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Any modern music connoisseur worth their salt knows how vital and influential singer-songwriter Will Oldham's melancholic, Americana-tinged output is to the indie-rock pantheon, whether he's recording under his own name or one of his countless monikers: Bonnie "Prince" Billy, Palace Brothers, Palace Songs, Palace Music, et al. Oldham also stars in Todd Rohal's The Guatemalan Handshake (now available on DVD), which is hardly the first time this 37-year-old icon to hipsters everywhere has flexed his acting muscles. In films as diverse as John Sayles' 1987 mining labor-union drama Matewan and recent cult faves like Junebug and Old Joy, Oldham's sporadic acting gigs are as unpredictable, memorable and even as eccentric as his music career. As a favor to both Todd Rohal and his friends at Benten Films, filmmaker Michael Tully (Silver Jew, Cocaine Angel) spoke with Oldham about The Guatemalan Handshake, collaborating onscreen with R. Kelly, and his peculiar theory on where found treasures come from.
Before we delve into The Guatemalan Handshake, I'd like to first know more about how you came to appear in R. Kelly's Trapped in the Closet, and what that experience was like compared to the more conventional acting you've done in film.
It came about through this weird convoluted process. The actor Nicky Katt had told the director Richard Linklater that he should check out some music of mine and Matt Sweeney's, and he did. He was also friends with Caveh Zahedi, who I had done this mushroom-tripping short film with, so [Linklater] said, "Do you want to do some music for Fast Food Nation?" I had heard good things about the book, and I liked his movies, so I went to Texas to watch a cut of it. There was this scene where people were acting their hearts out, and on TV in the background was Trapped in the Closet. When it was over, after everyone did their critiques of the cut, I took one of the producers aside and asked, "Why did you have Trapped in the Closet in there?" She said, "You knew what that was? Oh my gosh!" And we started talking, because she produced the video and was close with R. Kelly. I told her that he really means a lot to me, and we had done this cover of "Ignition, Part 1." She was psyched about it.
I kept in touch with her, and she got me tickets to see R. Kelly in Chicago that summer, two years ago, and it was one of the best shows I'd ever seen. A few months later, she told me they were doing more [episodes], and would I have any interest in playing a cop in one of them? In two days, I was in Chicago at R. Kelly's house, at rehearsal. He was super-kind when I got to his house; after a few minutes, he put his arm around me and asked, "You got everything you need, baby?" We rehearsed on Saturday and shot on Monday. It was fantastic, because there was a nominal director who acted more like a producer, or wrangler. R. Kelly was the guy who was into everybody and telling them their motivation, giving them facial readings, talking about their characters, and blocking. It was really exciting being around him over the course of that weekend and just watching the way he rolls. It was magical.
I realize that your Guatemalan Handshake experience went down quite a while ago, but do you remember what led you to take that plunge with Todd Rohal?
He had worked with [filmmaker] Diane Bellino, who I was really close with. She liked working with Todd on a project of hers. He sent a script and a brief letter outlining what his hopes were, what was gonna happen, and where it was gonna be. I have a fondness for working like that, where there's a strong eye on professionalism, but that's not the rule of how it's structured. It is defined by the character of the people involved, and not by unions or how things ought to be done. So, [along] with Diane's endorsement and the other shorts he'd done, it seemed like I couldn't lose in it being a learning experience.
How did the finished version of the film compare to your early expectations while working with that team of collaborators?
When you get into something like that, it's fully with the understanding that you're there as a supporting part of the whole, so it's somebody else's deal. My [only] expectation is that -- if they know what they are doing -- they will use mine and everybody else's presence to the best, and the only way to know what the fuck they're doing is to either sleep with them for six years, or wait till it's over and watch it. One thing I became a big fan of a long time ago is when I can feel like I'm watching the making of the movie while I'm watching the movie. That's so exciting, which is why a movie like Irreversible, which some say is so harsh and fucked up... I could leave it completely exhilarated. To me, it's about how exciting [the process] was, and not rape or whatever. The ultimate movie like that is The Misfits, with Clark Gable, Marilyn Monroe and Montgomery Clift, seeing that it's about everything those individuals are about, all of them coming together and making a movie. In that way, at least, The Guatemalan Handshake totally succeeds.
Are you much of a media collector?
Yeah, I definitely have shelves of records and CDs and movies. I feel less precious or devoted to the DVDs because it seems like that format has its time. In terms of when I was born and when I’ll die, records and CDs will probably have a longer life than DVDs. With books, if it's a really nice copy, I feel I can trust it because I can always pick it up and read it. If it's a DVD, I think, "This is nice, but why did they spend so much time on it?" This is great for now, but in 20 years, I might not be able to show it to my kids, nieces and nephews. They’ll look at it and be like, "That's a neat-looking thing, what the fuck is it?" One day, we could watch these things. But at least with CDs, you can turn them into files. I guess you can do that with DVDs. [You can] make the packaging nice for now, but understand that it's temporary.
One of your earliest performances was in Matewan, which takes place in a small West Virginia town. 20 years later, you worked in small-town Pennsylvania on The Guatemalan Handshake. Were there any similarities between the productions?
Yeah, the quality of the crew on both was very high, and that was really exciting on that John Sayles movie. It seems the producers and Sayles put together a crew based on skill and personality, and it made the whole thing so much more enriching. And that seemed to be the case with The Guatemalan Handshake, where it was nice being with everybody for who they were: they spent half their energy on being who they were, and half their energy being good at what they did. That’s how they were similar, otherwise they were very different. The Matewan production was some kind of offshoot of a traditional union rules film-shoot structure, and The Guatemalan Handshake wasn't that way at all. It was more like: I had a car so therefore my car was in the production. I like that.
Have you ever thought about writing and directing your own feature?
I don't think so. The prospect of that much money -- the amount it takes to do the most basic film -- is really daunting. Also, I have a real hard time communicating my ideas. Therefore, to work with a large amount of people... I like talking to people one-on-one, or one-on-two, or one-on-three, but once you get into shooting a scene, you've got more people than that. Making records is nice because I can see when miscommunication is happening and can attempt to address it right away. I worry that there's too many loose threads 
in a film production.
In 2001, you presented Timothy Carey's The World's Greatest Sinner at the Maryland Film Festival. In all the digging you've done for obscure films, is there anything that you feel is underappreciated?
There's nothing I think should be seen more or heard more. That's totally up to the audience. I've never understood the concept of things being underappreciated, for the most part. If something has a strong audience of 10, would you rather it have a weak audience of 20? The great thing about the Internet is that people have more access to things that are going to be important to them.
Dan Osborn of Drag City just sent me all these DVDs of movies that aren't properly in print. A couple of nights ago, I watched a movie called Ladies and Gentleman, the Fabulous Stains. Diane Lane heads this Shaggs-like punk band that opens for a British punk band called the Looters, which has Paul Simenon and Steve Jones and a young Ray Winstone as the lead singer. They're opening for a KISS kind of band, but when the lead guitarist dies of an overdose, the Looters become the headliners and the Stains start a revolution with their slogan "We don't put out."
Who directed that?
Lou Adler, a big L.A. record producer [who worked with] The Beach Boys and Carole King. Christine Lahti is also in it, and Laura Dern. Weird things like this come up, and I think, "Why didn't I see this before?" I have one theory that God likes to surprise us by inventing things over the course of our lifetime, then inserting them in history. So you're like, "Why did I never hear this record before?" and it's because God invented it that day just to throw you. But He also planted it in everybody else's brain except yours, because that's the only way certain things could have escaped your attention all your life.
Has a movie ever made you well up?
I cry on planes, most of all to movies. The first time I realized something was fucked up was crying to My Giant with Billy Crystal and that Eastern European. I bawled during that, during Lilo & Stitch -- that Disney extraterrestrial cartoon in Hawaii -- and a couple of days ago to The Great Debaters. I cried really hard at that one with Julie Christie as an Alzheimer's [sufferer]. That was the hardest I probably cried since E.T., back when it came out.
You’re working on so many projects in different mediums. Is it important for you to mentally delineate between them, to keep things compartmentalized, or do they all comfortably blur together?
When I can find some kind of inter-relation or correlation, whether or not that makes [sense] to anybody else doesn't really matter now. It may one day, or it may not. Doing something like The Guatemalan Handshake would be more along the lines of singing with Björk for the Matthew Barney movie in that it's trusting that somebody knows why they want me to do something; feeling the freedom of not needing to worry about the end, what the end is, and getting to use some skills or muscles that I've been exercising by making records and doing shows. In that way, those are similar. Whenever someone asks me to be a part of something they're doing, that's one kind of [project], and when I'm doing something [myself], that's the other kind. Whether it's film, video or music, those are the delineations.
For more info on Benten's DVD release of The Guatemalan Handshake, click here.