Skip to main content
This story first appeared in the Oct. 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 comic was planning to perform a surprise midnight set at Pioneer Courthouse Square on a random Tuesday drew one of the largest crowds ever to Portland’s living room. It seemed like the makings of a very successful hoax. Turns out, it was just poor event planning.
This week, Chappelle returns to Portland to perform a legitimate gig at the Schnitz. Even if he ends up raging against the audience, as he did in Hartford, Conn., in September, it’ll hardly match the bizarre scene that unfolded that evening in 2009. Here’s what I remember of that night, drawn from my own tweets.
6:55 pm
I get home from however I filled 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 for 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 announced from its own account earlier that day, “Free Dave Chappelle standup at midnight tonight at Pioneer Square!!” In an attempt to find out exactly what is going on, I tweet Chappelle’s good friend Questlove. He does not respond.
11 pm
After monitoring KGW’s live Pioneer Square webcam for a while, I head down to see what’s up. There are about 100 people hanging around. And there is a stage set up, though it’s for the Noon Tunes summer concert series, and there’s no PA. Unless Chappelle plans on parachuting in with a sound system strapped to his back, I start to doubt anything is going to happen.
11:41 pm
Gradually, the crowd swells to over 1,000. It’s getting increasingly packed toward the front, and the lack of actual security—coupled with the eerily quiet, obviously intoxicated dude next to me who looks ready to start swinging on the next person who grazes him—is making me nervous. I try to thin the throng by starting another Twitter rumor about Gallagher performing a surprise gig at Mt. Tabor Theater. It doesn’t catch on.
12:04 am
Agoraphobia setting in, I leave my spot near the stage. There are now more than 3,000 people packed into the Square. “It is difficult to think of a more impressive spontaneous downtown gathering in this city’s history since the Trail Blazers won the NBA title in 1977,” Willamette Week would later report. Cops have blocked off nearby streets. No sign of Chappelle, though there is a wave starting.
12:27 am
No one is leaving. Two men and a woman crawl atop the Pioneer Square Starbucks and strip. There are hippies thumping djembes. “It’s like Woodstock,” someone tells The Oregonian. Yeah, but with no actual performers, which makes it more like Burning Man.
12:39 am
I head to the Heathman, where Chappelle is rumored to be staying. A few local celebrity-stalkers, including Byron Beck, are milling about outside. Beck shows me photos he took of Chappelle from earlier in the day, confirming he’s in town. After waiting about 15 more minutes, I decide that, even if Chappelle is here, he’s staying in his room. I head home.
1:10 am
The second I get out of my car at home, I start getting texts from WW music editor Casey Jarman, asking me if the reports that Chappelle finally showed up are true. I check Twitter and the KGW webcam and, by God, Chappelle is there, with a tiny portable amp and microphone, looking notably beefier than his Chappelle’s Show days. “Don’t tell a secret in Portland,” he says, though it’s barely audible. “I told four people at the gym, and look what happened.”
Someone leaves to get better equipment. Chappelle fills time by screwing around with an OPB reporter, ogling the naked folks on the Starbucks roof, and continuing to express surprise at the turnout. “This has never happened in my entire career,” he says. The guy running to get a legit PA returns, but can’t get it hooked up. By 2 am, Chappelle concedes that no actual show is going to happen. “I didn’t know that I was still famous,” he says, as the tiny stage fills with people taking photos next to him. “Now I know, and I’ll be more careful.”
He’s driven back to the Heathman, where he shoots shit with fans on the sidewalk for a few minutes before retreating inside. Miraculously, there are no reports of injuries or even arrests.
2:03 am
Jarman texts me that he’s heard something about Chappelle doing a gig in Thermals drummer Westin Glass’ backyard. “It almost seems too weird to be untrue,” he writes. Deeply regretting my earlier decision to leave the scene, I roll out to Northeast Portland to investigate. That, it turns out, was a hoax. But crazier things have happened.