Sleepy Hallow Is Back and Claiming His Crown With “First Day Out” Featuring Annalise Azadian

The Brooklyn drill and melodic rap scene just got its heavyweight back. Sleepy Hallow is officially back in action, making his long-awaited return with a brand-new two-pack titled WTW? First Day Out, dropped via Winners Circle Entertainment and RCA Records.

Right at the center of the drop is the massive anthem “First Day Out” featuring the incredible vocals of Annalise Azadian.

A Fresh Chapter and a True Victory Lap

If you’ve been following Sleepy’s journey, you know this release means a whole lot more than just new music. Following a stint behind bars where he focused heavily on self-reflection, personal growth, and stepping up as a community voice, his return home feels monumental.

The two-pack pairs “First Day Out” with the Great John-produced “WTW? Freestyle.” While the freestyle leans into raw reflection, loyalty, and the heavy realities of being a leader, “First Day Out” is pure celebration.

Quick Facts:

• Artists: Sleepy Hallow feat. Annalise Azadian

• Producer: Great John

• Label: Winners Circle / RCA Records

• Vibe: Melodic Rap / New York Drill

That Annalise Azadian Touch

Let’s talk about the hook. Annalise Azadian absolutely floats on this track. Her smooth, soulful vocal delivery provides the perfect counterweight to Sleepy’s rugged, grounded cadence.

Behind the boards, Great John laces the track with crisp production that respects Sleepy’s New York roots while letting the emotion of the homecoming breathe. It’s that classic Winners Circle chemistry—effortless, hard-hitting, and built to echo through the city.

Cinematic Visuals by Nimi Hendrix

You can’t talk about this drop without checking the visuals. Directed by Nimi Hendrix, the back-to-back video gives you the raw, unfiltered truth of the transition.

It opens with real footage of the love and energy surrounding Sleepy’s release, flashes back to the journey, and quickly lands in Downtown Manhattan where he’s greeted by fans ready to celebrate his freedom. It’s powerful, authentic, and captures the exact weight of touching down and getting right back to work.

Stream WTW? First Day Out Now

Sleepy Hallow didn’t miss a beat. He’s focused, hungry, and ready to remind everybody why he’s one of the most important voices in modern rap.