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Comedian Dave Chappelle faces the throng at Pioneer Courthouse Square armed only with a tiny amplifier. (Center) Chappelle said he thought a few hundred people might show up. He was mistaken. (Bottom) After the crowd broke up, Chappelle hung out in front of the Heathman Hotel swapping stories with fans.

Photos by Robert Runyon

Last night, more than two thousand Portlanders turned out in Pioneer Courthouse Square to see enigmatic comic Dave Chappelle. Only fifty of us really heard what he had to say.

How do thousands of people materialize at a show that was only mentioned to a few insider types? Behold the awesome power of social media. I’d be tempted to call it a tweet-up, but I realize that’s just about the lamest catch phrase of all time. During Chappelle’s rambles across Portland yesterday, shopping at Local 35, cruising in front of the Keller Auditorium blasting Michael Jackson, eating at Uwajimaya, and buying PA equipment, he would drop hints that he’d be getting up on the stage in Pioneer Courthouse Square that night. (Or as he called it, “Pioneer Place.” It’s kind of absurd to think Chappelle would have his Portland landmarks memorized.)

Then it spread like a laundry detergent commercial: someone told a friend, then a friend told another friend, then a friend tweeted about it on Twitter, then another friend posted it on Facebook, then a radio station picked up the story, and so on, and so on.

By the time I arrived at the square at 11:15, I couldn’t see a brick. Rubberneckers were everywhere, hopping on top of chairs at Starbucks, scaling food carts, climbing MAX stop awnings, and even scrambling to the roof of the Starbucks itself. The impromptu crowd was here to see one man, each person with a different story, from the guy who was dragged there by friends, to the three high school students who heard about it on the radio, to the girl who broke up with her boyfriend that night in order to go.

Understandably, the logistics of dealing with a crowd of 2,000 twentysomethings is daunting, and the Portland Police Bureau acquitted itself well. As per the law, all Portland parks are supposed to close at midnight, and anyone in them should disperse. Obviously, this was a special case. When asked about the situation, a police officer told me, “The law says we should tell everyone to leave. Still, we should weigh the PR pros and cons.” Good call.

They weighed the options. Dave Chappelle won. No one was budging.

As midnight hit, the crowd got restless. Fans tore down the curtains that made up the walls of the stage. Various people got on stage and did Chappelle bits, occasionally inciting cheers from more gullible members of the gathering. Clouds of smoke floated above like mist from a German Expressionist film. By 12:30, the possibility that the night could turn ugly seemed very real. No one wants to deal with that many people, especially when a chunk of them are drunk and looking for a frustration outlet.

Rumors spread that this was an elaborate Andy Kaufman-esque ruse, and that Chappelle was up at the Nines Hotel laughing at the people below. Maybe it was something put on by Twitter to test the effectiveness of social media. Perhaps it was a front for an elaborate heist at the Portland Art Museum to divert the attention of police while Chappelle and Charlie Murphy make off with the collected works of M.C. Escher. OK, that last rumor was mine.

Luckily, at a quarter till one, Chappelle finally showed. The only problem was that his PA system was the size of a George Foreman grill. It was an amp with a mike attached, the kind normally favored by annoying street preachers and obnoxious buskers (or obnoxious street preachers and annoying buskers, if you prefer). It had a recommended range of 1 foot, give or take a foot. Waves of “shut ups” and “shhhs” coursed through the crowd, all in order to hear the words of Chappelle. It didn’t work. Only the first few rows of people heard anything. Chappelle himself was astounded at the turnout. “I didn’t expect this,” he said. “Then again, I haven’t worked in five years. I was only expecting two hundred people.”

For the better part of an hour, he attempted to get more equipment set up to do a real show, but he ran into a snag as Portland Parks cut the power to the square at 1:45. At this point, the crowd seeped onto the stage as it was obvious the show would not go on. Chappelle thanked the crowd. “Tonight was not a complete loss,” he said. “Seeing me is akin to seeing Bigfoot.”

With that, Chappelle left after more than an hour of trying, and the people dispersed too, leaving behind a wake of spent beer bottles and cigarette butts, broken tables, and umbrellas. Somewhere Al Gore burst into tears.

I left with the crowd and headed to my car by on SW Broadway. While walking, I saw a group of people underneath the light of the Heathman Hotel sign. Apparently Chappelle wasn’t done yet.

When I arrived, the group was about fifteen people, and over the course of the next forty-five minutes, it swelled to about forty people. During this time, Chappelle took questions from the audience and spoke with the crowd, bantering with one fellow claiming to be the cousin of martial arts legend Bruce Lee. Surrounded by a sea of cameras and phones, he joked about the final season of his aborted TV show. “How do I know that Comedy Central won’t take all your footage and splice together another episode of Chappelle’s Show?” he said.

When asked about why he didn’t have a bigger PA system, Chappelle invoked the early days of his career, spent telling jokes in the park with a similarly small system. “I wanted to be famous for attention,” Chappelle said of his roots. “Now I’m standing here with Bruce Lee’s cousin.”

At one point, a Haitian father approached, with his young son sitting on his shoulders. Chappelle proceeded to give the child a pep talk, advising him to read up on the history of his heritage, study French, and learn to play an instrument. He then talked at length about the history of Haiti. “This is how I keep the TMZ cameras away,” he deadpanned. “‘Hey Dave, say something funny,’ they ask me. I say, ‘How many soldiers have died in Iraq?’”

He also talked about his whirlwind dose of fame in the early part of the decade. “At one point in my life, shit got so crazy that this shit doesn’t even seem crazy,” Chappelle told a growing crowd in front of the Heathman at 2:30 in the morning.

Chappelle had an easy, friendly manner about him, and built a rapport with everyone he met, trading jokes, even laughing at their lesser witticisms.

I asked Chappelle why he came to Portland, but he didn’t respond. In retrospect that’s probably a good thing. Do we really need to know the reason why Chappelle, one of comedy’s biggest names, would try to do a free show in Portland after five years of playing J.D. Salinger in Ohio and Africa? We should just thank our lucky stars that he did. —Robert Runyon