Skippa’s Take on Trap-Dancehall Has Made Him a Star — and His Ambition Doesn’t Stop There: ‘I Want to Leave a Legacy’

With his slick delivery and penchant for true-to-life lyricism, 25-year-old Skippa from Kingston, Jamaica, set the tone for dancehall in 2026.

Skippa will take the stage at Billboard R&B Hip-Hop Live, Sept.

10 at Brooklyn Steel in New York City.

Get your tickets here .

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James and St.

Catherine parishes.

Blending the mainstream hip-hop influences of 50 Cent and Rick Ross with the gritty dancehall he heard outside of his childhood home, Skippa represents a newer trap-dancehall era that doesn’t balk at tempo.

The Breakthrough In December 2023, Latin Grammy-nominated producer Rvssian restricted access to his then-viral “Dutty Money” riddim, a roadblock for a musical culture that revolves around different artists hopping on the same production.

Skippa said, “F–k that beat,” and recorded “Self Belief,” which he dropped just 10 days before Christmas.

A somber trap-dancehall ballad built around murky piano, “Self Belief” found Skippa turning an obstacle into a career catalyst, collecting legions of new fans who felt seen by his ballsy play against dancehall gatekeepers.

By the end of 2025, his international breakthrough arrived: “WYFL,” a slick, sensual song he recorded over producers DJ MAC and CrashDummy’s steely, trap-infused riddim.

With over 5.8 million official on-demand U.S. streams, according to Luminate, “WYFL” became the first viral crossover riddim of 2026, attracting remixes from artists across genres including King of Dancehall Vybz Kartel, Bronx rapper Remy Ma and Trinidadian soca star Patrice Roberts.

“Me and Skippa [have] been working a while now,” DJ MAC told Billboard in March.