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“Nostalgia for When Things were Terrible”: Conner O’Malley, Danny Scharar and Jack Bensinger on Rap World
Rap World There’s an honesty to Rap World, the feature debut of co-directors Conner O’Malley and Danny Scharar, beyond its vérité stylings. With Scharar playing the director, Ben, Rap World is a mockumentary following three friends—Matt (O’Malley), Casey (Jack Bensinger) and Jason (Eric Rahill)—from Tobyhanna, Pennsylvania, as they trudge through one long night in a quixotic attempt to make a rap album. It is January 11th, 2009: a month earlier The Dark Knight was released on home video, in nine days George W. Bush will leave office, the Great Recession looms and America feels like it is on the cusp of some kind of change. But this is all of peripheral concern for the main trio: they’re plagued with overbearing parents, minimum wage bosses, custody battles and dreams of owning a hundred Corvettes. But their McMansion aspirations are mired by their procrastinations, so much so that it almost seems like an instinct to do anything besides make the album: hang out in parking lots, play with a gun found under one of their moms’ beds, go to parties they aren’t really invited to.
Rap World itself had a similarly procrastinatory story: its characters were created for a series of YouTube shorts that the team tried shooting in 2020 but weren’t satisfied with, shelving the idea for well over a year before picking the project back up in 2022. For the team, Rap World acts in hindsight as a document of a New York comedy scene that got frozen in place by the COVID-19 pandemic, briefly keeping a crew together for a little longer than they naturally would have before transplanting (mostly) to LA. This includes cameos from faces familiar to those wired on internet culture—Patrick Doran, Cameron Fetter, Caleb Pitts, Rajat Suresh and Jeremy Levick—but also standout side performances from Lauren Servideo, Edy Modica, Nate Verrone and Ruby McCollister. Even Sarah Sherman makes an appearance in a surprisingly sweet scene next to the dumpsters behind a grocery store.
In this sincere description of what the film is and what it might represent to the people behind it, I am failing to emphasize just how funny Rap World is. Everything from a mid-2000s radio-staple needle drop to a smash cut between scenes (besides just starring in it, Bensinger also acted as the editor) can rip your lungs out with laughter, especially in a crowded room. That is first and foremost what audiences will come to Rap World for, as O’Malley’s projects have developed an exponentially expanding following since the film began production. Yet the key with Rap World isn’t just O’Malley’s affinity for playing the likes of a lone nut yelling in the dump or a deranged vlogger in the Wisconsin Dells. Instead, the heart of it is in the collaboration, Bensinger and Rahill’s sensibilities dancing along with O’Malley’s, creating a real, hilarious magic on screen.
Ahead of Rap World’s drop on YouTube, I talked with Conner O’Malley, Danny Scharar and Jack Bensinger about the project over Zoom.
Filmmaker: When did Rap World get started?
O’Malley: 2020—October, COVID-19 pandemic—we got an idea for a series of shorts that would be me, Jack [Bensinger], and Eric [Rahill] making a rap album. The original idea was to shoot indiscriminately for a weekend, take that footage, cut it into minute- to 30-second long chunks, then upload all that to a YouTube channel and have each video titled, like, “JPEG.9864,” and have hundreds of these videos [forming] a loose narrative. But we sat on the footage for a long time, and Jack looked at it and was like, “I think there’s actually a good narrative here.” We wrote it into a movie, shot it very slowly.
Bensinger: We didn’t have fun making that short. We all felt bad about ourselves. We ate too much Doritos, felt like shit. So, we didn’t even look at the footage for a year, but then I chopped it up in a way that made us excited again.
Filmmaker: And why did you choose 2009 as the setting?
O’Malley: We wanted to talk about The Dark Knight. That was the main reason.
Scharar: If you watch the movie, The Dark Knight doesn’t even come up at all, but you can tell that these guys have seen it.
O’Malley: The original short was set in 2003, but we were referencing The Dark Knight a lot. So we were like, “Well, when we go back and shoot more, we’re gonna wanna reference The Dark Knight again.” We talked a lot about what year to set it in, and 2009 made sense because it’s closer to the time we’re in. But also I feel like there’s a 2000s type of guy—Loose Change, Immortal Technique guy—that just disappeared after 2009.
Bensinger: It was also the end of the Handycam, DV video era, right before DSLRs and phones, where you didn’t have to be proactively trying to be a filmmaker to get your hands on a consumer DV tape. It was this bastardized last wave of people who got their hands on consumer camcorders.
Filmmaker: What DV cams were you shooting on?
Scharar: We had three different cameras. A Canon GL2 A was the nicest one, and then [we had] progressively shittier cameras. I think only one survived by the end of the shoot, just because they’re not meant to be thrown around and shot in the freezing cold. Three cameras going was the goal.
Filmmaker: You shot this from 2020 all the way to 2024?
Scharar: We did the short version in 2020, and snippets of that are in the final movie, but very little. Then, winter of 2022, we started getting back into production and shot until summer 2023, finding weekends that worked for everyone’s schedule, because it was, like, everyone’s fifth job. Harris [Mayersohn], who produced the movie, described it as a YouTube video, until all of a sudden it got into a film festival and was a movie and now we’re taking it more seriously. It was very low stakes; now, it’s high stakes and serious.
Filmmaker: The primary location was an Airbnb in Tobyhanna, right?
Scharar: That’s right.
O’Malley: We looked around and that one looked good. It could sleep everybody.
Scharar: None of us are from Pennsylvania, but it felt like the right place to do it. Also, [it was like] an homage to CKY vibes. The visual aesthetic of that was definitely a big inspiration.
Filmmaker: Tobyhanna is that everywhere-and-nowhere place of strip malls and movie theaters. How close do you guys feel to those locations?
O’Malley: In terms of my own experience of childhood into early 20s, I was in Chicago, grew up in the city, but the vibe was the same—bored, no money or anything to do. Jack’s from the DC area, Eric’s from Seattle and Danny’s from Las Vegas. Everywhere that’s not New York or LA feels the same a little bit, with obvious exceptions.
Bensinger: When you have a strip mall, it doesn’t matter where you are in America. You feel the spirit of the global corporations that give this protective aura for people to come in and have life-changing experiences.
O’Malley: You see people living a full life in McDonalds. You can just park in a parking lot, chill, hotbox, listen to some music.
Filmmaker: There’s the line from the end of the movie: “Some of the best nights of my life were being had in parking lots.”
O’Malley: Now that I have responsibility in my life, if I eat something bad I feel like shit for the next two weeks, or if I don’t get enough sleep I feel completely fucked up. But when I was 19, I was like “Well, I’ll eat two bowls of cereal and go straight to bed at three in the morning, wake up at one.” And everything’s fine. There’s a period that this movie takes place in that most of these characters are about to exit.
Scharar: Now, if I was to text a friend and be like, “Hey, do you wanna go get McDonalds and hang out in the parking lot for two hours and pitch sketch ideas?,” they would say no. But if I said, “Wanna get a beer and get mildly drunk?,” they’d say yes. There’s something kind of pure about being like, “Let’s have french fries and talk about our dreams.”
Filmmaker: At the New/Next Q&A, you guys talked a little bit about how the movie was a document of your friends in New York before everyone dispersed and a lot of them moved out to LA. Was that an important part of the process in making Rap World, collecting those people together?
O’Malley: I would love to say, “Yes, this is a grand plan.” But it was also like, we’d have an idea for a scene and we’d be like, “Oh, what if I had a sister? It would be really funny if Edy [Modica] played the sister”—just asking people that were friends. Also, this comedy scene in New York had coalesced long enough and eventually hit a point where it’s like, “Are you gonna stay or are you gonna go out to LA?” It felt like everyone was gonna move to LA in 2020 or 2021, then COVID happened and everyone stayed. It afforded us this opportunity to make this movie. We made a lot of other work in this period.
Scharar: I feel like on the short, Conner, you explained it like that feeling you get making a sketch with friends during a sleepover: “What if we just did that now, but now we have all this experience about how to make things properly?” Then, when we made it, we broke every logistical rule of how you’re supposed to make something and didn’t do anything professionally. Sleepover vibes were definitely the north star.
O’Malley: It’s what I think streaming is now. Twitch streaming is like you’re hanging out with a person, but Bam [Margera] is genuinely an incredible filmmaker. That was another thing about CKY: you’re peering into this group of friends, and they’re so cool, driving Audis and having fun. [They’re] rich and still hang out in parking lots.
Filmmaker: I’m curious about how you built up your characters, because the costumes are so specific. I wonder if you create the character and then go for the costume, or if the costume influences the character in a way. I think that Jack’s Avenged Sevenfold shirt is so perfect; it adds so much to [his character] Casey.
Bensinger: We talked about the dynamic between the three of them, what’s their backstory, and went from there. We used an advanced mechanism known as Google Images to find similar styles and vibes. I think I already had the Avenged Sevenfold shirt. In the short I also had a Black Eyed Peas beanie, but we changed it [for the film] to have nothing on it. I would say characters came first. We thought about how Eric’s character was gonna be a photography person, so let’s get him up in the gray flannel v-neck.
Scharar: The stuff that Eric’s wearing, those were actually our producer Harris’ real clothes from high school. He went home and was like, “I’m stealing all this stuff.”
O’Malley: And Dan Licata gave me the “I go to N*SYNC concerts for the pussy” shirt.
Scharar: Ruby McCollister [who plays Keira] had such a good eye for fashion. She was sending links like, “I think my character should be wearing this specific shirt and this color lipstick.” It was fun to let everyone build out their character and the wardrobe with it.
Filmmaker: Is Rap World dropping on YouTube before the election?
O’Malley: Yeah, we’re putting it on YouTube soon. Literally every distributor doesn’t want to pick it up for political reasons.
Filmmaker: The version you were touring around at festivals is slightly different than the YouTube version.
Scharar: At the BAM [Brooklyn Academy of Music] screening, I looked over at Jack and he was in the back typing edit notes. So, it’s been a living movie that we tweaked and finessed, which is the nice part about touring it around. We’ve been able to get feedback and be like, “OK, this part really works, this scene we want to slightly tweak.” Jack was really the overseer of the edit and found the tone of the whole movie through the cut.
O’Malley: How many hours of footage did you watch?
Bensinger: It was 70 tapes. I think only two of them were broken. So I watched 68, probably.
O’Malley: And Jack really discovered, “What if they edit it themselves and are really bad at making movies?” He left in timeline mistakes and stuff.
Filmmaker: There’s a good audio cue when Eric’s getting the ring out [in the car] and, Conner, your line runs twice in that sequence. Also, the titles are so funny; it’s got the Windows Movie Maker vibe to it. I’m guessing you weren’t editing on Windows Movie Maker for practical reasons.
Bensinger: The visual style we’re going for is actually Final Cut Pro 6. It’s a very specific era.
O’Malley: What version is Final Cut on now?
Bensinger: It was over once they switched from Final Cut 7 to Final Cut X.
Scharar: Yeah, that shit sucked. It was like “We’re making iMovie Pro.” Get the fuck out of our face, we’re using Premiere now.
Bensinger: It’s like the Hummer switching to electric. It’s over.
Filmmaker: It’s funny, when I rewatched Rap World on a screener on my computer, the experience of watching it was so different seeing it in a crowd of people that are all cracking up. There’s a dread to it. It’s almost less funny, like I’m seeing something I shouldn’t be seeing.
Scharar: Yeah, you see people die on your computer all the time, but in the theater…
O’Malley: That is one thing I will say to Mr. Elon Musk: thank you for bringing back readily available murders and suicides on the computer that I can view first thing in the morning.
Scharar: And you don’t have to seek it out anymore. It just shows up for you, which is cool.
O’Malley: Curated for me, algorithmically.
Bensinger: Here’s what you can do, by the way, if you are watching it at home: have a little laugh track cue on the side, and just play that alongside with the viewing so that it feels like the way it felt in the screening.
O’Malley: I had an opposite feeling watching it screen: this is supposed to be watched on a laptop. That this is is being screened is weird. I’ve never really worked on a video or short film with the idea of it being played to a live audience or having the luxury of everyone in a theater not looking at their phone. Jack and Danny and Eric’s stuff is very similar—[we] had to make stuff that’s primarily viewed on laptops. That’s the fun of making stuff online: sometimes people start and they’re like, “Is this real? What is this?” There’s almost a dirty quality of watching porn or something on your laptop where it feels gross. But yeah, once we started to realize we would screen it, we started to tweak it a little bit.
Scharar: That’s something I think Jack really discovered in the edit, because this movie is being made for such a small budget, and the normal form of a movie doesn’t really matter to it. I remember seeing the first cut and there were scenes where you could feel Jack editing in character being like, “This is boring, let’s move on.” Which is what I think makes the movie special, but also makes it disorienting.
O’Malley: There’s this incredible luxury of an audience that is devoted and looking. We’ve been making stuff that’s like, “OK, am I gonna keep watching this, or am I gonna watch the Billions clip next to it, or ‘Margin Call scene?'”
Scharar: We will do a Subway Surfer release of the movie where it will be picture-in-picture.
Filmmaker: Did showing the movie to audiences change how you perceived your work?
Bensinger: Yes. When you think that you suck, and then you go and show people what you all have been working on and they really like it, it feels good. That was such a positive experience I didn’t know we would get out of making these YouTube videos from the beginning—when it felt like we all were just depressed and hated our performances and ate too much Doritos—to the other end of it, where we’re seeing it with all these people who are quite liking it. It made me feel happier.
O’Malley: It was a long process. We all met working on this pilot I had in 2019, [along with] Harris and Meryl [Faye Crock, Rap World’s other producer]. It was this FX sketch show called Content Guy that will never be released. I feel like Jack, Danny, Harris, Eric and myself all work together a lot, and have this experience of putting stuff out during the pandemic and it felt like you’re in a vacuum. Then we had this experience of going out and showing it to people and it’s like, “Oh, there’s actually people on the other side of this that are into it.” Everybody has jokes in the movie. Everybody did jobs beyond what they were not credited for. I feel so lucky to have this crew of people where we all were like, “Let’s invest in something for ourselves.”
Filmmaker: Was the whole thing self-funded piecemeal?
O’Malley: Pretty much every time [we shot] there was not an established [budget], but we had a number that was like, “If we’re approaching this, let me know and we’ll figure it out.” But we never even got close to it.
Filmmaker: DIY low-budget filmmaking.
O’Malley: That’s the only way to make anything now, I think.
Scharar: Slowly, over the course of four years.
Filmmaker: As far as the amateurishness goes for the filming, you can tell where Danny, you in character as Ben, think, “This is an amazing shot.” There’s a part after you guys get kicked out of the party where he zooms in on the headlights crossing the windshield, this very poetic moment set to “Free Fallin’.”
Scharar: There’s something to that Tumblr aesthetic of that time, like he knows something looks so overtly cool, but he doesn’t know how to cover two people talking. He’s just trying to whip back and forth as quickly as possible. But he can be like, “Oh, this looks like a desktop background.”
O’Malley: I think there is something about the model of that car that makes that shot really hit, just the angle of the windshield and the water in the headlights. That is the most 2009 shot in the whole movie, and that might just be the music and the car.
Filmmaker: What was the model of the car?
O’Malley: It was a ’99 Subaru Outback that our friend Johnny Frohman owned. He’s a DP and director. We rented it from him. It was really important to have a car from the 90s or early 2000s, even though there’s one shot that has a car from 2006. All of sudden we’re in a completely different model car. Nobody notices.
Scharar: And there’s a thing like, you watch a movie and they take out the headrests to make it easier for coverage—there was something really important to us about not making anything easier logistically or so it would look better, almost in a Dogme way. We didn’t have any film lights on set other than the green light that was in the room. Things are super dark.
O’Malley: That was for the rapping.
Scharar: Yeah, that’s a rap light, sort of a mood-setter. Shockingly, we have a colorist on this movie, just to match all three of the cameras. And that was an important note for us: when the camera is auto-adjusting to expose for a bright lamp in the background, don’t try to fight it at all. Let it crush images or blow stuff out. The more we leaned into it, the more real it felt. That’s the other thing—everyone at some point is grabbing a camera. Jack just came to us with a camera and was like, “Look what I shot,” and it was just the feet in the sink shot.
Filmmaker: I think it’s interesting that you guys felt like you were screaming into the void in 2020. That’s when I started paying attention to you guys, and I think a lot of film people, too. You were almost becoming a voice for that psychosis everyone was in–like, I just want to be screaming in a parking lot right now.
O’Malley: It was a weird time. It’s interesting that we’re still not really out of it production-wise. I feel like I worked more in the pandemic than I do now.
Scharar: That was the start of my real working relationship with Conner, outside of the pilot—I was the assistant for Jack, then during COVID I started editing for Conner’s YouTube. That was my only job, so we could take our time with videos and figure shit out, which I think is really helpful in finding my creative voice.
O’Malley: Just be able to sit on something for a couple weeks or months, and then be like, “Let’s try this”—I’ll look at old videos and just be like, “Fuck, cut this whole thing.” Before, it was like “Quick! Quick! Cut! Get it out!” You’d shoot and edit stuff in under a week, then the pandemic switched it. One video will be like three years or something. Why rush it?
Scharar: I was thinking about the cave video [FIX THE MARKET], Conner. There’s a line in there where you’re talking to the Orb and you say, “Make things chill again, like 2006 style.” And we were joking about feeling nostalgic in 2020 for the height of two wars right before a recession: “Make things like that again, please.” Rap World does have a little bit of nostalgia for when things were terrible.
