Memories of the night Dave Chappelle took over Portland – and didn’t even perform

This story first appeared in the October 9, 2013 edition of WW.

Forget the Arab Spring: For me, the true power of social media emerged on July 14, 2009, the day Dave Chappelle shut down Portland. A rumor, spread via Twitter, that the elusive comedian was planning a surprise midnight performance at Pioneer Courthouse Square on a random Tuesday drew one of the largest crowds ever seen in a Portland living room. It seemed like the makings of a wildly successful hoax. It turned out to be just bad event planning.

This week, Chappelle returns to Portland for a legitimate performance at the Schnitz. Even if he ends up infuriating the crowd, as he did in Hartford, Conn., in September, it will hardly compare to the bizarre scene that unfolded that night in 2009. Here’s what I remember from that night, based on my own tweets.

6:55 PM

I come home from how I have been filling my days as an unemployed freelancer and see this on Twitter, from Willamette Week‘s then-assistant music editor Michael Mannheimer: “Is this Chappelle thing real? Or is he just trying to punk the whitest city in America?” Uh, what? Dave Chappelle is in town? A Google search brings me to pdxpipeline.com, which has compiled a series of tweets reporting Chappelle sightings at Masu Sushi, Zach’s Shack, 24 Hour Fitness, the Heathman Hotel, and the now-defunct Hawthorne menswear store Local35, which had announced on its own account earlier that day: “Free Dave Chappelle standup tonight at midnight in Pioneer Square!!” In an attempt to find out what exactly was going on, I tweet Chappelle’s good friend Questlove. He doesn’t respond.

11:00 p.m.

After watching KGW’s live Pioneer Square webcam for a while, I head downstairs to see what’s going on. There are about 100 people hanging around. And there’s a stage set up, although it’s for the Noon Tunes summer concert series, and there’s no PA. Unless Chappelle is planning on skydiving with a sound system strapped to his back, I’m starting to doubt anything is going to happen.

23:41 hours

The crowd slowly swells to over 1,000. It’s getting more crowded up front, and the lack of any real security, combined with the eerily quiet, clearly drunk guy next to me who looks ready to punch the next person he hits, makes me nervous. I try to thin the crowd by starting a new Twitter rumor about Gallagher making a surprise appearance at the Mt. Tabor Theater. It doesn’t catch on.

00:04 hours

Agoraphobia sets in and I leave my spot by the stage. There are now more than 3,000 people in the plaza. “It’s hard to think of a more impressive spontaneous gathering downtown in the history of this city since the Trail Blazers won the NBA title in 1977,” Willamette Week would later report. Officers have blocked off nearby streets. No sign of Chappelle, although a wave is starting.

00:27 hours

Nobody leaves. Two men and a woman crawl into the Pioneer Square Starbucks and strip. There are hippies banging djembes. “It’s like Woodstock,” someone says The OregonianYes, but without real artists, which makes it more like Burning Man.

00:39 hours

I head over to the Heathman, where Chappelle is reportedly staying. A few local celebrity stalkers, including Byron Beck, are hanging out outside. Beck shows me photos he took of Chappelle earlier in the day, confirming that he’s in town. After waiting another 15 minutes, I decide that even if Chappelle is here, he’s staying in his room. I head home.

01:10 am

As soon as I get out of my car at home, I start receiving text messages from WW music editor Casey Jarman, who asks me if the reports that Chappelle has finally appeared are true. I check Twitter and the KGW webcam and, by God, Chappelle is there, with a small portable amp and microphone, looking noticeably more muscular than his Chappelle’s Show days. “Don’t tell secrets in Portland,” he says, though it’s barely audible. “I told four people in the gym, and look what happened.”

Someone leaves to get better equipment. Chappelle passes the time by messing with an OPB reporter, checking out the naked people on the Starbucks roof and continuing to marvel at the turnout. “This has never happened in my entire career,” he says. The man who runs to get a legitimate PA returns but can’t get it hooked up. At 2 a.m., Chappelle admits that there’s no real show going on. “I didn’t know I was still famous,” he says, as the small stage fills up with people taking pictures next to him. “Now I know, and I’m going to be more careful.”

He is driven back to the Heathman, where he stands on the sidewalk chatting with fans on the floor for a few minutes before heading inside. Miraculously, there are no reports of injuries or even arrests.

02:03 am

Jarman texts me that he heard something about Chappelle playing in Thermals drummer Westin Glass’ backyard. “It almost seems too weird to be true,” he writes. Regretting my earlier decision to leave the scene, I drive to Northeast Portland to investigate. It turns out to be a hoax. But crazier things have happened.