Sleepy Hallow revisits his chart-topping album, Still Sleep?, with the release of a searing deluxe version

As far as drill goes, Sleepy Hallow is taking the genre into his own hands. While the NYC-native rose to prominence in 2019 off the back of a series of hard-hitting, grit-edged singles, 2021 saw a change in tack. Still Sleep? is minimalist and effortlessly light, while somehow never straying from the drill proclivities he’s made a name for himself with. 

It might be because drill has taken a backseat over the last few years when it comes to the scene, or maybe Sleepy Hallow just feels like injecting a little sunshine into his sound. Whatever the cause, it worked – and he’s just dropped an expanded deluxe version of the album, with a whopping 25 tracks to fill out the corners of your hip-hop afternoon. 

He might be working the underground NYC  scene hard, but South Africa is among the Top 5 regions in the world where he’s really made an impact. If you’re not familiar with the driving, heady verses of his latest emo rap single “2055” – which is nearly Gold in South Africa – do yourself a favour and change that. 

Still Sleep? is also a cheeky jab at those who might not have been paying attention to his, and his personal label Winners Circle Entertainment’s, global rise through the ranks. And it seems to have done the trick. 

Spotify has named him their next RADAR artist – which highlights emerging global stars and will feature them on a mini-documentary dropping later this year. Chart-topper “2055” just became RIAA-certified Platinum, and he’s been selected as one of HipHopDX Rising Stars 2021 and BET Amplified Artist of the Month (back in January). Not bad for a kid off the NYC underground block. 

Sleepy Hallow channels a self-professed loner-meets-street sound: a minimalist, bass heavy, clear-cut selection of verses delivered with even-keeled aplomb. He waxes lyrical on the basics mostly – tough childhood leads to searing ambition, women (“Luv Em All” is all about the free love), money, sex, drugs, more ambition, and a touch of mental health crises (“Gloomy Conscious”). But the generic themes are coupled with a sprawling, laid-back quality to the production that see him standing firmly on two feet. 

He’s softer than usual but something about the simplicity this time around works oh-so-well. Don’t sleep on this guy, he’s here for the long haul.