Let’s be real for a second. By the time The Steve Harvey Show season 5 rolled around in the fall of 2000, the landscape of the WB was shifting. It’s weird to think about now, but back then, Steve Hightower was the glue holding that network's Friday night together. You had the high-top fade, the flashy suits, and that signature "Regina!" shout that basically defined a specific era of Black sitcom excellence. But season 5 was different. It felt heavier.
The show was peaking, yet it was also starting to show the cracks that happen when a sitcom starts outgrowing its own premise.
Most people remember the laughs. They remember Cedric the Entertainer—playing the legendary Cedric Robinson—stealing every single scene with a gym whistle and a dream. But if you actually sit down and rewatch The Steve Harvey Show season 5, you notice something. The stakes changed. We weren't just watching a former funk star teach music to rowdy kids anymore. We were watching a group of characters realize that the "high school" phase of their lives was ending, both literally and figuratively.
The Romeo and Bullethead Problem
Look at the kids. Or, well, the "kids." By 2000, Merlin Santana and William Lee Scott weren't exactly looking like high schoolers anymore. Romeo Santana was the heartthrob, the guy every girl in the 2000s had a poster of, but in season 5, the writers had to get creative. How long can you keep these guys in a classroom before it feels like Grease, where everyone looks thirty?
They leaned into it.
The chemistry between Romeo and Bullethead in The Steve Harvey Show season 5 is arguably the best in the series. They had this shorthand. This rhythm. You’ve got episodes like "The Honeymooners," where the duo tries to navigate the complexities of adulthood while still being stuck in the hallways of Booker T. Washington High. It was funny, sure. But it was also a little sad because you knew the clock was ticking.
Regina and Steve: The Long Game
Honestly, the "will they, won't they" trope usually dies a painful death by season three. Most shows mess it up. They either wait too long and the audience stops caring, or they pair them up and the tension vanishes.
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The Steve Harvey Show season 5 handled the Steve and Regina (Wendy Raquel Robinson) dynamic with a surprising amount of grace. By this point, Regina Grier wasn't just the principal; she was the foil to Steve’s ego. Their relationship in this season felt more grounded. They were dealing with actual adult problems—career shifts, jealousy that didn't feel like a plot device, and the looming reality of what happens when your work life and personal life become a blur.
There’s a specific energy in the episodes where Steve has to reconcile his past as a member of "Steve Hightower and the High-Tops" with his present. He’s a mentor now. In season 5, that transition feels complete. He’s no longer the guy just looking for a paycheck until his next hit record; he actually cares about those kids. Even the annoying ones.
Why Season 5 Felt Different Internally
Behind the scenes, things were moving. Steve Harvey was becoming a massive star outside of the sitcom world. The Original Kings of Comedy had already happened. He was doing radio. He was doing stand-up specials that were breaking records.
You can see that confidence on screen.
In The Steve Harvey Show season 5, Steve’s comedic timing is surgical. He doesn't have to try as hard. He can just give a "look" to the camera, and the audience loses it. But that success also meant the show was becoming a smaller part of his empire. There was a sense that everyone involved knew they were nearing the finish line. The WB was also pivoting toward shows like Smallville and Gilmore Girls. The "urban" sitcom block that had been the network's foundation was being phased out.
It’s a pattern we see a lot in television history. A show builds a network, the network gets successful, and then the network "rebrands" away from the very audience that put them on the map. Season 5 was the last full, robust breath of that original WB spirit.
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Key Episodes That Defined The Season
If you’re going back to watch, there are a few moments that really stand out.
- "Player, Interrupted": This episode hits that perfect balance of Steve’s ego and the reality of aging. It’s classic Harvey.
- "The Great Pretender": This is where the ensemble really shines. It wasn't just the Steve and Cedric show anymore; the supporting cast was carrying heavy loads.
- The Lovita Alizay Jenkins Factor: Can we talk about Terri J. Vaughn? Because she was the secret weapon. Her character, Lovita, could have been a caricature. Instead, her relationship with Cedric became the most stable, hilarious, and heartwarming part of the show. In season 5, their dynamic is peak comedy.
The Cultural Weight of the 2000-2001 Run
We don’t talk enough about the fashion. The Steve Harvey Show season 5 is a time capsule of Y2K Black excellence. The oversized suits? Check. The leather jackets? Check. The specific transition from 90s grit to the shiny, polished look of the early 2000s is visible in every frame.
It also represented a specific type of mentorship.
Think about it. How many shows today feature a Black male lead in a position of authority who is allowed to be flawed, funny, and deeply invested in his community? Steve Hightower wasn't perfect. He was vain. He was often selfish. But he was there. In a television era that often leaned into stereotypes, this show—especially in its later years—offered a version of Black middle-class life that felt lived-in.
The Technical Shift
The production value in The Steve Harvey Show season 5 saw a noticeable bump. The lighting was warmer. The sets felt less like "soundstages" and more like actual locations. Stan Lathan’s direction throughout the series remained consistent, but you can feel a certain slickness in the 22 episodes of this season.
They were playing to a live studio audience that was clearly obsessed with the cast. You can hear it in the cheers. When Cedric walks on screen in a particularly loud outfit, the applause isn't canned. That’s real love. That energy translated through the screen and is why the show remains a staple in syndication decades later.
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What Most People Get Wrong
People often lump the final two seasons together. They think the show just "ended." But there’s a massive difference between season 5 and the shortened season 6.
Season 5 was the last time the show felt like it had its full wingspan. They were doing full-arc storytelling. They were exploring Regina’s ambitions and Steve’s fears of irrelevance. By the time they hit the end of this run, the writing was on the wall, but the quality hadn't dipped. Usually, by year five, sitcoms are recycling plots about long-lost twins or "it was all a dream" sequences. This show stayed in its lane.
The Legacy of the High-Tops
Ultimately, The Steve Harvey Show season 5 served as the bridge to Steve Harvey's next act. It proved he could carry a brand for over 100 episodes. It solidified Cedric the Entertainer as a household name.
It’s easy to dismiss multi-cam sitcoms as "old fashioned" now. We like our comedies dark, single-camera, and without a laugh track. But there is a craft to what they did in season 5. To keep a live audience engaged, to hit those punchlines while maintaining a shred of emotional honesty—that’s hard.
The show wrapped its fifth season in May 2001. A few months later, the world changed. TV changed. The WB changed. But for those 22 episodes, we had a perfect slice of what Black sitcoms could be: loud, proud, and genuinely funny.
How to Revisit the Series Properly
If you're looking to dive back into this specific era, don't just hunt for clips on social media. The context of the full episodes matters.
- Watch the background characters: The students in Steve’s class often had running gags that only pay off if you watch the season chronologically.
- Pay attention to the musical guests: The show was a massive platform for R&B and hip-hop acts of the time.
- Check the credits: Look at the writers and producers who got their start here and went on to run some of the biggest shows on TV today.
To get the most out of your rewatch, start with the season 5 premiere " "Wall to Wall Counseling" and pay attention to how much more "adult" the humor feels compared to season one. It’s a masterclass in how a show matures alongside its audience without losing its core identity.
The best way to experience it now is through streaming services like Tubi or Pluto TV, which often carry the full library. Turn off your phone, ignore the "modern" pacing of today's 30-minute comedies, and just let the rhythm of Steve and Ced do the work. You'll see exactly why this season stands as a landmark in sitcom history.