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Winners Circle Entertainment

@winnerscirclebk

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Artists: @sheff_g , @_sleepyhallow_ , @officialjaybezzy_ @greatjohnmusic
🛒: @winnerscirclestore

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@harbornewyorkcity

#winnerscircle
#freesheff by @winnerscirclebk

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23 days ago

Jail Stream by @winnerscirclebk

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2 months ago

Jail Stream by @winnerscirclebk

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(FUNKFLEX DAILY NEW MUSIC) WHAT NEW MUSIC AM I MISSING?
@_sleepyhallow_

THIS SONG IS SUPER CRANKING! by @winnerscirclebk

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After months of anticipation, the Brooklyn drill pioneer just dropped his new album “Weight On Me”, packed with 16 tracks and features from G Herbo, Skrilla, Wallie The Sensei, and Sleepy Hallow. The project has been one of New York’s most talked-about releases, with fans waiting to hear Sheff’s next full body of work after everything he’s been through.

The video in this post is for “Ventilator” featuring G Herbo, one of the standout collaborations on the album. The track brings together two of drill’s biggest names and has already been getting early praise from fans.

With records like “Ventilator,” “Woke Up” featuring Sleepy Hallow, and “Cashing Out” featuring Skrilla, Sheff is looking to remind everyone why he helped shape New York Hip-Hop.

What’s the hardest song on Weight On Me so far? 👀🔥

#raprelevant #sheffg #gherbo #nydrill #newmusic taken in New York by @winnerscirclebk

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3 months ago

Sleepy Hallow showed up to CPNYC and we had a blast!

The scholars were treated to lots of giveaways, food, basketball, and of course, good music. Our CEO, Ms.Sharon Content, read a message from Sheff G to the scholars, and Sleepy also shared a few words of wisdom.

Thank you Sleepy (@_sleepyhallow_) and Sheff G (@sheff_g) for showing up, having fun and making an impact on our lives this Summer.

Remember you can also show CPNYC some love by donating to their It’s Giving Summer Campaign or following us on Instagram.

@winnerscirclebk
@_coachroc
@bk_net_work
@overtimerozy
@kviews27 by @winnerscirclebk

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3 months ago

Summer Jam 2026.

Shot by @whatwouldpetedo
Edit @upstategroove

#freesheff
#sleepyhallow
#winnerscircleent by @winnerscirclebk

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3 months ago

Fightland Premiere

🎬 @whatwouldpetedo
Edit @upstategroove

#Freesheff
#Fightland
#winnerscircleent by @winnerscirclebk

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3 months ago

@_sleepyhallow_ at @50cent “FightLand” premier in NYC!

#fightland by @winnerscirclebk

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3 months ago

@_sleepyhallow_ "Wtw? / First Day Out" Out Now
#newmusic #reels #explore

Director @nimihendrix 🎥
Edited by @upstategroove 🎨 by @winnerscirclebk

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3 months ago

WTW/FDO OUT NOW‼️

Director @nimihendrix

Prod @greatjohnmusic

Video link in bio.

#sleepyhallow
#winnerscircleent
#freesheff by @winnerscirclebk

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3 months ago

Gramercy Theatre📍

#winnerscircleent
#paymeskrilla
#sleepyhallow by @winnerscirclebk

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