Ep. 104 - ChatGPT For The Win

Ep. 104 - ChatGPT For The Win

The Wolves are back — and this episode is loaded with basketball chaos, Indy hot takes, celebrity drama, and one of the wildest relationship scenarios we’ve ever debated. We kick things off with the New York Knicks winning the championship, and then dive straight into the Pacers’ tanking disaster that cost them a 2026 first‑round pick in a historically deep NBA draft. Pain. Real pain. From there, Starship Wes goes on a run about Indianapolis businesses, asking the question everyone’s thinking: Is everybody just winging it? Because from flyers to essays… it’s looking like ChatGPT is employed everywhere. Wes also talks about his feature in Buttered Magazine, and the Wolves break down the Sean Combs & Daphne Joy video leak — and yes, 50 Cent absolutely chimed in, because of course he did. Then we hit the big scenario of the week: You get a dream job overseas with life‑changing money, but your partner refuses to move. Do you go… or stay and risk resentment? Finally, the Wolves get petty about Indiana’s new wheel tax proposal to fix potholes — and Wes suggests an alternative that might make Eli Lilly cover their ears. Tap in for culture, comedy, controversy, and classic Wolves of Naptown energy.

Ep. 103 - Mafia Takeover II (feat. DJ Twist Money & DJ Jamaal)

The Midwest Mixtape Mafia is back in the building, and this time we’re joined by DJ Jamaal and DJ Twist Money for a wild, unfiltered, culture‑heavy conversation straight out of Naptown.DJ Jamaal breaks down how he got his start in the DJ world, following in the footsteps of Indiana DJ legends while carving out his own lane with a deep love for R&B music. He talks about the importance of diversifying your skill set, expanding your playlist, and being able to rock ANY crowd — weddings, clubs, corporate events, you name it.Twist Money and Jamaal also give us an inside look at their new mixtape series, where they’re putting some of Naptown’s hottest female rappers up against the industry’s best. They even dive into their R&B legends battle, creating a true versus‑style experience in the mix.We also take a moment to honor the late Tony Cleveland, discussing his impact on the city and the uncomfortable truth about people using his passing for social media clout. Is it really about clicks, or are some folks just hating from the sidelines while the city shows love?All this and more on another raw, real, and unfiltered episode of the Wolves of Naptown Podcast.

Ep. 102 - Breakups & Biopics

This episode is PACKED. The Wolves dive into the viral breakup chaos between Megan Thee Stallion & Klay Thompson and Cardi B & Stefon Diggs, and what these high‑profile splits say about modern relationships and public perception.Then we shift gears into the entertainment world as we break down the new Michael biopic — what we expected, what surprised us, and how it connects to past conversations we’ve had about Michael Jackson’s life, legacy, and choices.From there, we get into real‑life debates:• Is risking dangerous weather to go into the office “being a team player,” or is remote work the smarter move• Would you trade potential water contamination for jobs and higher property values — the real tension behind the Eagle Creek pipeline discussionAnd as a bonus:We actually went to see the Michael movie — and our full review is at the end of the episode.Tap in, drop your thoughts in the comments, and don’t forget to subscribe for more Wolves of Naptown conversations.

Ep. 101 - The Art Of Music (feat. Andrew Hunt)

The long‑awaited conversation with Andrew Hunt is finally here — and this episode is packed. The Wolves sit down with the multi‑talented creator, media mogul, and founder of Numbers Media Group to break down his journey through music, entertainment, and the evolution of his platform. Andrew also gives us an inside look at the Art in the Park Festival, his vision for Indianapolis creatives, and where he plans to take his brand next. Starship Wes and Andrew take a trip down memory lane, revisiting their high school days, early music grind, and the moments that shaped their creative paths. Meanwhile, Bosslady sparks a hilarious debate about why she thinks Township schools are “preppy schools,” and the crew does not let that slide. Then we dive into two major Wolves‑style scenario questions: “Your best friend confesses they committed a serious crime to protect their child and begs you to be their alibi. Are you lying for them or telling the truth?” and “If you became famous and your partner wanted to publicly display intimate pieces of your life in a museum, are you allowing it or protecting your privacy?” Tap in for real conversations, creative inspiration, Indy culture, and the classic Wolves of Naptown energy you already know.

Ep. 100 - Return Of Superman (feat. Terrell Woods)

The Wolves of Naptown celebrate a major milestone — 100 episodes — with the long‑awaited return of one of our original hosts, comedian Terrell Woods, a.k.a. Super Booker T. In this special episode, Terrell finally meets Boss Lady and opens up about life after leaving the show, including an unexpected health battle, a powerful comeback, and his renewed love for comedy and ComedySportz. He breaks down what it means to be a career comedian, reflects on being inducted into the ComedySportz Hall of Fame, and brings back the fan‑favorite segment he created: The Petty Segment. We also dive into a wild scenario: If your life was on the line and your partner had to perform “favors” on someone else to save you… would you appreciate the sacrifice or be disgusted by it? The Wolves don’t hold back. Thank you to everyone who has supported us over the years. Tap in on YouTube as we celebrate 100 episodes of culture, comedy, and Naptown storytelling.