Brian Herzlinger had eleven hundred dollars. That was it. No Hollywood connections, no massive production studio backing him, and honestly, not much of a plan beyond a childhood crush on Drew Barrymore.
In 2005, the world got to see what happens when a guy with a Circuit City credit card and a dream tries to land a date with a literal A-list movie star. The result was My Date with Drew, a documentary that basically predicted the entire creator economy before YouTube even existed. It’s a weird, scrappy, and surprisingly emotional film that feels even more relevant today than it did twenty years ago.
The Impossible Math of a 30-Day Deadline
The premise was simple but terrifyingly high-stakes for a broke filmmaker. Brian won $1,100 on a game show and decided to spend every penny on a quest to get a date with Drew Barrymore. He gave himself 30 days. Why 30? Because that’s how long he could keep the video camera before he had to return it to Circuit City for a full refund.
That’s the kind of chaotic energy you don’t see in modern documentaries. Everything now is polished. Everything is color-graded to perfection. My Date with Drew looks like a home movie because, in many ways, it was. Brian and his friends—Jon Gunn and Brett Winn—were just trying to figure out how the industry worked from the outside looking in.
They didn't have publicists. They didn't have "ins." They had a Six Degrees of Kevin Bacon strategy. If they could just find someone who knew someone who knew Drew's assistant’s cousin, maybe they’d get a foot in the door. It’s an exercise in the "small world" theory that actually feels tangible. You feel the sweat. You feel the rejection. When they finally get a lead, you’re genuinely holding your breath because you know Brian's bank account is hovering at zero.
A Time Capsule of Pre-Social Media Fandom
Let’s talk about the year 2004/2005. No Instagram. No Twitter (X). No TikTok. If you wanted to talk to a celebrity, you couldn't just slide into their DMs or tag them in a viral video. You had to physically exist in the same spaces or navigate a labyrinth of gatekeepers.
The My Date with Drew movie captures a very specific moment in celebrity culture where the "wall" was still high. Drew Barrymore was (and is) a massive star, but back then, she was also somewhat elusive. Seeing Brian navigate the red tape of Hollywood is like watching a heist movie where the prize is just a dinner at a restaurant.
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It’s also a look at Drew herself. This was the era of Charlie's Angels and 50 First Dates. She was the "America's Sweetheart" of the 2000s. The film treats her with a level of genuine reverence that avoids being creepy—mostly because Brian is so self-deprecating. He knows he’s a dork. He knows this is a long shot. That self-awareness is what saves the movie from being a stalker manifesto and turns it into a charming underdog story.
Why the "Vibe" Shifted Documentary Filmmaking
Before this, documentaries were mostly serious. They were about social issues or historical events. Super Size Me had just come out a year prior, sparking a trend of "first-person" docs, but My Date with Drew was different. It wasn't trying to change the world. It was just trying to change one guy's Friday night.
The editing is frantic. It uses graphics that feel very "early internet." It’s loud. It’s fast. This style heavily influenced the way vloggers eventually structured their content. If you watch a "I Spent 24 Hours Doing X" video today, you’re seeing the DNA of Brian Herzlinger’s work. He proved that you could make a compelling feature-length film about a personal quest with almost no budget.
The "Drew" Effect and Celebrity Accessibility
What actually happens when you try to hunt down a celebrity? You realize they are surrounded by a fortress. Brian meets people like Corey Feldman, who gives him some surprisingly grounded advice about the industry. He talks to random people on the street. He calls every Barrymore in the phone book.
It highlights the sheer audacity of the human spirit. Most people would have quit on day three after the tenth "no." But Brian’s obsession—fueled by a childhood memory of seeing E.T.—is a powerful engine. There’s a scene where he’s just sitting in his apartment, looking at a cardboard cutout of Drew, and you realize he’s every fan who ever felt like they "knew" a star because they grew up watching them.
The film also tackles the reality of the industry. It’s not just about luck; it’s about persistence and who you know. The way Brian eventually maneuvers through the gauntlet of Flower Films (Drew’s production company) is a masterclass in "faking it 'til you make it."
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Is It Still Worth Watching?
Honestly? Yes. It’s a 90-minute shot of pure optimism. In a world where movies are often cynical or bloated with CGI, My Date with Drew is a reminder that people are fundamentally interesting.
The stakes are low in the grand scheme of things, but they feel like life and death for Brian. That’s the magic of the film. It makes you care about a guy you’ve never met getting a date with a woman who doesn't know he exists. It’s a testament to the power of the "Big Ask." If you never ask, the answer is always no.
There are some parts that haven't aged perfectly. Some of the humor is very 2005. Some of the editing choices feel a bit dated. But the core—the heart of the story—is timeless. It’s about the courage it takes to be embarrassing in pursuit of something you love.
Breaking Down the Production
- The Budget: $1,100 (plus some credit card debt, presumably).
- The Gear: A standard-def digital camcorder from a big-box store.
- The Strategy: Networking, cold calls, and sheer willpower.
- The Outcome: A theatrical release and a cult classic status.
Most people don't realize that the film actually won awards. It took home the Best Feature award at the HBO Aspen Comedy Arts Festival. It wasn't just a fluke; people in the industry recognized that Brian had captured lightning in a bottle. He turned a "nothing" story into a narrative arc with a beginning, middle, and a very satisfying end.
The Legacy of the My Date with Drew Movie
This film paved the way for the "everyman" creator. It showed that you didn't need a film degree from USC or a million dollars to tell a story that resonated. You just needed a hook.
When you look at the landscape of media now, everyone is trying to do what Brian did. We see people trying to get the attention of MrBeast or Taylor Swift through elaborate stunts. Brian was the pioneer. He did it without a platform. He did it without an algorithm to push his content. He just went out and did it.
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It also serves as a reminder of how much the "celebrity" has changed. Today, Drew Barrymore has her own talk show. She’s incredibly accessible. She’s on TikTok. She’s "one of us." In 2004, she was a distant star in a different galaxy. The My Date with Drew movie bridged that gap in a way that felt revolutionary at the time.
How to Apply the "Brian Herzlinger" Method Today
If you’re a creator, an entrepreneur, or just someone with a crazy goal, there are real lessons to be learned from this scrappy doc. It’s not about the money. It’s about the narrative.
- Set a Deadline. The 30-day limit was the best thing that happened to this project. It created urgency. Without the return policy on that camera, Brian might have spent three years making this and lost the momentum.
- Lean Into the Struggle. The best parts of the movie are when things go wrong. Don't hide the "messy" parts of your project. That's what people relate to.
- Use Your Network. You are probably three people away from anyone you want to meet. Start talking to people. Ask for the intro.
- Stay Vulnerable. Brian wasn't playing a character. He was a guy who was genuinely nervous and occasionally desperate. That authenticity is why people cheered for him.
The film ends, as it must, with a resolution to the quest. I won't spoil the final moments for those who haven't seen it, but it’s a masterclass in payoff. It satisfies the audience's curiosity while staying true to the documentary's grounded tone.
Final Takeaway
If you’re feeling stuck or like you need a "permission slip" to start a project, watch this movie. It’s proof that you can start exactly where you are with exactly what you have. You don't need a better camera. You don't need more followers. You just need to start the clock and see what happens in 30 days.
Next Steps for Future Creators:
- Audit your resources: Look at what you already own that can be used to tell a story. Brian used a credit card refund policy; what’s your "unfair advantage"?
- Define your "Drew": What is the one goal that seems impossible but would make an incredible story if you actually pulled it off?
- Commit to the "No": Expect to hear "no" a hundred times. If Brian had stopped at the first rejection, we wouldn't be talking about this movie two decades later.