With the script in tow, it was time to figure out the world for the film, and that meant capturing the true spirit of Chicago, Illinois. Given the party involved, that didn’t prove too difficult.
CUSACK: I think we were just showing off different parts of the musical scene that is kind of now changing even as we speak. So, it was a portrait of a time in Chicago, and it was nice to capture that era of Chicago. Some of it’s still here, but like The Double Door, the club where Jack Black’s singing Marvin Gaye at the end, that place has closed down. Gentrified. The Green Mill is still there; there’s some other places. I felt very good being in a city that I know so well and having the movie sort of wrapped around it with the architecture.
DEVINCENTIS: In pre-production, I was really, really excited about sinking this into the Chicago that I knew. And that meant taking Stephen and the production designer around to the record stores that I bought my records at and still did at that time. And modeling the record store on that record store. Also apartments of my friends. I took those guys into so many different houses and apartments to show them what average people who were going to Lounge Ax lived like. I took them to clubs like Lounge Ax, which was owned by a friend of mine, Sue, who is the wife of Jeff Tweedy. At the time, Wilco was not a big thing. But she owned Lounge Ax, which is the venue where Lisa Bonet plays in the movie. And we were like, “We’ve got to shoot it here. We’re not going to take it to another club. We’ll shoot it where these people would actually play.”
KORETZKY: It didn’t seem so much connected to the Chicago music scene as to music scenes in general as a thing — and made that a positive thing –which is a remarkable feat when you consider how nightmarish local scenes can be!
DEVINCENTIS: We were shooting on Lincoln, outside Lounge Ax, and I pointed across the street to the Biograph Theater — to the little alley next to it. And I said, “Stephen, see that alley?” “Yes.” “That’s the alley where they shot John Dillinger to death.” He’s like “What?!” “Yeah. And you know what happened? His fucking girlfriend tipped him off. She tipped the cops off, and that’s how they caught him and shot him dead in that alley.” And he’s like, “Well, why isn’t that in the script?” I’m like. “What?!” “Put it in. We’re shooting that!” “Okay.” And it’s in the movie.
PINK: We were very blessed to have the support of the studio at a time when it wasn’t that cheap to go to Chicago to shoot a movie of our dreams. We fought to shoot it in Chicago. We wrote it for Chicago, we shot the places we wanted to shoot, we were able to create the world of this movie through our own eyes, basically. Having that be our stomping grounds for so many years, and then being able to go shoot a movie in our stomping grounds, and then express it in a very particular way like, “This is a cinematic expression of our stomping grounds,” to me, it was just crazy. It was surreal how awesome that was.
HORNBY: That’s the brilliance of their adaptation. Because they came from Chicago and did all the touches. They absolutely knew not only the record culture but their alternative Chicago record culture. So they made it their own and they made it specifically about that city. And that is exactly what you want in an adaptation. It was rooted in there.
Now that pre-production was underway, it was time to start the casting process. Rob had been written, naturally, with Cusack in mind, but it was filling out the rest of the cast that would prove challenging.
FREARS: John was sort of grown up by this point. When I did The Grifters, he’d be very good for about two hours a day. And then you’d eventually arrange that day’s shooting around those two good hours. By the time we did High Fidelity, he was able to take responsibility for the whole film. So he’d grown up. He’d become much more adult. But he was very well cast. I always thought, For a film with this novel, he’s a really good guy to have. So I don’t remember him being particularly difficult. He was absolutely passionate about it. He just adored the material.
CUSACK: You’re always like, “This is a good role because there’s good overlap and he’s similar.” But I think that mostly I thought that if men were in a room and were given truth serum, they would probably tell you all that stuff. So I think it’s universal in the sense of … I’m not an OCD collector type of person. But in other ways, I’m a lot like him.
FREARS: For Barry, I said, “Who should play this part?” And the boys said, “Jack Black.” And I said, “Who’s he?” And he came to see me and I said, “Well, you’ll be fine.” But I didn’t really know a great deal about Jack. And then, of course, he was absolutely brilliant. Brilliant. But I didn’t quite know what to expect.
DEVINCENTIS: John, Steve, and I had known Jack Black forever from The Actor’s Gang. And we had watched Jack be Jack everywhere from Canter’s Deli to tiny theater stages in LA. We were very familiar with him. And just mentioning Jack, between the three of us, would make us laugh.
CUSACK: As soon as I read it in LA, I had seen Tenacious D play because I knew Tim Robbins and The Actor’s Gang and Jack was around there. So, I already knew that he was a great musician and singer and a great comic actor who was about to explode. But I felt like I had this secret weapon because no one really knew that he could rock that much. So the book was perfect and I thought, This is the perfect role for him.
PINK: I remember it being a no-brainer. When you’re that age, you’re just so supremely confident about everything. So I don’t remember thinking anything else except not only that Jack was perfect but that he was going to do it and anyone else that didn’t see it just didn’t get it.
JACK BLACK (“BARRY”): I don’t read books unless I really have to. Then once I got the part, I thought, I better do my research, my due diligence. So I went back to the source, and I thought that the screenplay stayed true to the spirit of the original text. But I was just worried that, at the time, Tenacious D had a full head of steam, and we were getting great crowds and were playing to big houses. And I had, in my mind, a legitimate rock and roll career, separate from film and television, that I wanted to protect. And to do a movie about music, playing sort of a music critic and talking about some of my heroes like Kurt Cobain … just all those elements made me nervous about messing with this thing that was my own little crown jewel of my life and career up to that moment. I was hesitant to fuck with that.
DEVINCENTIS: It was very mysterious. We were getting all this pushback. And he asked if he could audition. And Stephen was like, “I don’t want to do that. That’s a joke. I want him. He’s the guy. I don’t want to fucking audition him. I’ve already hired him. This is crazy.” He was amused by it. But he was like, “No. I’m not auditioning him. I know he’s the guy.” And it was really, really hard to get Jack to do it. And you’re thinking, This is the role that can change your whole life. You could feel it. And then we came to realize, or I did anyway, Oh he’s frightened of doing this because he knows this is the role that is going to change his life.
CUSACK: At first, he might have just been frightened by the whole big, high-pressure film and Stephen Frears with Working Title. And maybe he was a little intimidated by that. And then I had to tell him, “No, it’s going to be fun.”
BLACK: If I’m really being honest with myself, I was terrified of failing. I was terrified of being bad in this movie and also terrified of working with Stephen Frears. I had seen Dangerous Liaisons like 12 times, mainly because I was obsessed with John Malkovich. I really wanted to be John Malkovich. But he was clearly a master, and I was intimidated that I wasn’t good enough as an actor to pull it off. So I said, “I’m gonna pass.”
But Stephen called me in, even though I had passed. He said, “Get in here. I want to talk to you.” We talked about it a little bit. I told him about my fears, and he just thought it was funny that I was passing. Because it was obvious to him and to anyone in my life that this was a no-brainer. And it would be a huge mistake to bail on it for any reason other than I just didn’t like it. And that was not the case. I loved the script and I loved Stephen and I realized that I was just passing on it out of fear. And that was not a good reason. And so I said, “Okay, I’ll do it.”
TODD LOUISO (“DICK”): I guess I auditioned for the casting director. I had been acting for a while anyway. And then I got called back to read with John and meet Steve and DV, and so then I read with John, Steve, and DV and Vicky Thomas was the casting director. It went really well. And then when I went back to meet with Stephen, it was great. I didn’t even read, really. He just sort of met with me but then also walked around me as I was sitting there and just looked at me. Like I was on display or something. [Laughs.] But it was great. He just wanted to talk, which as a director myself, I like doing also. Not necessarily reading people but just talking with them and meeting with them to see what kind of person they are.
FREARS: I remember seeing Philip Seymour Hoffman and I kept saying, “I don’t know which part he should play.” And then we found Todd Louiso, who is brilliant.
LOUISO: They had also offered the part to David Arquette first and he passed. So then glory came.
PINK: The thing about Todd that I loved so much in High Fidelity is that he is Jack Black’s perfect opposite number, and I think that would’ve been hard for any other actor. We got really lucky with Todd. Obviously, Jack Black is Jack Black, and he’s extraordinary in the movie, and he is who he is because that’s who he is. But Todd was almost like this Yin to Jack’s Yang in a way that had so much authority. Jack could pick on Todd all he wanted, and Todd was kind of an unmovable force of heart. He was kind of this force of serenity. He also was a music snob like the rest of them, which made him still part of this club of music snobs. But beyond that, he had this genuine heart that could not be diminished by Jack’s insanity.
FREARS: I couldn’t find an American actress for Laura. And I kept saying, “Well, if you cast so and so, she’d be like John’s mother.”
DEVINCENTIS: We’re like “What!? She’s younger than John. What are you talking about?” And he’s like, “No, that’s not what I’m saying. The character, his immaturity is so delayed. He’s immature. And this actress has a presence that feels much older than him. She’d have no reason to be hanging out with him.” It was this very difficult needle to thread.
FREARS: And then I was at the Berlin Film Festival, and all the jurors said, “Oh, go and talk to Iben. She’s really good. She speaks English.” And I remember going to talk to her and you feel like Harvey Weinstein. “Would you like to be in a movie?” [Laughs.] But then I remember taking John over to meet her and then taking [producer] Tim Bevan over to meet her. And they said, “Well, she’s terrific.”
IBEN HJEJLE (“LAURA”): Well, the thing is, I wasn’t approached. I had approached Stephen with my friend Søren [Kragh-Jacobsen], who had directed the Dogme film that we were there with. And we had looked across the room at this great, big celebration thing, and we see Stephen Frears and I say, “That’s the director of the greatest movie ever, Dangerous Liaisons.” And my friend said, “That’s the director of the greatest movie ever, Gumshoe.” So we argue about that and he says, “Why don’t we ask him what’s the best movie he ever made?”
And so, we walk up to him and we talk to him for about five minutes, and then Stephen turns to me and says, “So you think you can act in an American accent?” And I say, “Absolutely, sir.” And I had no idea. And he said, “I think I have a part for you in my next film. Can I please call you?” And somebody gave him my private number on a matchbox. I didn’t expect to hear from him ever again. And then a week went by after I came home and he called me and said, “So, I would very much like to send you the script and the book that the script is based on.”
DEVINCENTIS: So then [Stephen] comes back and he’s like, “I’ve found her.” And we’re like “Okay.” He’s like, “She’s Danish.” We’re like “What?!” But you know, we all trusted Stephen so implicitly and he’s incredible at casting and incredible at discovery. If you look at the people that had their first meaty role in a Stephen Frears movie, it’s remarkable. It’s fucking crazy all the people that he’s introduced us to. So we’re like, “Great. Let’s check it out.” So Stephen and John flew to Denmark to read with her. What I was really waiting for was what John thought. That was the big decision to be made in my mind was that John liked it and if it felt right to him. And John came back, and, sure enough, he thought it was great. He loved her. He thought she was perfect.
HJEJLE: John Cusack, Stephen Frears, and the casting agent from London flew to Copenhagen to meet with me, because my son was so young — he was about a year old at the time. So, we went to a place and we shot a couple of scenes with Stephen and the casting agent on a camera — and we had so much fun. We were laughing. He was just so easy to work with and just a joy. Really a fantastic guy to hang out with.
PINK: And we had to write to it, that she was Danish. We had to write that into her backstory. In that scene, where she goes to the funeral, you can see they’re all very Scandinavian. Like her sister, her aunt, her mother. And we had to kind of lean into the fact that she was an alt-punk rock girl.
DEVINCENTIS: I remember that we initially focused on the possibility of finding a real singer to do the role of Marie. Like a musician. I was really pushing for Liz Phair because she and I were old friends from North Chicago. And I thought Liz would kill it. She became one of the more important musicians to come out of Chicago in the ’90s. So, we actually had a read through of the script in Chicago with Liz reading the role. We did it at Joanie Cusack’s house. And she was totally great. And we’re like, “She’s an actress. Oh my God.” But it wasn’t right for the role.
PINK: In the book she was like this American singer-songwriter. So, we were trying to think about, “Who would be outside of Rob’s reference level?” Because we wanted her to be mystifying. Well, if it was Jewel or someone like that, that wouldn’t be odd to a white dude in Chicago. So, we wanted to find someone who could play it with this mysterious quality that he could be awed by, who was also in the music world. And I don’t remember how her name came up, but I remember thinking it was brilliant.
FREARS: We had a lot of trouble casting that part. It was the hardest part to cast. I can’t remember why, but it was. Just that particular one. And I just knew her as an actress. I didn’t know her history. But she was great. She was really good.