Dave Chappelle showed up. Thousands of people packed Pioneer Courthouse Square in Portland, Oregon late Tuesday night and into Wednesday morning, drawn by the ethereal promise of an appearance by the popular comedian. They stayed two hours despite a tiny sound system that made Chappelle nearly inaudible, creating one of the most remarkable spontaneous gatherings in Portland history.
The rumor came through Twitter and text and Facebook, and it seemed too good to be true: the wildly popular comic appearing at midnight in the middle of Portland — for free? A mostly 20-something, expectant crowd filled the square until it was crammed full. By midnight thousands stood shoulder to shoulder, forming a bigger crowd than the Greg Oden and playoff rallies the Trail Blazers have held in the square in recent years. Chappelle arrived at 12:53 a.m. to huge applause and people surging toward him, camera phones aloft. When he reached the stage, left in place for the square’s lunchtime summer concert series, he turned on an amplifier the size of a toaster. It was barely audible beyond the first dozen rows of people. One point that did come across: “Portland Police were kind enough not to arrest me,” he said. Chappelle starred in the 1998 marijuana-based comedy “Half Baked,” which he also co-wrote. But he is best known for his wildly popular and often quoted sketch-comedy program, “Chappelle’s Show,” which ran from 2003-2005 on Comedy Central. He stunned fans when he reportedly walked away from a $50 million contract to continue doing the show, and has been somewhat of an enigma since then.
It wasn’t clear why Chappelle was in town, or how the impromptu gathering came about. Though he did say, at one point, “I’m not here for money.” Most people had gone to the square at the last minute, after receiving a text message or other communication from a friend, coworker or roommate. “He played the Bye and Bye (bar/restaurant in Northeast Portland) last night,” 22-year-old Alyse McNeill said. “So I think he’s just doing a tour through Twitter.”
But instead of the 200 people Chappelle said he anticipated showing up at the square, thousands did. He had no entourage and, apparently, not one security guard. Chappelle kept speaking to the crowd, at one point saying he was proud, “when people can stand this close together and not be angry.” Despite the huge crowd police never intruded. Chappelle seemed surprised by the scene. “This has never happened in my entire career,” he said, to a huge cheer. “I’m grateful everybody came out.” Chappelle did squeeze in some comedy. He compared one guy working on the sound system to Scotty from Star Trek, and took an OPB reporter’s microphone and said, “Support Oregon Public Broadcasting.” At one point, a woman and two men atop Starbucks began stripping as Chappelle gaped and the crowd cheered and jeered. By 2 a.m., it was clear the sound system wouldn’t go, and Chappelle wound things down. He thanked the crowd and shared a few things he learned, including: “Don’t tell a secret in Portland.” He left the square at 2:09 a.m. and walked to the Heathman Hotel, where he held court with several dozen fans on the sidewalk. “I’ll catch you on Twitter,” one man said to a friend as he left.