one is so often the other) collecting overdue funds—is revealing in what it communicates about disillusionment, exhibition, propriety, and fascism in Toronto’s filmmaking landscape. It is truly impressive how the film manages to both absorb and organize our anxieties—not simply acknowledging how racism or genocide infects us as social beings, but how blatantly it limits our capacity to engage with art and culture, and this is by design.
Around this screening, I’ve been thinking about another film I’ve programmed in the past: Vincente Minnelli’s Lust for Life, about Van Gogh. Particularly one scene, where two now-prolific artists are arguing over craft. “With all your talk of emotion, all I see when I look at your work is just that you paint too fast,” exclaims Paul Gauguin in this scene. A fraction of a second later, Van Gogh responds, angrily, “You look too fast!” Gangsterism is a film that moves fast but invites us to look slowly, sculpting and arranging time in the way that Isiah has done for the better part of a decade.
After the screening, there will be a Q&A with the director moderated by writer and critic Winnie Wang—that’s a real treat, so please stay put afterwards. Now, please join me in welcoming Isiah Medina. [Applause]
Isiah Medina: If you were part of the movie, as an actor or a crew member, please stand up or put up your hand. Thank you for making this picture with me. Now let’s watch it.
Winnie Wang: Yes, I am dressed like Clem on purpose. I asked Isiah to lend me the tie. Isiah, what are you wearing?
Isiah Medina: Oh, seriously?
WW: Yeah.
IM: This is Fall/Winter 2021, Hood by Air. [Cheering] It’s a Shayne Oliver masterpiece, I wanted to get it. I couldn’t afford it in 2021. So I just waited and waited and waited. And then when it was like, I was like one week away from finishing the movie. And I thought I deserved to get myself a grail because I thought the movie was good.
WW: Well deserved.
IM: And I knew I’d wear it to the first screening. You know what I mean? And like, yeah, I really liked the idea. I think this relationship with hood and prep is very me, so I wanted to wear it.
WW: Thank you for sharing. I wanted to begin with your title, Gangsterism. Becoming a gangster requires being initiated into a society with its own rules and leaders and organization, much like citizens of a country or state. And I think your film is interested in some of these parallels. Could you talk about where the title originated and where your interest in the figure of the gangster comes from?
IM: I just love gangster movies. I grew up watching gangster movies all the time. What I like about gangster movies is that they’re the ones where you watch it and you try it out in real life. Everyone always acts like, oh, does cinema affect reality? Are you kidding me?
Like, when I watch a gangster movie, we’re going to do something after for sure. [Laughter] And I think it’s an honest relationship to cinema. I mean, it’s like how we try to think about philosophy. Does philosophy relate to life? Yeah, cinema, like gangster pictures and romance—rom-coms are like the ones for sure it relates to life. Because you watch it, and then you’ll give it a shot. And the title, like, I don’t know, I was reading Last Tycoon and it came up once. Ooh, that’s nice.
And then I remembered Alain Badiou used the word gangsterism to describe capitalism—that’s nice. And there’s this beautiful painting by Basquiat, “Hollywood Africans”, and the word gangsterism is on it. And I just liked how it had to do with cinema. There’s like a seven star rating, all these little jokey stuff. It’s gorgeous. I just kept hearing gangsterism. You know, once you lock in on something, suddenly gangsterism starts appearing everywhere.
So that’s where the title came from. It’s like, okay, this is another joke. You know how Scorsese will always be like, yeah, it’s a critique. It’s a critique. Are you kidding me? Like when I watch Wolf of Wall Street, I’m going to party right after. [Laughter] But it’s serious because Jordan Belfort said he got inspired because he watched Goodfellas. I just think there’s a really real relationship between cinema and reality that I don’t want to take for granted. And the figure of the gangster, too, because they bring in philosophy.
Socrates was a criminal and he died because he was corrupting the youth and showed impiety to gods. So these are some things that made me want to make a gangster movie. And I thought the gangster movie would allow me to say anything I want on screen.
Because, like, you know, watch a gangster movie. The gangster can say anything they want. And you always think, well, he’s a criminal. I guess he’ll say that. So it just allowed me to say anything I felt like putting on screen, I could do it. But same thing with Socrates, too, right?Whether it’s Joe Pesci in Goodfellas or Socrates, you can say what you want. And I love that.
WW: Favourite gangster film and favourite rom-com?
IM: Woah, okay. [Laughter] Favourite gangster film. Okay, I’ll have to go to the rom-com first, actually. Recently, I saw Howard Hawks’ Man’s Favorite Sport?—couldn’t believe it. I watched it, like, literally a couple days ago. That might be it. But I also adore Notting Hill and She’s All That [Cheering]. For gangster pictures, I’d have to say Godfather III, for sure. [Laughter]
It’s like the first one that pops up in my mind. I mean, Once Upon a Time in America is in this one, too, for sure. Yeah, but for some reason, I’m onstage talking to you, Godfather III is the first thing that came up. I think we should just leave it at that, maybe. Oh, I like Howard Hawks’ Scarface. I like De Palma’s Scarface. Really good. Yeah, I’m going to keep naming gangster pictures, we should just stop there.
WW: Something more earnest—
IM: Oh, it’s earnest.
WW: [I mean] my question, more earnest. There’s this line in your film that goes, “I didn’t know love didn’t have to be colonial.” I was really touched by this. And I’m curious about how you define colonial and non-colonial relationality or love. Did filmmaking figure into how you realized this or understood this? I know that you often work with your friends, or your actors become your friends, and you have a reputation for running sets in a way that you end early, and you have nice lunches that are long, and so it feels non-extractive. It’s a different mode of making.
IM: Yeah, I mean, I just think I learned it from cinema, to be honest. Not even in a particular movie, necessarily. But this possibility, which is like a dream that will be real, to live in a non-property relation way with the world. And I just think it’s an important idea. And I think cinema is a place where we could start thinking it. I’m very serious about Eisenstein’s October, because obviously it signifies an event in human history where a people tried to live without property relations and private property. But also for his intellectual montage to work, you have to live without property. I have to be allowed to shoot anything I want, and I can’t really do that here. I can’t use any song I want, etc.
So when I think of non-colonial love, non-colonial picture-making, it’s related to this property question and how we live like that. And that’s why, at the very least, when we’re making the picture. Yeah, we’ll have a good lunch. We’ll relax. I don’t want it to feel exhausting to be on set. It should be fun. I mean, if you’re gonna choose cinema, can you at least have fun? I just feel like I hate this idea of people choose cinema, and it’s a terrible day on set, you overwork everyone because it’s going to be a masterpiece. Let’s be honest, usually it’s not. [Laughter] So why are you overworking everyone for what?
So I just think at that level, there’s too many concrete things we can do when you make cinema, because suddenly we get to try to invent some minimally utopian economic format. Like, this person gets paid that. We could decide the hours. We get to, like kids, decide how we want to organize our little society while we make this picture for X amount of days. So that’s something interesting, too. But yeah, just trying to think love outside of the question of property.
And even in mathematics, too, it’s like you could define sets via their properties and the properties they share. Or you don’t have to. There’s two ways. But I feel like if we start by thinking what they all share, then we get into language and we start naming things. And all of a sudden, it closes our mind. And I just think there’s a way to think love, etc, without having to refer to language right away. And that’s just one way to start thinking that non-property relation, because language is a question of things that are named and they have properties. So there’s other ways to go about it, I think. And I think cinema is a way to do that. Like Clem says. Because cinema started with silent cinema. So it shows you can think without language. And it’s not too mystical. Painting does it. Music does it. Mathematics does it. But I’m going to throw the dice and say cinema will be the best one.
WW: Continuing along the lines of the filmmaking process, this film touches on budgets and how much it costs to be an artist. I’d love to hear you talk more about your philosophy on this. What would you say to artists who feel like they need hundreds of thousands of dollars to make their vision come true and feel limited by their financial resources?
IM: Yeah, I’m fond of always saying it’s like a colonial trick. The budgets, whatever. Especially in the digital era, why are you complaining? It’s so disgusting. I mean, my first feature I made with nothing. Actually, I think it’s because a lot of people don’t have friends. But if you have friends, you have people you trust, you can make something with little, and that’s what solidarity is about. This other really simple example is that if you have $10 billion or $100,000, these are finite numbers, right? And if I have a finite mind, my finite mind will be divided by these finite numbers and get smaller. But if I have an infinite idea, no matter what finite numbers are thrown at me, there’s a subset that will remain infinite.
And I use this as an example to just say, like, if you have an infinite idea, you can do anything. But if you have a finite idea and a finite closed vision of the world, you probably will be on your hands and knees for budgets and money. But I think when a form of thinking is liberating, there has to be something about it that doesn’t necessarily require money. I’m not saying don’t use it if it’s around, if you can find a way to use it in an interesting manner. But the dignity of human thinking means it doesn’t have to do anything with money.
And it’s another variation of Socrates saying, all I know is I know nothing. You can with nothing, you can have nothing, and you can still think. Don’t let all this language trick you into thinking you are this other type of nothing.
WW: This film synthesizes a lot of your experiences and the ideas that you’ve been working on, this being one of them. I’m thinking about the stories that reflect your time on the festival circuit. And then there’s the line, “learning my grandparents’ language isn’t economically feasible,” which I remember from your Q&A at TIFF in 2023 for He Thought He Died. So I’m sensing a really strong autobiographical influence. Why is now, 10 years after your debut, the right time to make this particular film?
IM: Why this film after 10 years? Because I’ve been making pictures for 10 years. When I made the first one, actually at that time I was making pictures for 10 years too, because I was making pictures since I was a kid. I wanted to have the right to look at what that looks like, because when I see movies about making movies, it doesn’t look like that. When you’re a movie maker, suddenly you have to ask yourself, wait, why are my movies leaking? Who’s leaking that? And I don’t see that in the previous pictures about making movies, which I like as well.
Another question, because once you’re thinking of cinema, you’re thinking okay, what type of moving images am I surrounded with? But as a filmmaker, you have to ask yourself, why are we surrounded by images of genocide? And what are we going to do about that? So these are all just questions of what it means to be a movie maker. And it just seemed like it’d be a time to do it, because I’ve had experience making movies with money, without money, and I just wanted to think, okay, what does it mean to make movies in general? I find most movies are usually about making movies.
I like to use this example of Casino: It looks like a casino, but that’s a studio set that Robert De Niro’s struggling to run. Land of the Pharaohs by Howard Hawks. The pharaoh is building a pyramid. It’s a movie, right? [Laughter] So you have this other substitution thing. But if you make a movie about making movies, you have the self-referentiality that allows you to talk about anything. And I just felt like talking about anything, actually.
Yeah, and then it connects to this gangster stuff that I was really intrigued by. But also just because after making pictures X, Y, and Z, I just really want to reflect what it means to do this. Like, why do I wake up every day to make movies? Why am I doing this? Night is Limpid was kind of about criticism, and He Thought He Died was a bit about curation. So I wanted to make a picture about making pictures, and what that means to me, because what I’ve seen so far didn’t seem to reflect exactly what my life’s been like as a picture maker.
WW: Okay, this is my last question before I throw it to the audience. Some of those stories feel very specific, perhaps drawn from personal experience. In particular, I’m referencing the anecdote about an experimental filmmaker who mistook you for a cab driver after you edited his film. [Laughter] Who was that based on?
IM: That was Michael Snow. [Laughter] And that’s the last thing I’ll say about that.
WW: Any questions? Okay, I will ask more fashion questions.
IM: Please do.
WW: There are some really incredible costumes in this film. You’ve got the blue Rembrandt sweatshirt by J.W. Anderson. There’s a really good preppy number with the cream V-neck sweater. You have the line, “Europe has memories, America has T-shirts.” So clearly fashion is on the mind. Could you highlight some of your favourite pieces? What was your approach with dressing your characters?
IM: I mean, each piece has a different relationship to the montage, to the cutting. I collected the clothes over a couple years every time I was at, I don’t know, like, Value Village or a different store, and I see something like that, I’d think oh that’s so Gangsterism and I’d get that.
And then I started montaging my mind. Oh, I could cut from this shirt to that shirt, and these colours match, so I could do that. And then I’ll put tape on the wall that are these particular colours so it makes the cutting work, et cetera. But each thing has a different thing. For example, there’s the Yeezy Gap that Charlotte wears as March. I thought that was important to see. I like putting things that actually mean something to me in my historical time. I wanted to have that because he is an artist of our time, and I want to think about it. And I thought the type of picture March looks like she was working on seemed like an interesting picture.
And I was also thinking about the painter Philip Guston, and he had those paintings of members of the KKK doing self-portraiture. These are these beautiful paintings. Also I have this nice pink lighting in the film. It was probably unconsciously related to Guston, too. And I just appreciate those paintings because it’s such an image of, like, yeah, the art world is full of white supremacists, you know. But I wanted to think, what does that look like today?
Maybe they are wearing the Yeezy Gap, or maybe they just like it because of the way it looks. And I wanted to, like, work with all these contradictions at once because I think that’s what cinema is about. And that’s the part you talked about, which is like a JLG thing, where it’s like, yeah, Europe has memories, America has T-shirts. There’s a lot of memories in these T-shirts. That’s why you have the Pyrex, right? That’s why you got the Yeezy Gap, what these pieces mean to people.
Why does someone choose to wear a suit rather than this and that as a filmmaker? Especially as a filmmaker, I thought, you know, you should be in a suit because it’s a classical thing I grew up seeing, actually. And it’s really funny because all my favourite filmmakers are dropouts, and they’ll just kind of put on a tie to pretend. And maybe someone will throw the money at them so they can make the next picture. And I always thought that was a really charming part of making movies. [Laughter] But also, with clothes and movies, too, when you watch all the great filmmakers, a bunch of characters start looking like the director.
I use this example, like, in Rhapsody in August by Kurosawa, why are all the kids dressed like grandpas? [Laughter] They’re wearing fishing hats and the cargo shorts and this bigger tee and stuff. But I think that just shows how you put yourself really deep into the world so you could try to think it. And I think costume design is just one aspect of cinema where you try to put your ideas into the world so it can materialize. Because you don’t know what’s in your head. I’m not an idealist. To know what’s in my head, I have to put it outside and take a look at it and cut it together. I guess that’s what was in my head. So I try to put everything inside outside so I could re-internalize it via the cut, via the picture-making business.
Q1: What was the editing process like? Technically and in your mind.
IM: So with this picture, right after shooting it, I started editing immediately for two or three weeks. And I tried to edit all the major sequences. Kind of like the talk in the movie, like, sequence comes first. You know, like with shot-counter-shot—before that, there’s Kuleshov, which is like there’s a face, then an object. Kuleshov comes first, which is just a simple way to say thinking comes first. Thinking beings happen before speaking beings. So anytime someone’s thinking, and that’s usually sequences, where it’s like classic Hitchcock let’s say, you just have a sequence and no one’s talking. I did all the sequences first. And then because I went into this right after finishing two pictures, I was exhausted. So I partied for a whole year. [Laughter] Then once the partying was kind of done, went back into it and edited for like a month or so.
And then the process was kind of like waking up at 5 p.m., and then editing for a bit. And then eating, and then going to the gym at like 1 a.m. to 2 a.m. to break that up. And then from like 2 a.m. to 11 a.m., keep editing. And it’s because Frank Ocean has this Tumblr post where he said all posts between 3 a.m. and 7 a.m. are forgiven. [Laughter] And that’s the mindset I want to be in when I edit. You know, like the most like, you know, I shouldn’t put that out…but I’m going to put it in the movie. So I just want to be that mode when I’m making pictures, like as uncensored as possible. So that’s the time I like. I try to be a professional, do 9 to 5 editing. I can’t, but I can’t. I have to be in the nighttime. [Laughter] It’s the only way I can do this.
Then after I have the sequences, I only want to use just as much of the dialogue as I actually need. And I often end up finding out I used the first take, first or second take, because the actors are incredible. And like, yeah, all this other David Fincher, 900 takes, I’m against it, you know, because I’m against this overwork question too. And it just inspired me to know that my next picture, I’ll probably just do the first two takes and walk away, because I end up using like, yeah, take 5, 6, 7, 8, 9, they’re all great. And then I just kind of place these dialogue within the sequences. And this gets really abstract quickly, but basically then I have these like big four big parts, where it’s like a sort of type of infinity. I try to cut here. And then one’s opposed to it over here, it’s this lower infinity.
And I start having them geometrically interact. It’s kind of like what I was saying with the Kuleshov and the shot-counter-shot. But I make larger, big blocks of a pure thought, and another one, and I see how they slowly start to interact. So I see how those start to montage. So I’m not montaging the shot to shot, but like forms of thinking against other forms of thinking. By the end, I have like four big blocks that I have to slowly start blocking together.
Q2: Hello. Thank you for that. I was thinking of the line where it’s said that you want to reject the dialectic. And that made me think of almost like when Fanon critiqued Sartre for positioning decolonial thought as the antithesis to colonization as the thesis. And he says like decolonial thought should be affirmative in its own right, not tethered to a colonial referent in that dialectical format. But I guess my question is, in like a meta sense, isn’t the negation of the dialectic a meta-negation itself moving into that sort of place? I don’t know if that makes sense.
IM: Oh no, it makes absolute sense. The question, in fact, is that how do you start with affirmation, like you were saying, untethered by negation? But that question of negating dialectics isn’t the first thing, you know? That happens kind of like in the middle of the movie because all this other business started happening. So it’s more of the question that, for me, as a picture maker in the picture-making business, I genuinely think cinema is higher than philosophy. I thought after Godard killed himself that, okay, now we can finally say, rather than get in this Kant-Hegel relationship, I’m interested in like the eisensteino-godardien relationship.
Because they’re able to think like images and sounds, frames and cuts, and I think that’s where we are in this century. And it’s not going to be rereading German Idealism, I’m sorry to say. And I think it’s really important to me because when I think of seeing images of genocide and Jürgen Habermas can come out and say, it’s not, it’s not a genocide—using language.
But we all saw the images, and I try to think who helped me think images and sounds? And if I’m going to do something in the future of thinking, I really think it’s going to be there. And that’s why I named those two. So this negation of dialectics in this sense would come from that. So it’s not first. The negation of dialectics isn’t first. It’s this affirmation of this new power of thinking with cinema that I’m really probably betting my life on. That it could defeat all this philosophy of language because it thinks at a higher infinity. Language is a small infinity. Negation is later.
But it goes back to old questions of Plato saying, he’s about things, not words. Before Badiou had to prop himself up as this great European thinker, I do like in the earlier stuff where he said he tried to go against dialectics too, using mathematics as an anti-dialectical thought. There’s a moment there in like the late 80s and 90s. And then he abandoned it and started talking about materialist dialectics again. That’s how a lot of thinkers go. You like, you have a crazy moment in your mid career that you could have went any other path. And sometimes you kind of renege and go back to something you’re comfortable with, words you’re comfortable with. I’m always trying to fight that and follow the path that’s a bit more difficult, where it’s not really clear how to continue.
I’m really thinking that. Because some of these older questions of dialectics are not adequately keeping up with the mathematics of our time. So there’s new mathematics we have to learn. And we could think it with cinema, all these type of things. There’s a whole other form of how to think opposition, how we’re going to be free, etc. And I just really don’t know if it’s going to be with what we used to call dialectics, whatever name you want to use it for. I just think that I don’t want to get trapped in that type of question.
Like you were talking with Sartre and Fanon when he was basically accusing Sartre of being like a Hegelian suddenly, when he was doing some other interesting things. And I think that’s really important. We all know Marx’s critique of Hegel, this classic thing. I feel like suddenly in like, I don’t know, the 2010s, there was this huge regression in philosophical thought, and I’m guilty of it too, when we all thought we should go back into Hegel. But actually, after October 7, it was clear to me that no, we have to think outside the state. We got to find a way. We can’t keep going back to all this way of thinking about it after I see the images. I just didn’t think using language, the state is the end of everything. I’m just against it. I wanted to think something else because I saw different types of images. And there must be a way to cut this without throwing language on top of it and explaining it and making new justifications why the world exists as it is.
WW: Time for one last question.
Q3: Hi, great film. I just wanted to start off by congratulating you.
IM: That’s so sweet.
Q3: I really really enjoyed it. My question stems from the previous question, you said something that really threw me for a loop. You said you had this dialectical relationship between Eisenstein and Godard. For me, or the way I always thought of it, the dialectical relationship was more Eisenstein-Vertov, for me also by virtue of being contemporaries. So I’m curious, somebody that is as interested as you are with perhaps cinema as another type of language or moving on from spoken language to cinema, where does the kind of Vertov thought come in, in the sense of, or is he in—I just would like to ask you in general.
IM: About Vertov? Just Vertov?
Q3: Yeah, just Vertov. Sure, why not.
IM: For sure, for sure. I think when I was younger, I was really into—some of my early works that some people mistake for documentary have this Vertovian question of how to film reality and stuff, which I still think is important. I think my rom-com might have some Vertovian elements. But I just think there’s a necessity for me to think how to stage something, because when you’re staging something, you’re fighting reality. Either you get the permit or you don’t get the permit, but you still have to stand on that piece of land and make a picture.
And I’m not saying Vertov’s not looking for permits in the same way, but I just didn’t want to get in a situation where I was in my early work, where I’m kind of running around with my friends, shooting stuff, thinking about it after. But if I plan in advance how to connect all these questions and also not so much get out of reality—you know that whole thing where the classic opposition between alive and dead, and then you have the undead, which is a bit more. And I feel like the relationship between that, between fiction and nonfiction, is kind of like that, where I could think reality even more clearly with fiction. And that’s why my movies are getting even more fictional as I get older.
So that’s the relationship with Vertov. But I think because rom-coms are always, you know, a couple or whatever walking down the street, you know, might be some Vertov elements there. But I just think it’s more that the montage is happening at every single point.
Okay, here it is actually. Because reality is incomplete, I have to invent something to shoot too. And the thing with Vertov is that there’s this question, as if reality is already complete, I could just shoot it and then find the truth in it. But because reality is actually unfinished, I have to also add some new things into reality to shoot to finish the thought of reality as such. And that’s my critique of Vertov.