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Digable Planets Bring Jazz-Rap to Hulaween

Beyond jam bands, Hulaween festival brings a well-rounded lineup of stellar acts to Live Oak, including iconic trio Digable Planets.
Digable Planets Portrait Session backstage Neptune Theater, Seattle Washington August 9, 2019. L to R: Craig "Doodlebug" Irving, Mariana "Ladybug Mecca" Vieira and Ishmael "Butterfly" Butler
Digable Planets Left to Right: Craig "Doodlebug" Irving, Mariana "Ladybug Mecca" Vieira and Ishmael "Butterfly" Butler

Photo by Bruce Talamon

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Festivals like Ultra and III Points usually dominate Miami’s attention, but a road trip north lies a different world entirely. Since 2013, Hulaween has transformed the 800-acre Spirit of the Suwannee Music Park in Live Oak into a playground of music, art, and all-around good vibes. Hosted by jam legends the String Cheese Incident, the fest leans heavily on jam and EDM but has quietly built a streak of adventurous bookings beyond those genres. In past years, Anderson .Paak, Smino, and Thundercat have all touched down under the mossy canopy. This Halloween, Digable Planets keep the streak alive as Butterfly, Ladybug Mecca, and Doodlebug bring the jazz-rap cool that reshaped ’90s hip-hop to the North Florida wilderness.

For the uninitiated: Digable Planets’ debut album, Reachin’ (A New Refutation of Time and Space), dropped in 1993, carving out a unique space in the golden era of hip-hop. Where most rap crews leaned on booming drums and gritty samples, Digable Planets laced their rhymes with upright bass, horn lines, and a laidback swagger that owed as much to Miles Davis as it did to Rakim. In some ways, they were building on the path established by others who had been weaving jazz samples and Afrocentric ideas into rap since the late ’80s. But as founding member Ishmael “Butterfly” Butler puts it, Digable Planets were conscious of not simply imitating what came before. “I was heavily influenced by the people that I liked, Tribe Called Quest, the Native Tongues, N.W.A., Run-D.M.C., but you couldn’t really mimic too much, you had to separate yourself in some ways to gain notoriety,” he says. “I never thought it was going to have 30 years of staying power”.

But as it turns out, three decades later, their influence is undeniable. Since the group began touring again in the past year, Mecca shares how, “We may not always get to a particular favorite song for a fan. Sometimes I’ll hear about it in my DMs or on social media, not in a negative way, but more like a longing to hear it.” Songs from their catalog like “Rebirth of Slick (Cool Like Dat)” which earned them a Grammy, cemented their place as innovators and landed them lifelong supporters. Their follow-up, Blowout Comb, leaned deeper into Afrocentric politics and sprawling jazz-funk textures, gradually earning cult-classic status.

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After their second album, the trio parted ways, as happened with many groups from that mythical era, but they view it as a family dynamic. “There were many years where I didn’t think we’d ever get back together,” Butler says. “But with us it’s always been like family; you might not see each other for a while, but the bond is still there. To be traveling and performing again feels surreal, and I just feel lucky every time we hit the stage.” 

Wondering how they see themselves fitting into a lineup that doesn’t necessarily emphasize hip-hop, Butler puts it simply: “We’ve always been about blending worlds… jazz, poetry, politics, hip-hop, it was never about keeping things separate. A festival like Hulaween has the same energy. People come here open to whatever vibe you throw at them.” And that flexibility carries into their live shows throughout the tour. “We tweak it sometimes according to what’s going on,” he adds. “If it’s funkier or jazzier, we might throw some layers of that in there to speak to the vibe of the festival. The core remains the same, but it’s always evolving.”

Doodlebug agrees. “The Hulaween crowd should expect the unexpected,” he says with a laugh. “You’re not going to hear the album like you hear it at home. Each night has a different vibe, depending on the frequency we’re on. We might give it to you a little differently.” He continues, “Having the live band behind us just gives the music more depth. It lets us stretch out the songs, improvise, and make each show its own experience. It’s not the same as pressing play on a track.”

Picture of Hulaween Festival stage.
Past edition of Hulaween Festival

Photo by Aaron Bradley

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For Miami fans used to the neon chaos of Ultra or the art-club cool of III Points, Hulaween offers something else entirely. A six-hour drive north, the festival transforms the beloved wooded music park into a Halloween wonderland: costumed campers, world-class immersive art, and music that veers from jam bands to EDM to, increasingly, hip-hop. This year’s lineup also features Miami electro-pop duo Afrobeta and local psych-fusion outfit Anemoia, giving the fest an added hometown connection. The annual gathering has truly become a rare space in Florida where genres collide without hierarchy. Jam kids wander into hip-hop sets, ravers stumble into bluegrass jams, and nobody seems out of place. 

Digable Planets fits right into that ethos, giving attendees the chance to hear “Cool Like Dat” under a sky lit by lasers and Spanish moss instead of club strobes and velvet ropes. Hulaween isn’t about exclusivity; it’s about immersion and acceptance, and with Digable Planets on the bill, it’s about taking part in musical history, too.

Suwannee Hulaween 2025. Friday, October 31, through Sunday, November 2, at the Spirit of the Suwannee Music Park, 3076 95th Dr., Live Oak; hulaween.com. Tickets start at $169 (for 1 day General Admission) via hulaween.frontgatetickets.com.

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