Lester Rey

Lester Rey is a storyteller for a generation caught between worlds, caught in Liminality. Rooted in the rhythms of Puerto Rican folklore and the pulse of Chicago’s vibrant urban scene, Lester Rey weaves nostalgic tales of survival, the nuances of identity and self-actualization as a first generation diasporican. His music is a tribute to resilience, crafting a soundscape that is “ni de aquí, ni de allá”—a home for those who feel displaced yet deeply connected to their roots.

Blending salsa with shatta flows, reggaeton with boleros, and gritty club bass with Caribbean melodies, Lester Rey pushes boundaries, creating music that both honors tradition and embraces innovation. His voice—equal parts crooning, chanteo, and fearless experimentation—channels the complex realities of identity, love, and survival in a post-colonial matrix.

Lester Rey's ability to croon heartfelt lyrics while playing congas "con un sabor Caribeño” makes him a captivating performer. Since 2016, he has been invited to several festivals in Chicago, toured the nation, and has had his music shared by various outlets such as Remezcla, NPR, Chicago Reader, Vocalo and more! Lester Rey has shared the stage with many like minded contemporaries such as Chuwi, CimaFunk, Reyna Tropical, Residente (Calle 13), Ric Wilson, Cachorra, Nino Augustine, and many more. In 2017, the Puerto Rican Cultural Center gifted Lester Rey the key to Humboldt Park, a traditionally Puerto Rican neighborhood in Chicago.