Sleepy Hallow & Annalise Azadian: The drill movement is reenergized with the WTW? Freestyle/First Day Out music video
I am always geeking out over those signature drill-inspired anthems. So it’s no shocker rap artist Sleepy Hallow coming through with his ‘WTW? Freestyle/First Day Out’ music video weeks after his release from behind bars? Yup - I am here for it.
Pure energy and real-life footage on display with crooner Annalise Azadian stepping up too? Completely tap in.
Sleepy Hallow used his recent time in prison to reflect on his responsibilities as a community leader and his mission as an artist, emerging with a new sense of purpose this past May. Today, the Multi-Platinum Brooklyn native makes his triumphant return to the rap scene, releasing "WTW? First Day Out," a two-pack EP via Winners Circle / RCA Records.
Each produced by frequent collaborator Great John, "WTW? Freestyle" and "First Day Out" encapsulate the rapper's state of mind as he regains his freedom. Rhyming with lilting melody over Great John's insistent percussion and descending synths, Sleepy speaks on loyalty and leadership on "WTW? Freestyle," expressing his desire to find comfort and love and praying for the serenity to accept the things he can't change. On the flip side, "First Day Out" is a celebratory anthem, with a hook from singer Annalise Azadian, as Sleepy describes his feelings of invulnerability and immense accomplishment amidst the new chapter in his career.Stream "WTW? First Day Out" HERE
The EP arrives with a music video, directed by Nimi Hendrix, featuring both songs presented back-to-back. Starting with clips of Sleepy making the most of this prison sentence, the video shows off the rapper's platinum plaques before he heads to Downtown Manhattan to meet the public upon his release from prison. The video for "WTW? First Day Out" drops at 3pm on Sleepy Hallow's YouTube channel.

