Matt Zingler Built Rolling Loud From The Underground Up

But music festivals have shape-shifted over the decades, going from an accessible and economical way to see acts both new and old in one space to a luxury experience. The inaugural Woodstock in 1969 was $18 for a weekend ($120 in 2026), and the first Lollapalooza only raised prices slightly to about $30 in 1991. Zingler and Cherif noticed the rising costs for fans and artists alike, and ultimately decided to go back to their humble roots for Rolling Loud’s tenth iteration by lowering ticket costs and moving the festival from Miami, which doesn’t have the proper infrastructure to host an event of this magnitude, to Orlando. It’s fitting, with Zingler remarking that the festival is akin to Disney World for underground rap fans.

Now, in 2026, Rolling Loud has become a behemoth in the festival space, striking the balance between the mainstream and underground. I remember my first Rolling Loud in 2019, witnessing Juice WRLD months before his untimely death, a young and spry NBA YoungBoy performing mid-day to a thousand people, a developing Megan Thee Stallion, and even a fresh-faced DMX. Over the years, some of the scene’s biggest stars and most promising acts came and went, sometimes by luck, other times by incarceration or violence. Despite being banned from performing from the festival’s New York iteration in 2019 by former mayor Eric Adams, Pop Smoke was able to perform at Rolling Loud Los Angeles months before his death. Committed to championing young acts even in the face of unfair stigma, Rolling Loud is going back to their roots. Low prices. One city. One goal: to get back to the music.

Read full PAPER’s interview with Zingler below.

What inspired the move to Orlando after being intertwined with Miami for so long?

We’ve been talking about shifting to Orlando now for two years.The inflation in Miami has been very aggressive, and it’s been tough for fans. Once everybody knew Miami was happening, everybody kind of took advantage, including airlines. Orlando has such a massive amount of hotels and the flights are cheaper, so it made a lot of sense for us.

Camping World Stadium is close to downtown, too, so it’s walkable. You don’t need any public transportation anymore, so it cuts out the issues with Ubers. We also felt ticket pricing should come down, so we did tickets starting at 249 this year. It made sense for today’s times.

It’s refreshing to hear this approach. For many, Rolling Loud was their first festival and they always find a way to come back, or this year will be their first.

It's been interesting to see the shifts over time. Our fans are now a little bit older, right? We started our festival in 2015, so it's been 10 years. Some of our fans might be in their mid 30s, it's just a little bit different from what their taste of music might be or what they're looking for. The actual fan demographic of Rolling Loud has never really shifted. The hyper focus has always been what's hot and very underground-centric. You see music on Tiktok and Twitter and kids uploading their own stuff on SoundCloud again. You have artists that can become superstars overnight, right?

As our festival ages, it's still timeless, and that's been a big thing for me. I don't want to keep doing the same thing every year. It got a little repetitive in hip hop music and you started seeing similar faces on all the bills, and we really wanted to switch it up this year. The overall site experience is always going to be amazing. It’s what you'd expect from Rolling Loud, which is the biggest hip-hop festival in the world.

You have an impressive headliner bill with Don Toliver, Playboi Carti and NBA YoungBoy. Aside from the obvious, what went into those decisions?

I've always been a massive supporter of Carti, specifically the cultural relevance behind him. It's very different than what you're seeing a lot of other talent. He's just kind of mysterious and more iconic than a lot of talent is right now at a headliner level. It doesn't work for everybody. We call it aura, right? He's a superstar.

NBA YoungBoy, you know, coming from performing at Rolling Loud in 2019, his incarceration, and the explosion of his music, he’s one of the most-streamed artists! His numbers are insane.

For Don Toliver, I believe it's time he’s a headliner. He's been proving himself repeatedly, and I think ultimately, he's great. He's consistently brought out really large talent for the show. He brought out Justin Bieber for one of our events. He's done so much in this space. I think all the headliners selected are relevant and the right choice for the current time.

There’s also a very heavy UK presence this year which reflects how big their underground scene has become in the US.

You haven't really seen UK music convert domestically for a long time. Central Cee completed a crossover into mainstream, but you haven't really seen the underground cross super aggressively. With the viability of talent and new ways to digest music like Tiktok and other platforms, it's just so readily available that when Fakemink caught some kind of unique niche, it became like, Oh, wow. These guys are using certain beats that really sound unique and can be digested in his own world. You're seeing the resurgence of an aggressive underground UK scene and it’s actually converting. You see Esdeekid doing shows domestically and Fakemink. These artists aren’t getting big looks on festivals. It’s a rare booking. If fans don't know who they are, time to educate yourself. You’re going to see them live, so dive in. This is just what's hot right now. That Timothee Chalamet comparison was huge for Esdee’s career. These guys are getting cosigned left and right.

There’s also an increased presence of women rappers. My first time seeing people like Megan Thee Stallion and Ice Spice was at Rolling Loud!

Hip-hop music has always been a male-dominated genre, and it's been difficult for women to excel at that level, so providing them a stage and a platform has always been important to us as a brand. We want to shed light on their accomplishments without sacrificing the underground focus. A lot of these female artists become almost like pop stars, right? Doja Cat, Megan, even Latto are just so big now, some of it doesn't fit. We're definitely focused on elevating the young and hot talentn and we always reach out to an abundance of female talent, just to be like, hey, what do you got going on? What do you want to do? A lot of the names on the bill are developing female talent, which is super exciting to me.

Tiacorine, Karrahboo, Jorjiana, CLIP, Molly Santana, Trim. There's just a ton of stuff on there that people will really enjoy. Hip-hop's always been male-dominant, so of course, people are going to always see kind of more males than females. But we got to shed light on the women doing their thing. It's important.

Going back to Rolling Loud trimming down from three shows to one stateside show, what was it like pulling back?

Everything's about timing, and the brand's been around for 10 years. If you look back, 2015, 2016 was one show, and then we grew to the West, right, and then we expanded with more demand quite drastically like New York, Toronto, San Francisco. We did some international shows here and there. At that time, hip-hop music was just exploding and there was so much fresh talent. As time went on, it just became more accessible for these artists with touring and performing in arenas. The bigger thing was the adjustment in music that informed our decision to focus on one show. Let's make it the hip-hop Super Bowl. Let's make it the one event of the year that you can't miss, and bring all our fans together and really create the most boutique experience domestically, and then focus on international. We have Sydney, Melbourne coming up. We're gonna be doing India again this year, and a few other markets internationally, and providing this unique experience all over the world. It's important to me to also bring talent that have never been to these places. It's exciting to see how it converts. And for the brand, we're very focused on lifestyle brands, so we're focused on the merchandising and the movie that's coming out with Owen Wilson and Matt Rife, which is going to be huge. That's going to be in 2500 theaters. The lifestyle of Rolling is what really makes it special, and the history. You can’t repeat history, especially with what we’ve been able to accomplish.

You have the Pelle Pelle collab!

It’s super dope. I'm a big fan of Pelle. I always have been. We have certain collabs coming out this year that are bucket list for me from when I was younger that I would rock. Some are relevant now and some might not be as relevant, but are culturally impactful. Pelle was a great collab. It's very limited. There's around 100 pieces. It's just something I've always wanted to do. I think in general, specialty items are important for lifestyle brands. It’s part of the culture and community that we've created.

Hip-hop has been almost consistently one of the most popular, profitable genres but has only recently been catered to on the festival front. How do you feel about that as one of the earliest champions of some of these stars?

When we first started, I would say that a lot of talent weren't given the opportunity to tour, to play arenas or anything. There wasn't much interest in that. It was considered a liability, and a lot of festivals turned away from booking “urban talent.” I mean, look at Coachella! There’s barely any hip-hop this year. They could say it's not relevant or they might just not want to book that genre of music. But I think what we did was we took the chance because we knew it was what people were listening to. We were able to provide a community of like-minded individuals who love music and it was a recipe for success. Sometimes when you go to a restaurant, you want a specific food. You don't always want a conglomerate of Greek and Italian.

If you made a playlist, it's everything you want on the playlist. If you're a fan of Carti and YoungBoy and Don Toliver, what else do you have on your playlist? Because, unfortunately, I can't trust Rap Caviar on Spotify, because it's all tailored and paid or created by something else that's not a person. Now we're here. You're never going to get those iconic sets. You're never going to get those viral moments. You're never going to get Uzi jumping off a tower from front of house. You're never going to get all these artists to perform at the same place at one time, because if you were there, there was nothing like it.

What’s one Rolling Loud moment that made you realize you had something special?

It was our first show. I've never done an event that had so many artists on one day. During the conception of Rolling Loud, when I decided to add all these talents on one day, I always thought about how they would commingle with one another or if they'd come out together. There's a video on YouTube of 2015 Rolling Loud. It was stage two. Travis Scott headlined that stage. At the time, he wasn't as big. Post Malone was there too, but he was way smaller at the time too. He had just dropped “White Iverson” and it had very low streams. He came to the show. I didn't really know who he was at the time, but he was friends with somebody and we got him up on stage, and he just didn't leave. So it was like Travis Scott, XXXTentacion and Post Malone, like all these huge superstars on the stage. There was probably like, I don't know, 800 people there? That's when I knew this is something special, where you can bring artists together. They can meet each other at the shows. They can elaborate on projects they want to do, connect or reconnect with fans.

How do you balance the superstars with the upcoming artists?

It's a two-part answer. I think Rolling Loud has proven itself to deliver consistently for our fans. If you look back on all of our lineups, you're gonna get a shit ton of talent for a great price. If you broke down what it would cost you to see Playboi Carti, YoungBoy and Don Toliver, you're gonna be looking at $350, $400 each. And then on top of that, you have a shit ton of talent that's going and playing House of Blues for $40 or $50. Then you have a bunch of undercards that are playing really cool, eclectic rooms, 500 capacity and you’re paying $30. So you're really getting over $1000 worth of talent starting at $249.

We always deliver because we’re tapped in. We’re constantly combing through the internet, looking at music, looking at their fan engagement. Osamason has insane fan engagement. He's a very young artist. He just blew out his whole US tour run. It’s really interesting, because it's sometimes one or the other, right? Some might have streams, but they don't have the fan engagement. We don't really just look at one thing. What's the combined value here and who really wants to see you? Maybe they wouldn’t go out of their way to see you on a Tuesday night and spend $40, but shit, if you're at Rolling Loud, they’ll catch you. That's how we stay tapped in.

What is your message for fans, whether this be their first Rolling Loud or their tenth?

That’s also a two-parter. They’re two different fans. I’d tell the OG fan that times are changing, music is different, and it’s exciting. Be open-minded. It’s going to be incredible. You’re going to get the Disney World of hip-hop, so just enjoy and check out new music.

For the new fan, hydrate. Don’t get too excited too fast. Get food in your system. Make sure you get in the merch lines early because we always sell out. Build a schedule with your friends so that you are in a group, because it’s more fun that way. Lock your in hotels early and buy your flights now. Be safe, and get ready.

photography dani case
story jade gomez

chief creative officer brian calle
executive creative director jordan bradfield
senior editor joan summers