Portland loves Dave Chappelle. Tickets to his surprise Portland appearance at the Aladdin Theater sold out in four seconds flat last week. That should shock no one who remembers the teeming masses that showed in 2009 for his impromptu non-show at Pioneer Courthouse Square. Or his sold-out run at the Helium in 2014. 

There's nothing Portlanders like more than a good, long line to stand in. Lucky for the 600 ticketed fans, last night, Chappelle's line snaked—nay, pythoned—around the block for several hours before the 7pm show. After the pat-down and mandatory phone surrendering, the beer and pizza line inside seemed equally daunting. I couldn't check my phone's clock, but it sure felt like a long time before the show began. 

But when Chappelle finally appeared, all of that was instantly forgotten.

He was honest, offensive, and deeply, deeply hilarious, just like you knew he would be. He talked about Donald Trump's bluster and Ted Cruz's "hall monitor swag." He talked about running into OJ Simpson at different points of his career. He talked about Caitlin Jenner and Bill Cosby. He talked about Nike dropping boxer Manny Pacquiao from a sponsorship deal. He even joked about collecting evidence for Making a Murderer's Steven Avery in Manitowoc County.

But what elevates Chappelle's routine above mere pop culture observations is his self-consciousness. He's uneasy with fame, but also loves its perks—like when he joked about gleefully accepting Chris Rock's invitation to this year's Oscars, boycott be damned, or about learning of Jenner's transition long before the media from Kanye. He can sell out crowds, but insecurity still haunts him. In one especially memorable bit, he recalled the gnawing jealousy he felt when he took his starstruck son to a Kevin Hart show—a friend of his who happens to be much more popular these days. It sounds sadder here than it was when he delivered it. 

And despite the ironclad security, Chappelle exuded warmth. He bought wine for people in the front row—one woman, a cancer survivor he had met at a previous show in Eugene, another, a hippie in a tie-dye shirt he made fun of for, well, the obvious reasons. He also revealed that he had secured tickets for the woman who was turned away from the Tuesday show after paying a scalper $750 for tickets. 

In one of the most personally revealing moments of the night, he advised a 17-year-old in the front row not to go to college unless he truly had passion for learning. That provoked some half-hearted boos from the back where I was sitting, but Chappelle soldiered on, repeating the advice his father had given him as a teenager:

"Would you rather be loved or be right? You can't be both."