That night I snuck into the Oscars

This happened in 2005. True story.

Oscar Night

Chris Rock will host the Oscars today. The last time he hosted was 11 years ago yesterday, on February 27, 2005. I met him that night. He was cool.

I used to live on N Sycamore Ave, a tiny two-block stretch in the heart of Hollywood. I took the subway to my consulting job downtown every day. The stop was a few blocks to the east, at the corner of Hollywood and Highland, the center of Hollywood’s beating heart.

There you have the Walk of Fame, handprints of movie actors in front of the Chinese Theater, wannabe actors dressed up as super heroes taking pictures with tourists for tips. There’s also Jimmy Kimmel’s studio and the Kodak Theater, the annual home of the Oscars, and somewhere in this mess was my subway. I walked through it all twice each day.

For an entire week my commute was disrupted by the Oscars preparations on Hollywood Boulevard. I had to go the long way around to get to the subway, and the fever pitch of the tourists in the area was increasing all week. The whole thing was really annoying. By Friday, on my walk home from the subway, the red carpet was in place and the area was on total lockdown.

That Sunday night I watched the Oscars alone in my apartment just a few blocks away from red carpet. The best of Hollywood was in my backyard, but they were all out of reach. Towards the end of the show, as the Best Picture award was being handed to Clint Eastwood for Million Dollar Baby, I got an idea.

I put on my best black suit and tie, combed back my hair, and, completely sober, set out toward the Kodak. “They’re just people,” I told myself. “I can be one of them.”

Guard #1: The seat-filler.

I had no plan, but I knew there would be heavy security and I wasn’t sure how close I could get to wherever I was going. I just knew I wanted to find the epicenter, badly.

Scene of the crime. Photo by Loyalty Traveler.

On the backside of the Hollywood & Highland outdoor shopping center where the Kodak calls home, there’s a huge fancy Renaissance hotel. I figured I would start here rather than going straight for the red carpet where every other tourist schmuck was probably also thinking they could sneak in. Security would be thicker on the street side.

You have to think like you belong in order to know where to go. If I came in from out of town and had an Oscar ticket, I’d probably stay at that Renaissance. So that’s where I went.

I met someone standing on the sidewalk a little ways down from where the barricades began. I could tell by all the movement that the Oscars had just ended.

“So, how was the show?” I asked.

“Fine,” was the reply. “I was a seat-filler. Were you?”

I didn’t miss a beat. “Yup.”

“I think the busses back to our parking lot are picking up over there.” She pointed to a bus beyond the first barricade.

“Thanks,” I said, and headed over.

When I approached the guard at the barricade I politely said that I was a seat-filler and heard the busses are picking up there. She pointed me at the bus and let me pass through with no hassle.

First barricade down. Unknown number left to go.

Guard #2: The bus.

Feeling the guard’s eyes on me, I directly approached the bus. Not having any other option, I got on. It wasn’t very full. I took a seat near the front but it didn’t feel right. I didn’t want my night to end at some stupid parking lot down the street. I got up and asked the bus driver how much longer he was going to wait. He said ten minutes, and I said that I’d get a ride with friends instead, exited the bus, and walked down the middle of the street toward Hollywood Boulevard.

This was probably my boldest move of the night. The street was blocked off on both sides. In front of me I could see the headlights of countless limos, and behind me was the bus I was supposed to be on. Within just a few seconds I was approached by a police officer on a bicycle.

“What are you doing?” he asked.

Again I had to think fast. “I left my wallet in the theater. I’m walking back to the carpet.”

“Well, you can’t walk in the street like this. Here, walk through that safety barrier and stay on the sidewalk.”

He escorted me to the sidewalk and sped away. In front of me was the last security checkpoint before the red carpet. Behind me, guarding the entrance to the sidewalk, was probably someone who was supposed to check the badge that I didn’t have. Cha-ching!

Guard #3: The red carpet.

This last guard was both the friendliest and the toughest. I remember she was young and seemed used to hearing bullshit from people trying to more access than they’re supposed to have. My line this time was that I left my badge inside, and was trying to get a ride with some friends who are coming out of the Kodak now.

I tried everything. I changed the subject, talking about the award ceremony as if I’d been inside rather than watching the broadcast. I told her I was a seat-filler and this was my first time at the show. I said a bunch of us were going to the Variety magazine party.

Finally, I pointed at a group of people and said, “Ah, there they are! Can I go through?” I waved at a small group of people I didn’t know. She said no. “Okay, hold on, I’ll call them.” I pulled out my phone and then, finally, she sighed and said those magic words, “Alright, fine, go through.”

I wish I could have given her a high five, but that would have blown my cover.

The Red Carpet

I made it. In just 30 minutes since I left my apartment, I made it much further than I expected, especially given the amount of security and preparations I’d witnessed all week. But I was there, in my cheap dress shoes and black suit I got in high school, standing on the red carpet, surrounded by… nobodies.

I did not meet her on the Red Carpet. Photo by Lester Cohen, WireImage.

I didn’t recognize a single person. That was my first disappointment. I’m on the red carpet, on Oscar night, and there’s not a single celebrity in sight. Just throngs of nicely-dressed people packing into limos and smiling.

I was on the red carpet, but I knew the night should not end there. My first instinct was a good offense. I went right up to someone who looked like a security guard and explained that I’d dropped my badge somewhere and asked if it would be okay if I hunted around for it. He was very nice and said to go on right ahead and try to find it. I said my thanks and headed against the current, toward the Kodak.

It didn’t take me long to find a small group of people who, like me, were moving against the flow. I could tell they had a destination, and I didn’t want to stand out, so I tagged along. Their dress and banter told me they’d been inside and had some special access. I pretended to be ambivalent about them, even displeased that their group was in my way and I’d have to go wherever we were going at their slower pace.

The Governors’ Ball

Together we continued up a series of escalators, winding up on a floor at Hollywood & Highland that I’d never been on before. Prior to the Oscars I used to enjoy sitting out in this shopping center and studying for the LSAT. I knew the structure well, but these guys where going somewhere I’d never been. I just tagged along, ambivalently, still trying not to make eye contact with anyone.

Eventually we came into an entry area, a large outdoor foyer. I saw big security guys talking into ear pieces. Definitely not the same crew that worked the carpet. I walked on, deliberately, hoping that my group would let me blend in. No one ever approached me. I was a stowaway on their boat, and they got me into what I found out later was the Governors’ Ball.

Big night for these two! Photo by

The first celebrity I saw was Clint Eastwood, sitting on a stool next to Diane Sawyer as she interviewed him on camera. He won trophies for Best Director and Best Picture that night. Then I saw all the cameras. They were everywhere! I again found a crowd and tried to look normal. I remember gathering around the Sawyer interview and sensing a very tall man to my right. I looked up. It was Tim Robbins. That’s one big check on my bucket list: I stood next to Andy Dufrane.

Away from the foyer I walked inside where dinner must have been served. I recognized the Wolfgang Puck golden chocolate Oscars from the morning television shows earlier in the week. I wandered around and saw Natalie Portman and Jake Gyllenhaal. I didn’t say hi, but I did lock eyes with them both and then gazed away. I was afraid they might actually talk to me and uncover my little secret.

I caught Clint when he was alone for a moment. I approached and as his body guard stood up I asked him when he’d return to Carmel (where I knew he lives). “As soon as I can,” he said, and looked away. I knew it would be a short conversation.

A group had surrounded Chris Rock, and it looked like he was shaking hands, working the line, so I got right in there. When it was my turn, I said, “I saw your brother do a standup gig on Sunset. He was good.” Chris nodded and said thanks. That was it.

It was a scene like this. Photo by Getty Images.

I didn’t take any pictures (this was before the iPhone) but before I left, I did make one phone call.

“Hey, find someone interviewing Jamie Foxx on TV.”

“What? Where are you?”

“Just do it — I can see them interviewing him.”


“Alright, I’m gonna walk behind him now.” I put my phone down by my side and walked into frame and out of it.

“Did you see me?”

“Dude, get out of there.”

The End

This experience did not change my life. It didn’t make me a better person. It did demonstrate a few concepts that I’ve tried to embrace in other situations.

Look the part, and it’s easy to play it. I don’t wear black suits every day, and I’m not a Hollywood groupie. But I figured I could play one, especially on a day when all the groupies wear the exact same thing. I had a story that made sense, and that combined with the look was all the authorization I needed.

Everyone’s a human. Clint Eastwood was tired. That’s what I remember most about meeting him. In that moment, with just me and his Oscars, he was ready to fall asleep. All those other celebrities I met showed their humanity in other ways. Take away the cameras and on any other day they could pass for attendees of a reception after the local opera. People at the top of their game are still just people, but it’s easy to forget this.

High risk, high reward. I don’t know what would have happened if I’d been caught. Probably nothing too terrible. But post-9/11, everything’s a target, and the local authorities might have taken it seriously. Whatever the risk actually was, it was worth it. I love this story. It’s indicative of me in my 20s. Trying to understand the world better, punching above my weight, figuring out what actually matters.

These were good lessons to learn in my year in Hollywood.

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