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Hillman Rewind

Ray "DJ Diggy" Andrews & Nichole Ross
13 episodes   Last Updated: May 15, 25

Hillman Rewind is your backstage pass to the culture, lessons, and legacy of A Different World. Hosted by HBCU alums Ray (DJ Diggy) and Nichole—who both walked the same campus where the iconic show was filmed—we take a nostalgic yet engaging look at every episode, bringing the laughs, the memories, and real talk about why this show still matters today.

As 80s babies raised on A Different World, we’re bringing our personal experiences, Black college pride, and cultural insight to every discussion. From Ron’s antics to Whitley’s evolution, from Dwayne and Freddie’s academic grind to the real-world issues the show tackled, we’re unpacking it all. Whether you’ve been rocking with Hillman since day one or just now stepping on campus, this is your space to celebrate and critique one of the most impactful shows in Black television history.

So pull up, press play, and join us as we rewind back to Hillman!

Episodes

Episode 12: Morris Brown CollegeTitle: Counseling, Crises & Cutting CornersIn this episode of Hillman Rewind, Nichole and DJ Diggy dive into the chaos of campus life when good intentions collide with finals pressure. Denise takes on a peer counseling role to dodge her own academic responsibilities—and it backfires fast. From juggling emotional labor to avoiding the inevitable, this episode brings all the lessons.We unpack college study habits, boundaries, and the unspoken rules of campus beauty standards—yes, we’re talking about the scarf moment. Plus, we reflect on how we support others without losing ourselves, and how real growth means facing what we’re running from.🎓 Hillman Homework:Have you ever taken on more than you could handle to avoid something else? Or—did someone ever comment on how you looked when you were just trying to survive finals week? → Drop your story in the comments or tag us using #HillmanHomework!
Episode 11: Florida A&M UniversityTitle: Flirtation Flip: When the Game Gets Reversed This week, we dive into a rarely explored angle—what happens when a woman makes the first move, and the guy isn’t into it? Dwayne gets unexpectedly pursued by classmate Peggy, and instead of honesty, he leans on a lie to escape the situation. Denise steps in to defend his right to have boundaries, and we talk all about emotional consent, reversed gender roles, and why honesty (with grace) still matters. We also explore dating older women, personal space, and what sisterhood looks like when your friend is in an uncomfortable spot.🔁 We’re flipping the script—because vulnerability and boundaries aren’t just for one gender.🎓 Hillman Homework: Have you ever had to turn someone down—or been turned down—and what did you learn from that experience? Or, tell us about a time you or a friend caught feelings for someone older. We want to hear your stories!👉 Use #HillmanHomework and tag us in your post or comment to be featured in next week’s episode!
Episode 10: Stillman CollegeTitle: Family, Gifts, and Grown-Up ShiftsThis week on Hillman Rewind, Nichole and DJ Diggy dive into the grown-up moments that college doesn’t quite prepare you for— what it means to see our parents as full humans, not just caretakers — and the emotional maturity required when life hits differently. we’re unpacking how college forces us to grow up—emotionally, socially, and personally.We talk adulting with parents, learning how to accept things you don’t agree with, and finding joy in unexpected friendships. Plus, we drop a few college-friendly gift exchange ideas to keep the spirit light.🎓 Hillman Homework: When did it first hit you that your parents were just people, trying to figure things out too? Or… what’s the most thoughtful, funny, or cringeworthy college gift you ever gave (or got)?→ Share your story in the comments or tag us on IG using #HillmanHomework—we just might read it on the next episode!
Episode 9: Hampton UniversityTitle: Crush Culture, Dorm Doors & Dream ChasingIn this episode of Hillman Rewind, Nikki Nich and DJ Diggy explore the complications of admiration and attraction when Denise and other students catch feelings for their geology professor. We talk boundaries — from the emotional kind to literal dorm room doors — and reflect on how important personal space is during college life.We also dive into Stevie’s storyline about not dating for years, opening up conversations about putting dreams on hold and the courage it takes to chase them again.🎓 Hillman Homework: Tell us: What was one unspoken rule about personal space you had in college? Or drop your funniest (or cringiest) crush moment from campus life. Use #HillmanHomework!
Episode 8: Paul QuinnTitle: "Track Star Triumphs & Trials"In this episode, we explore A Different World Season 1, Episode 8, where Denise joins the track team and struggles to keep up. We dive into what it means to step outside your comfort zone, balance academics with extracurriculars, and manage the pressure to prove yourself.💼 Hillman Homework: What’s something new you tried in school that surprised you? Was it a win, a lesson, or a little bit of both? Share your story in the comments! 👟
Episode 7: Morehouse CollegeTitle: Homecoming Hustle & HeartIt’s homecoming at Hillman! In this episode, we break down A Different World Season 1, Episode 7, where Denise’s grandpa pays a visit, and the students steal the rival school’s mascot head. We’re diving into the excitement of homecoming traditions, the wisdom our elders share, and the impact of family legacies—both inspiring and overwhelming. Plus, we reflect on those unexpected expectations that can throw us off course but ultimately shape who we become.💼 Hillman Homework: What’s your favorite homecoming tradition, or how has a family legacy or unexpected expectation shaped your journey? Drop your stories in the comments! 👇
Episode 6: Bennett CollegeTitle: Little Siblings, Big InfluenceIn this episode, we’re diving into A Different World Season 1, Episode 6, where Rudy visits Denise at Hillman but ends up spending the weekend shadowing Whitley instead! We explore the dynamics of sibling relationships, the power of mentorship, and how popular students can shape campus life.From funny sibling visit stories to memorable mentors who made an impact, this episode is full of nostalgia and real-life connections.💼 Hillman Homework: Tell us about a sibling visit that went sideways—or share the name of someone you really looked up to on campus.Drop your stories in the comments!
Episode 5: Benedict CollegeTitle: That’s DebatableThis week on Hillman Rewind, we’re stepping into the debate ring and tackling one of the hottest topics from A Different World Season 1, Episode 5—should women work or stay home? Back in the 80s, this was a major discussion on college campuses, and we’re breaking down how the conversation has evolved over the years.Join Nichole and Ray as they compare college debates then vs. now, discuss shifting gender roles, and reflect on how social media has changed the way we engage in discourse. Plus, we’re sharing personal stories about heated college debates, campus discourse, and the importance of critical thinking in higher ed.💡 Hillman Homework: What’s a debate or discussion from your college days that really stuck with you? Was it in class, in the dorm, or just a late-night cafeteria argument? Drop it in the comments or share with us using #HillmanHomework!Press play, rewind back to Hillman, and let’s talk it out! 🎧🔥
Episode 4: Tennessee State University Title: Lessons, Lies & Late NightsClass is in session! In this episode of Hillman Rewind, we’re diving into A Different World Season 1, Episode 4, where tutoring sessions, gossip, and late-night conversations take center stage. Ray and Nichole break down the academic hustle, sharing their own experiences with tutoring—both giving and receiving help—and the best strategies to stay on top of your studies.But college isn’t just about hitting the books; it’s also about navigating the social scene. We’re unpacking the world of campus rumors, how quickly they spread, and the wildest ones we've ever heard. Plus, how did A Different World handle gossip, and what lessons can we take from it today?🎓 Hillman Homework: What’s the wildest rumor you ever heard (or maybe even started) on your campus? Drop it in the comments or tag us on social media with #HillmanHomework!Tune in, press play, and let’s rewind back to Hillman! 🎧🔥
Episode 03 - Southern A&M UniversityTitle: Rules, Romance & Retro Style – Life at HillmanSummary: The dorms had rules, the organizations shaped us, the crushes were real, and the fashion? Unforgettable. This week on Hillman Rewind, we’re talking about dorm monitors and those college rules that kept us in (or out of) trouble, the importance of student organizations, the excitement of first campus crushes, and a look back at 80s college fashion compared to today’s trends.Plus, we’ve got this week’s Hillman Homework—we want to know what was a rule that your dorm had that you thought was stupid when you were in school? Drop your answers in the comments or tag us on social media with #HillmanHomework and join the conversation!Press play and let’s rewind back to Hillman!