Top 10 Commentary YouTubers From Chicago

Chicago has long been known for its bold opinions, sharp humor, and unapologetic honesty, qualities that translate perfectly into the world of online commentary. From social issues and internet culture to pop culture takedowns and thoughtful long-form analysis, Chicago-based commentary YouTubers have carved out a unique space on the platform.

Their Midwestern perspective often blends grounded realism with biting wit, making their content resonate strongly with a U.S. audience that values authenticity over polish. Below is a detailed look at ten standout commentary YouTubers from Chicago who have built loyal audiences by saying what many people are thinking – just more clearly or courageously.

1. Danny Gonzalez

Danny Gonzalez is one of the most recognizable commentary creators to come out of Chicago. Known for his energetic delivery and sharp comedic timing, Gonzalez built his audience by dissecting cringeworthy internet trends, low-effort content, and bizarre corners of YouTube culture.

What sets him apart is his ability to balance humor with genuine critique, never punching down but always punching up at lazy or exploitative content.

His Chicago roots often come through in his dry sarcasm and straightforward delivery, making his videos feel both entertaining and grounded.

2. Drew Gooden

Often mentioned alongside Danny Gonzalez due to their collaborations and similar origins, Drew Gooden is another Chicago-based commentary YouTuber who excels at thoughtful humor.

His content leans more analytical, often breaking down marketing scams, viral trends, or cultural oddities with a calm, methodical tone. Gooden’s strength lies in his writing; his scripts are tightly constructed, allowing jokes and insights to land with precision.

3. Kurtis Conner

Kurtis Conner may be Canadian by birth, but his rise as a commentary YouTuber is closely tied to Chicago, where he spent significant time building his platform and collaborating with other creators.

His content focuses heavily on internet culture, outdated television shows, and social commentary, often infused with progressive viewpoints.

Conner’s delivery is fast-paced and expressive, reflecting the kind of confidence that thrives in a city known for outspoken personalities.

4. Eddy Burback

Eddy Burback brings a slightly different flavor to Chicago’s commentary scene by blending travel, consumer culture critique, and observational humor

. Many of his videos explore the absurdities of American businesses, abandoned malls, or questionable corporate practices. His commentary feels particularly relevant to a U.S. audience because it often focuses on everyday experiences most Americans recognize.

5. Jarvis Johnson

Jarvis Johnson is known for his introspective approach to commentary, often diving into topics like influencer culture, social media algorithms, and online misinformation.

Based in Chicago for much of his content creation journey, Johnson brings a tech-savvy and socially aware perspective to his videos. He doesn’t just mock bad content; he explains why it exists and how it impacts audiences.

6. Chad Chad

Chad Chad has quickly become a standout voice in the commentary space, and her Chicago ties play a role in her confident, straightforward presentation.

Her videos often critique questionable behavior, internet personalities, and viral trends with a mix of humor and moral clarity.

What makes her content compelling is her refusal to overcomplicate issues; she calls out nonsense plainly while still offering thoughtful context.

7. Scott Cramer

Scott Cramer is another Chicago-area creator who blends nostalgia with commentary. His videos frequently explore old commercials, outdated media, and forgotten trends, using them as a lens to comment on how American culture has changed.

Cramer’s tone is softer and more reflective than many commentary YouTubers, but his insights are no less sharp. His Chicago background contributes to his relatable, everyday-guy persona, which helps his commentary feel accessible rather than judgmental.

8. Nickisnotgreen

Nickisnotgreen represents a newer generation of commentary YouTubers who approach internet drama and cultural issues with a more personal, conversational tone.

With roots in Chicago’s creative scene, his content often reflects a balance between critique and empathy. He tends to focus on accountability rather than mockery, which sets him apart in a genre often dominated by sarcasm.

For U.S. audiences interested in commentary that feels socially aware without being preachy, Nickisnotgreen offers a refreshing perspective.

9. Pinely

Pinely has gained attention for his clean editing style and focused critiques of online trends and personalities. While less flashy than some larger commentary channels, his Chicago-based perspective shines through in his straightforward approach.

He prioritizes clarity and evidence over exaggerated reactions, making his videos feel more like thoughtful discussions than rants. This measured style appeals to viewers who want commentary that respects their intelligence and time.

10. Big Joel

Big Joel rounds out the list as one of the more intellectually driven commentary YouTubers associated with Chicago. His content often dives into media analysis, religious themes, and cultural narratives, offering long-form critiques that challenge viewers to think deeper.

While his videos may not follow traditional commentary formats, they exemplify Chicago’s tradition of critical thought and bold discussion. For a U.S. audience interested in commentary that goes beyond surface-level takes, Big Joel provides a unique and valuable voice.

Their success proves that strong opinions, when delivered with authenticity and intelligence, can travel far beyond city limits.