Sleepy Hallow and Sheff G, Brooklyn’s best rap duo, may have both grown up in Flatbush, may be known to wear matching Puma sweatsuits, and may have both dropped Great John-produced 2019 solo mixtapes that feel like an extension of each other—but they aren’t the same rapper. Sheff G, with his thunderous voice that sounds like a bowling ball hitting the ground, is the technician. On his May mixtape, One and Only, there’s not a pocket he can’t catch or a verse he doesn’t rap with life-or-death intensity. Sleepy Hallow is not as fine-tuned, on his new solo mixtape, Sleepy for President, whether he’s reflecting on his trauma and paranoia or puffing out his chest, he spits with the kind ease and flash that starts block parties.
Listen to Sleepy Hallow’s early 2020 single “Deep End Freestyle,” and it’s straightforward: a single verse, no hook, the beat a simple looped vocal sample. But the song, clocking in at under two minutes, is perfect for endless replays, and has become the viral soundtrack for TikTok dance videos, a treasure chest of New York quotables (“My body different”) and the biggest Brooklyn drill song not made by Pop Smoke. Sleepy Hallow shines when he keeps it minimal like this.
The Brooklyn-raised twenty something has a refreshing style. Like Polo G—though not nearly as melancholy or polished—he blends the rushed cadence of traditional drill rapping with a rugged singing voice. On the gloomy “Anxiety Freestyle” he delivers his bars with an appealing looseness that makes pain sound like a good time: “Pop a perc now I’m back to life.” On “All In,” he tackles a flip of Weldon Irvine’s “Morning Sunrise” that has been done better before—Just Blaze’s iconic “Dear Summer” beat comes to mind—but his vocals are sharp and infectious. On the introspective “Bad Luck,” Sleepy smoothly delivers evergreen reflections about living in fear of death, “Demons at my door say ‘they just wanna come inside’/Shots fired, opps shot, another opp died/Cops shot another black guy”—lyrics that resonate harder than usual as the current wave of protests against police brutality continue.
But Sleepy’s sound is so bare that one misstep derails the entire track. Typically it’s because of New Jersey producer Great John, whose acoustic guitar-sampling beats—“6 AM in NY” and “Bankrolls”—lack the country soul of similar production behind Deep South singing rappers like Rod Wave and Rylo Rodriguez. Sleepy’s forced duets with Fivio Foreign and Jay Critch, pale in comparison to the tape’s three collaborations with Sheff G. The duo complement each other perfectly: their seamless back-and-forth “Water” and “Molly” should be spilling out of Flatbush car windows in no time. Then, there’s “Don’t Panic,” which follows in the fiery and relentless footsteps of the four previous songs in their “Panic” series—each Brooklyn drill essentials in their own right. Right now it’s clear that what needs to happen is the inevitable Sleepy Hallow and Sheff G joint mixtape. But until then, *Sleepy f
