Brooklyn, NY

JayBezzy

Jay Bezzy is the Heartbreak Kid from Brooklyn: a melodic rapper signed to Winners Circle Entertainment, the label built by Sheff G and Sleepy Hallow.

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Discography

Every drop, newest first

Use the links to hear the real thing.

Love Hurts by Jay Bezzy, cover art

Album · Sept 12, 2025

Love Hurts

Twelve songs, roughly thirty-six minutes, ending on the Fakish bonus with Sleepy Hallow. Heartbreak told in melody, with Sleepy Hallow on several records and Sheff G, Kaash Paige and TATA in the mix.

  1. Afraid Of The Dark
  2. Megan GoodSleepy Hallow & Sheff G
  3. Good Days
  4. I’ll Be ThereTATA
  5. 2 LateSleepy Hallow & Kaash Paige
  6. One Of A Kind
  7. Luv Me More
  8. New Year (Interlude)
  9. Sunday MorninSleepy Hallow
  10. Delirious
  11. Pretty & Special
  12. Fakish (Bonus)Sleepy Hallow

The run

From F**k Love to the next one

  1. c. 2017

    Starts recording

    By 2022 the label described him as five years into making music.

  2. 2021

    Signs to Winners Circle

    Announced with “F**k Love,” then “Overseas” with Sheff G and Sleepy Hallow, the two artists who founded the label.

  3. 2022

    Secrets, and From the Can

    A melodic single, and “Overseas” joins Sheff G’s From the Can as a bonus track.

  4. 2025

    Love Hurts

    The September album: 12 songs, with Sleepy Hallow on multiple records.

  5. 2026

    A run of releases

    D.T.F, X’s and O’s, How I Feel, Used To, DISTANCE. Five drops in five months.

  6. Next

    The album

    In progress. The countdown above starts when the date is set.

The circle

Who he runs with

Tap a name to see what they made together.

Fast facts

Bezzy, in brief

Who is Jay Bezzy?

Jay Bezzy is a melodic rapper from Brooklyn, New York, known as the Heartbreak Kid. He is signed to Winners Circle Entertainment, the label founded by Sheff G and Sleepy Hallow.

What label is Jay Bezzy signed to?

Winners Circle Entertainment. He signed in 2021 and his first release as part of the label was “F**k Love,” followed by “Overseas” with Sheff G and Sleepy Hallow.

What is Jay Bezzy’s latest release?

“DISTANCE” with Youngseason, a single released June 1, 2026.

When did Jay Bezzy release Love Hurts?

Love Hurts came out on September 12, 2025. It has 12 songs, runs about 36 minutes and features Sleepy Hallow, Sheff G, TATA and Kaash Paige.

When is Jay Bezzy’s next album coming out?

No release date has been announced yet. The album is in progress, and the countdown on this page starts when the date is set.

Who has Jay Bezzy worked with?

He has made records with Sleepy Hallow, Sheff G, Kaash Paige, TATA, Teddy Bushara, Youngseason and producer Great John. Sleepy Hallow appears on the most songs.

Business

Bookings & business