Sleepy Hallow dropped his debut album Still Sleep? earlier this summer, and fans got to hear more from the Winners Circle Entertainment collective led by Sheff G. Now, Sleepy is looking to lead the collective by issuing a special deluxe edition for his debut.

On Friday (October 8), the 2021 HipHopDX Rising Star unleashed Still Sleep? (Deluxe), keeping the energy from the first iteration alive. The deluxe edition comes with 11 new tracks as well as remixes to “Basketball Dreams,” “2 Sauce,” “Mi No Sabe” and more. Sleepy also threw in four music videos to the delight of his die-hard fans.

Still Sleep? debuted at No. 21 on the Billboard’s Top R&B/Hip Hop Albums chart and No. 38 on the Billboard 200. The second single off the album, “2055,” charted at No. 51 on the Hot 100, a large increase from his 2020 breakout single “Deep End Freestyle” featuring Fousheé going No. 80 on the same chart.

Sleepy Hallow has been on a mission carrying the Winner’s Circle banner on his back. His friend and labelmate Sheff G was arrested last July and charged with three counts of criminal possession of a weapon and two traffic violations. The fellow 2021 HipHopDX Rising Star was denied bail and remains locked up at the Otis Bantum Correctional Center in East Elmhurst, New York.

Before his arrest, Sheff G was going to join Sleepy Hallow at The Great New York State Fair last month. The two were being recognized for the fiery introductions into the rap game.

Sheff G & Sleepy Hallow's Rap Originality Praised After Huge Festival Look

Great State New York Fair Director Troy Waffner praised the Rising Stars’ talents saying, “Sheff G and Sleepy Hallow have an original style and this promises to be a great way for fans of hip hop and rap to wind up a summer of music.”

This month, fans will get the chance to see Sleepy Hallow hold it down for Sheff and the Winner’s Circle when he graces the stage at Rolling Loud NYC Day 3 with Travis Scott as the headliner for that evening.