Navv Greene joins Loon for a wide-ranging conversation on Hollywood, Black comedians in dresses, Katt Williams, Dave Chappelle, 85 South, Coming 2 America, Druski, Desi Banks and more. Navv Greene sits down with Loon on Its Up There for a wide-ranging conversation about Hollywood, Black comedy, Katt Williams, Dave Chappelle, 85 South, Coming 2 America, Druski, social-media money and what it really takes to survive in entertainment. The conversation gets especially interesting when Loon asks Navv a direct question: Would he ever wear a dress for a Hollywood comedy role? Navv says no. That opens a much larger conversation about the long-running debate surrounding Black male comedians portraying women on screen. Loon brings up Martin Lawrence, Jamie Foxx, Tyler Perry and others, while Navv explains how his perspective on those performances changed as he got older. The two also revisit Dave Chappelle's famous story about refusing a dress scene while working on Blue Streak. Chappelle publicly described refusing the proposed scene and said he was uncomfortable with what he viewed as a recurring pattern involving Black male comedians. But Navv also makes an important distinction: he says Hollywood has never personally approached him with anything strange like that. The conversation is about what he would do, what he's observed and why the larger issue continues to generate debate—not a claim that Navv was personally forced into anything. From there, Navv takes Loon behind the curtain of Coming 2 America. The conversation also gets into the rise of 85 South and what touring with DC Young Fly, Karlous Miller and Chico Bean did for Navv's career. Navv remembers walking onto the stage in Greensboro in front of roughly 13,000 people and learning how completely different comedy timing becomes in an arena. Loon and Navv then get into Katt Williams and the larger business of comedy. Navv pushes back on the idea that Katt was simply bitter during his viral interviews. What Navv says he took from Katt was the importance of being content with what you've built, while Loon takes the conversation further: what does “showing love” actually mean if successful comedians aren't helping each other build ownership and make money together? That leads directly into Country Wayne, Desi Banks, Funny Marco and social-media comedy. Navv explains why skit comedy is its own serious craft and why creators who understand Facebook, TikTok, playlists, engagement and repeat viewing have created enormous businesses that traditional stand-up comedians shouldn't ignore. They also discuss Druski, digital comedy ecosystems and what it would take for this generation to create its own Friday. And the episode goes well beyond comedy. Navv breaks down Broken Play, sports betting, PrizePicks, athletes dealing with angry bettors and why legalized gambling has changed the way fans watch games. Loon and Navv also get into relationships, social media, masculinity, therapy, success, sacrifice and what happens when internet conversations begin shaping expectations inside real households. This is a conversation about talent versus business, fame versus ownership, comedy versus Hollywood and what happens when Black entertainers finally start asking questions about the systems around them. Subscribe to It’s Up There for more long-form conversations with the people shaping entertainment, culture and business. #navvgreene #kattwilliams #85south 0:00 INTRO — Navv Greene Comes to It’s Up There 6:51 Navv Greene Auditions for Coming 2 America 8:28 Competing With Desi Banks & Atlanta’s Comedy Scene 9:09 How Hollywood Casting Really Works 15:05 Navv Finds Out He Got the Coming 2 America Role 17:54 Why Most of Navv’s Scenes Got Cut 19:08 85 South & Performing in Front of 13,000 People 21:57 How Black Comics Build Material Differently 26:16 Dave Chappelle, Kevin Hart & Protecting Jokes From the Internet 27:31 What 85 South Changed for Navv Greene 31:17 Broken Play & Navv’s Sports-Betting Habit 38:30 Why Sports Betting Changed How Fans Watch Games 39:42 Kyrie Irving, Kevin Durant & Bettors Blaming Players 43:18 Druski & Performing for a Completely Different Audience 44:29 Hollywood, Accents & Staying Authentic 45:52 Would Navv Greene Wear a Dress for Hollywood? 47:57 Why Don’t More Black Comedians Address It? 49:27 Dave Chappelle, Katt Williams & the Black-Comedian Dress Debate 53:16 The Chrisean Rock 20-v-1 Fight & Content Going Too Far 1:03:27 Why Creators Are Fighting Over Views 1:10:38 Why Navv Isn’t Fully Monetizing the Shift Leader 1:20:50 Kountry Wayne, Desi Banks & the Money in Social-Media Comedy 1:27:46 Katt Williams — Bitter or Finally Telling His Side? 1:29:17 Could This Generation Create Another Friday? 1:32:30 Druski, Digital Characters & the Future of Black Comedy 1:48:40 FINAL WORDS — Navv Greene & Loon