In a time when misinformation moves faster than truth and algorithms often dictate what we see, the role of the cultural commentator has never been more essential. From Instagram Lives to podcasts, newsletters to neighborhood conversations, these voices do more than just report — they translate what’s happening in our world through the lens of Black and Brown Chicago.
This list celebrates 25 individuals who have become trusted sources, storytellers, and cultural translators. Whether through entertainment, music, education, or community conversations, they use their platforms to inform, uplift, and hold power accountable — all while keeping Chicago’s soul at the center.
While names like Bree Specific and Cody McKee were intentionally excluded to avoid bias — along with anyone directly connected to WHATS THE WORD programming — this ranking was curated internally by the WTW team to spotlight the people who continue to define the pulse of the city, both locally and beyond.
At a moment when America’s cultural temperature feels uncertain, these are the commentators that the people turn to for clarity, context, and connection. They represent the best of what it means to be of the culture — rooted in truth, powered by purpose, and unmistakably Chicago.
A cultural commentator analyzes and provides commentary on society’s ideas, customs, and arts through media platforms like journalism, television, and online outlets. They observe and interpret cultural trends, social issues, and creative works, often using platforms to provoke thought, highlight inequality, and encourage critical thinking. Cultural commentators may have diverse backgrounds, such as academia or art criticism, and work across various mediums, including traditional news, specialized journals, and social media.
Honorable Mentions: DJ L, Money Maha, Donnell Writes, Bo Deal, DJ U TV
25. TRENCHES NEWS
24. BRANDON POPE
23. GARTATIA
22. Amon Phillips & Abasi Thompson
The Corner Convo Podcast stands among Chicagos hardest working podcast ever, blending unapologetic sports conversation, comedy, and community insight that captures the city’s real voice. The show has amassed over 12 million views on YouTube and millions more across Instagram and TikTok, drawing engagement from NBA icons like Shaquille O’Neal, Kevin Durant, Isiah Thomas, and a slew of others. Breaking into Spotify’s Top 50 Society & Culture podcasts, peaking at #34, The Corner Convo has also toured nationally with “The New Rory & Mal” podcast, ranked Top 15 by Complex, while averaging 7–10K plays per episode across platforms. Rooted in culture, comedy, and conversation — this is Chicago, unfiltered.
Amon Phillips Bio
Amon Phillips is the creator of The Corner Convo Podcast, a culture-driven show spotlighting Chicago’s influence across sports, music, and community. He also produces What’s Funny Today — a comedy-business podcast with Knowledge and Lil Rel Howery — and co-hosts SportzUnplugged with Chicago legend Leon Rogers. Amon’s work with national talents like Bill Bellamy and Mark Aguirre showcases his expertise in production, storytelling, and strategy, cementing him as one of Chicago’s leading voices in modern podcasting.
Abasi Thompson Bio
Abasi is a former All-City Chicago hooper who helped lead Indiana State University to its first NCAA Tournament since Larry Bird and later took his talents overseas. Now a 20-year veteran law enforcement officer, he brings sharp insight and unapologetic honesty to every topic. A proud father and co-founder of Camrin’s H.O.P.E. for Achievement, Abasi is also known as the internet’s new #1 hater — and the bold, unfiltered host of The Corner Convo Podcast, Chicago’s #1 culture and conversation platform.
21. RO$$ MAC
BIO: Hailing from the South Side of Chicago, Ross Mac is an Ivy League graduate who has dedicated his life to democratizing access to financial education. As a former Wall Street professional for Morgan Stanley and Grosvenor Capital, Ross empowers urban communities through his financial literacy media company, Maconomics. Maconomics is a Telly Award winning digital content series that blends education and entertainment to share insights on the world of finance. Ross is a media personality who works with Yahoo Finance, BET, Revolt TV, and Complex. He’s recognized as a McDonald’s Game Changer, enabling him to provide financial education to the nation’s top high school athletes that play in the McDonald’s All American game. Most recently, he brought financial freedom to millions of people around the world with his latest Netflix Documentary called “Get Smart With Money.”
He has been featured in Forbes, Bloomberg, CNBC, Yahoo Finance, ABC, Black Enterprise, and more.
20. JOJO ALONSO
19. TAY CAPONE
18. DREA O
17. TERRY ROSELAND & JONES
BIO: Roses Are Dead is a Chicago-born podcast hosted by Terry Roseland and Jones. Each week, they cut through hand-me-down myths about manhood, relationships, and community with straight talk, research-backed insight, and lived experience. The show centers accountability, emotional range, discipline, purpose, and practical growth—no performative chivalry, no clout chasing. Expect real stories, smart debates, and audience call-ins, plus Patreon exclusives (daily/bonus monologues, community chats, and shadow-work prompts). Rose’s Idea is where men sharpen men—and where everyone listening leaves with tools, not just takes.
16. LARRY LEGEND
BIO: Comedian, Writer, Chicago Cultural Griot
Brands: Larryislegend, Smoked Out Saturdaze, Culture Cellar
Bio: Larry Legend is a creative force shaping how Chicago’s stories are told. Through comedy, writing and cultural commentary, he documents the city’s people, places and pulse, blending humor with history to preserve its legacy and push its culture forward.
15. LUL B
14. MATHEW ALVAREZ
13. 16SHOTEM VISUALZ
12. TONE, KEKE, ZACH
11. MALIK KIZIR ZAMBEZI
BIO: Malik Kizir Zambezi is a Chicago-based photographer and creative director whose work captures culture, emotion, and identity through a cinematic lens. Deeply rooted in Chicago’s creative community, he founded @chiartchives to highlight and connect local artists. Malik also created The Black Metropolis Project, a Juneteenth photo series honoring Bronzeville’s rich history and cultural legacy. His work blends visual storytelling with purpose—using art as a bridge between inspiration, community, and legacy.
10. JA’MAL GREEN
09. DOMETI PONGO
08. KB NENE
07. VIC MENSA
06. SHERMAN “DILLA” THOMAS
BIO: Hailing from the South Side of Chicago, Ross Mac is an Ivy League graduate who has dedicated his life to democratizing access to financial education. As a former Wall Street professional for Morgan Stanley and Grosvenor Capital, Ross empowers urban communities through his financial literacy media company, Maconomics. Maconomics is a Telly Award winning digital content series that blends education and entertainment to share insights on the world of finance. Ross is a media personality who works with Yahoo Finance, BET, Revolt TV, and Complex. He’s recognized as a McDonald’s Game Changer, enabling him to provide financial education to the nation’s top high school athletes that play in the McDonald’s All American game. Most recently, he brought financial freedom to millions of people around the world with his latest Netflix Documentary called “Get Smart With Money.”
He has been featured in Forbes, Bloomberg, CNBC, Yahoo Finance, ABC, Black Enterprise, and more.
05. SAMANTHA CHATMAN
BIO: Samantha Chatman is a 2x Emmy-Award winning Anchor and Investigative Reporter for Chicago’s #1 news station, ABC 7 Chicago. Samantha is also the host of her own talk show, Mama, I Made It! Samantha’s journalistic background affords her the opportunity to share captivating stories from people of all walks of life. Her passions include helping Chicagoans from underserved communities and sharing inspirational conversations from people who turned their pain and misfortune into purpose and power. Her new talk show is getting rave reviews from people across the country. She has interviewed guests like Tina Knowles, Common, Tamron Hall and Chance The Rapper to name a few. She was recently recognized in Crain’s Chicago’s 40 Under 40 Class of 2025.
Samantha is from the South Side, a proud member of Alpha Kappa Alpha and The Links, Incorporated. She serves on the associated board for After School Matters and the National Association of Black Journalist as scholarship chair. She’s also a children’s book author.
04. FYB JMANE
03. THE TRIIBE CHICAGO
The TRiiBE launched in 2017 to “reshape the narrative of Black Chicago in pursuit of truth and liberation.” It’s commitment to cultural coverage comes out of a deep appreciation of Black publications like Ebony and Vibe magazines and the desire to continue that lineage. The TRiiBE has also been a voice of Black radical politics and roots its work in liberation traditions. At the same time, their cultural coverage aims to uplift the beauty, resilience and rawness of Black creative expression.
Since its launch, the award-winning publication has remained Black-owned and operated, supported by community memberships and philanthropy. The TRiiBE is nationally recognized as a newsroom that is redefining journalism for the digital age.
The Triibe provides a platform for some of the cities’ dope commentators, such as Rome J, Corli Jay, Mark P. BraBoy, plus More!
02. THE JAAM PODCAST
01. YOUNG WILL
