Honestly, 1999 was a weird, golden fever dream for teen movies. You had the heavy hitters like 10 Things I Hate About You and She’s All That, but then there was this quirky, slightly more grounded entry originally titled Next to You until Britney Spears released a hit song and the studio pivoted for the marketing. We’re talking about the Drive Me Crazy actors—that specific ensemble that captured the late-90s "fake dating" trope before it became a tired meme. It’s been decades. Some of these faces became household names, while others basically vanished into the "Oh, that person!" category of character acting.
Melissa Joan Hart: The Queen of the TGIF Era
Nicole Maris was the quintessential popular girl with a heart of gold, played by the reigning queen of teen TV, Melissa Joan Hart. At the time, Hart was juggling this film alongside the massive success of Sabrina the Teenage Witch. It’s easy to forget how much power she held in the industry back then. She wasn't just an actress; she was a brand.
After the movie wrapped and Sabrina eventually ended its seven-season run in 2003, Hart didn't just fade away into child-star obscurity. She took a break, started a family, and then pulled off a rare feat: a second successful sitcom. Melissa & Joey, co-starring fellow 90s icon Joey Lawrence, ran for four seasons on ABC Family (now Freeform). These days, she’s become a staple of the holiday movie circuit. If you turn on a TV in December, there is a roughly 80% chance you will see her playing a bakery owner or a high-powered executive finding the "true meaning of Christmas." She also directed several episodes of The Goldbergs and the Young Sheldon spin-off, showing she’s got more staying power behind the camera than most people realize.
Adrian Grenier: Before the Entourage
Then we have Adrian Grenier. Before he was Vince Chase, he was Chase Hammond—the scruffy, "alternative" neighbor who needed a makeover to make an ex jealous. Grenier brought a certain indie-film moodiness to a movie that was otherwise very bright and poppy. It’s funny looking back because his character in the film is so anti-establishment, which is exactly the vibe he’s leaned into in his real life.
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Post-Drive Me Crazy, Grenier obviously hit the stratosphere with HBO’s Entourage. It defined an entire era of masculine wish-fulfillment television. But if you look at his Instagram now, you won't find him partying in Hollywood. He famously ditched the "Vince Chase" lifestyle for a farm in Austin, Texas. He’s heavily involved in environmental advocacy through his organization, Lonely Whale. He’s one of the few Drive Me Crazy actors who seems to have genuinely moved on from the industry's glitter, focusing instead on sustainable farming and ocean conservation. It’s a total 180. Honestly, his character Chase Hammond would probably approve of his current life more than his Hollywood years.
The Supporting Cast: Hidden Gems and Crossover Stars
The movie wasn’t just about the leads. The side characters were a wild mix of "who’s who" from the turn of the millennium.
- Stephen Collins: He played Mr. Maris. While he had a long career in shows like 7th Heaven, his legacy was severely tarnished later by serious personal controversies and legal admissions that effectively ended his career in the mid-2010s.
- Ali Larter: She played Dulcie. This was right around the time she was becoming the "it girl" after the whipped-cream bikini scene in Varsity Blues. Larter went on to be a massive genre star, leading the Final Destination franchise and starring as Niki Sanders in Heroes. She’s still very active, recently appearing in the procedural drama The Rookie.
- Adrian Chapman: He was the guy always trying to find the "perfect" girl. Chapman didn't stay in the spotlight like the others, eventually moving toward more niche roles and voice work.
Why Do We Still Care About These Actors?
Nostalgia is a hell of a drug. But specifically, the chemistry between the Drive Me Crazy actors worked because they felt like actual teenagers, not 30-year-olds in high school outfits—even if some of them were pushing their mid-20s. The film captured a transition point in cinema where the "alternative" kids and "preps" started to bleed into each other's worlds.
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The Director’s Vision: John Schultz
John Schultz directed the film, and he’s a name that pops up in a lot of cult favorites. He did Like Mike and The Honeymooners. His style in Drive Me Crazy was heavily influenced by the music video aesthetic of the time. Think about the pep rally scenes or the "Big Dance" finale. It feels like a three-minute Britney Spears video expanded into 90 minutes. This aesthetic is why the movie still gets traction on streaming services today—it’s a time capsule.
Missing in Action: The Ones Who Left the Spotlight
Not everyone wanted to stay in front of the camera. Keram Malicki-Sánchez, who played the eccentric Chris, has shifted heavily into the tech and VR space. He’s a big deal in the world of immersive storytelling now. It’s a common theme with this cast: they either became titans of TV or they left to do something radically different, like tech or farming.
There’s also the "Spears Factor." The movie is inextricably linked to Britney Spears because of the title change and her cameo in the music video that promoted the film. While she wasn't one of the Drive Me Crazy actors in the film itself, her presence looms over it. For a lot of fans, watching the movie is a way to revisit that specific 1999 cultural peak before things got complicated for the pop star.
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Fact-Checking the "Cult" Status
Is Drive Me Crazy a masterpiece? No. Even the most die-hard fans will tell you the plot is predictable. But it holds a 32% on Rotten Tomatoes for a reason—critics hated it, but audiences (especially those who grew up with it) gave it a much higher "Popcorn" score. It’s a comfort movie. When you track the careers of the cast, you see a snapshot of how the industry worked before social media. You had to have a "type," and you had to stick to it.
How to Revisit the Drive Me Crazy Legacy
If you’re looking to dive back into this world, don't just stop at the movie. To truly understand the impact of these actors and the era, you should look at the surrounding media.
- Watch the "Drive Me Crazy" Music Video: It features Melissa Joan Hart and Adrian Grenier in character, interacting with Britney Spears. It’s a weird meta-crossover that wouldn’t happen today.
- Follow the Indie Path: Check out Adrian Grenier’s documentary work, like Teenage Paparazzo. it gives a lot of context to his disillusionment with fame.
- Sitcom Binge: Watch an episode of Sabrina followed by an episode of Melissa & Joey to see the evolution of Hart’s comedic timing. She’s one of the few who mastered the multi-cam format over three different decades.
- Check the Credits: Look for Ali Larter in Heroes. Her range is actually pretty incredible when you compare her "mean girl" roots to her more dramatic, darker roles.
The Drive Me Crazy actors represent a specific moment in time when the teen rom-com was king. While Hollywood has moved on to superheroes and multiverses, these stars remind us of a time when the biggest stake in a movie was who was going to the prom with whom. Whether they are farming in Texas, directing sitcoms, or exploring virtual reality, they’ve all managed to outlive the "teen star" expiration date.