That Time I Made a Site for Entourage

And Jeremy Piven Ruined the Project

Still from Entourage, Jeremy Piven, HBO.

Years ago, while doing web consulting, I found a niche as the guy agencies would bring in when a project went utterly sideways. Most of the time, I felt like a firefighter in the middle of a dumpster fire with no way to put it out. Back in 2006, I was doing contract work for Deep Focus, a Brooklyn-based agency in Dumbo by that famous spot everyone takes a picture of the Manhattan Bridge. 

Back then, Dumbo was still “up and coming” and Deep Focus was mostly a Flash banner shop. Right around the time I started, they were trying to get into interactive websites - one of my specialties. I was only there for a few months, helping out on several projects, but one of my more memorable ones was for HBO’s Entourage.

Photo credit: Caroline Culler via Wikimedia cc

Thanks to a serendipitous introduction, I became a fan of Entourage. Back when I worked for the Jets, the head of legal, Hymie Elhai —who’s now the president— gave me the DVD box set of the first season because I had never seen it before. I binge-watched it, and a few months later, I found myself working on a project for the show. It’s just another one of those weird flukes where I worked on something related to a famous person or show I love. This was the first of several projects I worked on for HBO over the years, but those are war stories for another time.

Deep Focus had me work on a project called "Interview with Ari." The idea was to create an online interview with Ari Gold, Jeremy Piven’s character in the show. Back then, video conferencing was still in its infancy, and Skype was the major player in town. The concept behind the site was to do a virtual interview where Ari would ask you questions, and users could type in responses, all while watching dynamic video replies. When your interview was over, you’d get an email letting you know if you “got the job.” Spoiler alert: you never did because he always hated you. 

Sounds cool, right? This not-so-original idea was inspired by Burger King’s Subservient Chicken site, a little webcam of a guy in a chicken suit you could ask to do things by typing in messages under the video feed. 

The agency had pitched an ambitious project to HBO with no straight-forward way to build it, and since I was just a consultant, they ironically never consulted me during the pitch, so when they got the green light, no one knew how to pull this off. I had just finished two projects for them, the first being a microsite for a terrible Fox movie no one remembers, and the other called “pimp my profile” for MySpace as part of a marketing campaign for Date Movie. I did technical direction on a shoot with Tony Cox, cut up all the video, and built the site, which is how I got pulled into this Interview with Ari project. 

Still from Pimp MyProfie, Tony Cox, Date Movie.

This was my bread and butter—jumping into these chaotic situations and figuring out how to make things work. My role again was technical lead and developer. I was tasked with not only figuring out how to build the engine for the site and video editing, but how to tie everything together seamlessly. But Subservient Chicken set a high bar to emulate since it was one of the first real viral hits on the internet, and they used a lot of clever techniques to cut corners and pull off something incredible based on the limited technology at the time. As for “Interview With Ari,” little did I know that this project would become one of the most challenging and frustrating experiences of my early career, starting when things went completely sideways on the shoot with Jeremy Piven in LA.

I stayed back in New York to work on the incredibly primitive “natural language” parsing engine and the site while the producer went out to oversee shooting the video. They were about 20 minutes into the shoot when I got a frantic call from the producer, who was in tears because Jeremy Piven wouldn’t stick to the script. He kept ad-libbing and refused to return to his marker, which was crucial for me to stitch together seamless transitions between video clips. The engine I built relied on precise scripting to match user input with the correct video clip, so his improvisation threw a huge wrench into the works.

Still from Entourage, Jeremy Piven, HBO.

This project was my first commercial experience shooting in HD, which was cutting-edge technology at the time. We had high hopes for the quality and clarity it would bring to the project. However, when the footage came back, it was a disaster. We chose HD because it was 1920 x 1080 pixels, but the producer didn’t know what she was doing, and they didn’t frame it right. Instead of zooming to fill up the frame with Jeremy Piven at a desk in front of a green screen, it was zoomed all the way out, so he was super tiny. When we started cutting him out, he ended up being about 260 x 300 pixels. Since I didn't have a way of previewing this ahead of time, all the footage we got was unusable.

To make matters worse, the account manager was furious, as if this mess was my fault, even though the producer went out to LA and botched the shoot. I was stuck trying to fix something that seemed beyond salvaging. Emotions were running hot, and I remember being called into her office a few times to get yelled at until I told her I’d just leave if this were how they were going to treat me. I remember talking with the owner, Ian Schafer, who was nice to me and talked me off the ledge. He asked me what I needed to help tackle the mountain of problems, so I brought in my friend Rob Hinds who I had gone to school with at SVA. He had just come off doing the After Effects for 50 Cent’s over-stylized comic book music video, “GATman and Robbin.” 

The technical challenges were immense. We had to work with poorly framed footage, and I needed to edit the video to make it somewhat presentable. Meanwhile, Jeremy Piven's ad-libbing threw off the engine I built to parse user input and match it with the correct video clip. Trying to tie all these elements into a cohesive, seamless experience was a nightmare. Yet, despite all the technical challenges and the chaos of the project, we pressed on. Rob and I spent countless hours trying to salvage the footage, working through the night to make the best out of a bad situation. We cut and spliced to mask the poor framing to make the transitions seamless. 

The other developer on the project was Robin Sneed, who also worked tirelessly on the coding, ensuring the engine could still function despite Jeremy Piven's poor performance. I had created a clever parsing system that would break down the text a person would enter and try to match it up to an XML list of keywords to find the right video clip. We had to compress the video so much to reduce the latency and ensure there wasn’t any buffering, which was common back in the day. Ironically, I worked with Akamai for all the Flash streaming video, and now, 18 years later, I work for them - it’s a small world.

Ultimately, we delivered a “working” site to HBO, but it was far from the seamless experience we had envisioned. The project received mixed reviews, such as this one titled “Entourage' Ari Gold Site Beats A Dead Chicken With A Hammer” by Adrants. The comments are worth a read and sum it up nicely.

The Times was a bit nicer. Using the Internet, HBO's 'Entourage' Finds New Ways to Hook Its Fans, and Ian did an excellent job of trying to publicly defend the work by throwing Piven under a bus:

“Ian Schafer, the founder and chief executive of Deep Focus, said that Mr. Piven, whose character is known for his put-downs and one-liners, ad-libbed much of the taping.”

It didn’t live up to the standards set by the Subservient Chicken campaign. The footage's rough cuts and inconsistencies were evident, and it was a tough pill to swallow. Yet, despite all of that, this project taught me a lot about managing expectations and the importance of clear communication, especially when dealing with high-profile clients and new technology. It also underscored the need for having the right people on the ground during critical phases like filming.

It's not surprising, but I didn’t talk much about this project afterward and was quick to remove it and all my work at Deep Focus from my resume once I had some higher profile jobs like my time working at MLB.com. However, the experience was invaluable. It taught me how to manage a team under pressure and navigate high-stakes projects' complexities. To this day, I still get a bit of PTSD whenever I see a poorly executed jump cut. 

Now that we all shoot on our iPhones and share everything, no matter how poorly edited it may be, the standards have changed to the point where rough cuts are now acceptable. But back then, it was a cardinal sin that could make or break a project. This experience shaped my content creation and production approach, and I always strive for that seamless, high-quality finish despite overwhelming challenges.

About a year after this project, my best friend Howard Attias was filming a party at the Playboy Mansion and called me to let me know Jeremy Piven was there and wanted to know if I had a message for him. I sure did: "Tell him I’m still a fan of the show, and that he ruined my entire project and I’ll never get those two months of my life back!”