The Jones Awards 2025: A Night of Legacy, Laughter, and Royalty

Sep 9, 2025
2 min read

By Jenn Taylor

Chicago, IL — Theater Wit transformed into a palace of culture, comedy, and creativity on August 29th as The Jones Awards 2025 rolled out its red carpet. Once known as The Hollyhood Awards back in 2017, the rebranded ceremony has grown into a crown jewel for recognizing artists who embody excellence, resilience, and innovation.

This year’s edition delivered not only awards but unforgettable performances, laughter, and a deep reminder of why Chicago remains a cultural capital.

Honorees Spotlight

✨ Harold Dennis (above) – Miguel A. Núñez Jr. Legacy Presence Award

Harold Dennis, one of Chicago’s most respected independent film veterans, was honored for his decades of presence, perseverance, and consistency in uplifting indie film culture. His award symbolized more than career longevity—it recognized a spirit that refuses to fade.

🎶 Rob Diggy (above) – Bootsy Collins Funk & Innovation Award

When you talk about groove, soundscapes, and pushing boundaries in music production, Rob Diggy stands tall. His work has not only set the tone for films but also influenced a new generation of producers to bring funk and flair into storytelling.

😂 Maurice “Mo’” Jones (above) – Damon Williams Comedic Genius Award

Comedy is about timing, truth, and the ability to heal through laughter. Maurice “Mo’” Jones was celebrated for embodying all three, carrying the comedic torch forward with sharp wit and heart.

🎤 Sherell Brown (above) & Milon V. Parker (below) – MC Lyte Voice of a Generation Award

For the first time in Jones Awards history, this honor went to two recipients. Sherell Brown and Milon V. Parker were recognized for their powerful voices in entertainment and advocacy, shaping narratives that will echo for years to come.

🎬 Billy Ray Valentine (below) – Oscar Micheaux Film Legend Award

Carrying the name of the trailblazing Black filmmaker, this award saluted Billy Ray Valentine for a career built on vision, independence, and legacy in storytelling.

🏆 Anita Nicole Brown (below) – Audience Choice Award

With an overwhelming 83% of the vote, Anita Nicole Brown proved she’s not only admired but deeply loved by audiences. Her win demonstrated the power of connection between artist and community.

Performances That Moved the Crowd

Noble Bland (above) set the stage on fire with a sensual, R&B performance reminiscent of the golden “quiet storm” era, drawing comparisons to R. Kelly’s iconic vocal style.
Kala Ra (above) delivered conscious hip-hop bars that challenged the audience to think, reflect, and rise above.
Brother Benji (above) closed the performances with soulful tones that evoked the smooth, timeless energy of Al Green.

Each set reminded the audience that The Jones Awards are not just about trophies—they’re about live artistry that lingers in memory.

The Experience

Guests mingled over samples from Moor’s Beer, supporting Black-owned craft brewing, while savoring plates from De’ Le’ Crem’, the Black-owned food business run by Akilah Josephine Brown.