WTW? First Day Out – Songs by Sleepy Hallow

BY Gabriel Bras Nevares Published on July 18, 2026

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Sleepy Hallow's "WTW? Freestyle" and "First Day Out" after his release from prison earlier this year over gang conspiracy charges.

Sleepy Hallow is one of New York City's biggest drill rappers, and he recently served a prison sentence on gang conspiracy charges. But he's out now, and celebrated his release by dropping the WTW? First Day Out two-pack with the "WTW?" freestyle and the Annalise-assisted "First Day Out" track. The first is a more low-key, melancholy, and cold take, with Hallow easing into his vocal delivery with composure and calm. On the other hand, the second is a more bouncy and high-energy drill cut with roaring guitars and Sleepy's trademark flows. For those who missed the Flatbush MC and want to get back into Brooklyn drill, these new tracks should satisfy.

Release Date: July 17, 2026

Genre: Hip-Hop

Album: N/A

Quotable Lyrics from First Day Out

I got chops in the crib, I ain't dying at home,
They don't like when I get in my zone,
I'm trying to gеt right, they keep saying I'm wrong,
Stop playing, girl, watch your tone

About The Author

Gabriel Bras Nevares

Gabriel Bras Nevares is a staff writer for HotNewHipHop. He joined HNHH while completing his B.A. in Journalism & Mass Communication at The George Washington University in the summer of 2022. Born and raised in San Juan, Puerto Rico, Gabriel treasures the crossover between his native reggaetón and hip-hop news coverage, such as his review for Bad Bunny’s hometown concert in 2024. But more specifically, he digs for the deeper side of hip-hop conversations, whether that’s the “death” of the genre in 2023, the lyrical and parasocial intricacies of the Kendrick Lamar and Drake battle, or the many moving parts of the Young Thug and YSL RICO case. Beyond engaging and breaking news coverage, Gabriel makes the most out of his concert obsessions, reviewing and recapping festivals like Rolling Loud Miami and Camp Flog Gnaw. He’s also developed a strong editorial voice through album reviews, think-pieces, and interviews with some of the genre’s brightest upstarts and most enduring obscured gems like Homeboy Sandman, Bktherula, Bas, and Devin Malik.