Dave Chappelle performs on stage during the first night of the Oddball Comedy & Curiosity Festival Tour on August 23, 2013 in Austin, Texas. Photo: Gary Miller/FilmMagic

Last night at the Hartford stop of the Oddball Comedy & Curiosity Festival, after being confronted with a group of loud people in the front who were half overenthusiastic and half heckling, Dave Chappelle stopped his set after only a few jokes, sat down on a stool, and did basically nothing until, after 10 minutes, he walked offstage. To get more context about the event, we spoke over e-mail with New York Times comedy critic Jason Zinoman, who recently released the e-book Searching for Dave Chappelle. To write the book, he spent half a year following Chappelle and spoke with scores of his friends and colleagues to try to understand why Chappelle left Comedy Central’s Chappelle’s Show in 2005 in the middle of producing its third season, and the behavior of the press-averse comedian since then. We talked about why he thinks Chappelle did what he did last night, whether it was anti-comedy, and what impact it will have on the comedian’s legacy.

Can you describe Dave Chappelle’s new stand-up style?

He was always more of a storyteller than a quick joke comic, but his yarns have become longer, more ornate and personal in a very specific way. Chappelle’s onstage persona was always the outsider, the sympathetic underdog. The $50 million dollar contract that Comedy Central gave him in 2004 (which could have been as much as $100 million, by the way) that he then walked away from changed that. So his persona changed. He’s using his new reputation as the rare superstar willing to walk away from a fortune and an acclaimed hit TV show at the height of his fame as a really rich subtext in most of his big set piece jokes. To me, that’s incredibly exciting. He’s doing what brilliant comics have long done: Transforming his own dark experiences into hilarious, ambitious art. Of course, that’s only some of the time. Other times, he riffs with the audience, gets booed, and leaves.

Walk me through what you were thinking while watching the clips from last night?

I thought: People are going to go berserk about this. And so they have (meltdown, etc). I was less surprised, because with Chappelle, what’s past is prologue. In 2011 in Miami, he got upset over filming in the audience, stopped telling jokes, checked his phone. That led to boos. The next show went smoothly. The difference is that his new tour has received a lot of attention, so this is much more high profile. But since he became famous, Chappelle has a very striking, occasionally tense relationship with his audience. Recall that his stated reason for leaving Chappelle’s Show was that he didn’t like the sound of a laugh by a white member in his crew. Most comics like all laughs. In this case, Chappelle discriminates between good ones and troubling ones. Of course, he was understandably concerned that white audiences took his racial material the wrong way. But Chappelle has a longer history of wariness toward his crowd. If you look at the first sketch of the third season of his show that they aired in 2006 without his approval, there’s a scene where a fan confronts him and adoration quickly turns to anger. It’s very similar to that famous moment in The King of Comedy where the woman curses Jerry Lewis for not taking time out for her on the street. Chappelle, I believe, distrusts needing the approval of the crowd, even though he wants it too. In his last stand-up special, For What It’s Worth, he tells a Michael Jackson joke that includes a very telling comment rooted in anxiety about fame: “Just remember when you look at that thing he calls his face, he did that for you.”

Why do you think he decided to walk offstage?

Many comics get unhappy with a stand-up show or television executives or whatever. The difference is that Chappelle is willing to leave or stop. He will vanish. He did it on a Fox show in the late nineties. He did it on Comedy Central. An old friend of his from D.C. told me that when Chappelle was young, he used to talk about the career of Bobby Fischer, which I get into in my e-book.

Was any of it intentional? Like when Andy Kaufman read all of The Great Gatsby onstage, was part of this anti-comedy?

I don’t think so.

How are you so sure?

Because he has done similar things before. I mentioned the incident in Miami. In 2004, he did a show in Sacramento where he got very upset with a crowd yelling catchphrases and he walked offstage. And in my reporting, I know from people at Comedy Central that audiences interrupting his stand-up with Rick James quotes was a serious concern of his. He’s a stand-up first. He’s been doing it since he was 14. And he has a history of being sensitive to this stuff onstage and off.

When I first heard he was doing the tour, I was confused. I feel like a festival crowd is the antithesis of Chappelle’s ideal right now. Do you have a sense why he’d agree to do it?

No, I suspect it was not an extremely calculated move. Although I am not surprised he returns in a festival branded as “oddball.” It’s in keeping with how he’s using his reputation in his comedy.

Do you think that part of the problem is that his new style just doesn’t jibe with a festival?

Perhaps. Some have said that this is all about large crowds heckling, which I think only tells part of the story. My issue with the “evil hecklers ruined Dave Chappelle’s set” narrative is that during some shows he really courts and even feeds off of audience interplay. He riffs off comments people yell out and asks questions. I once saw him turn a show into an elaborate question and answer session, like a press conference. Some comics establish a very clear relationship with the audience that is like one at a traditional play. Some shows Chappelle does that, too; other times, like what this one looked to be, he does not or, at least, the lines seem blurred. So I am not excusing the people yelling and booing during the show. They should stop. But context matters. And this is a huge crowd late in the evening. In responding to noise, most comics plow forward, tell their jokes. When Chappelle did not, and instead started chatting with people, the dynamic shifted.

Ultimately, do events like this not only hurt or help him as a touring comedian, but also his legacy as a stand-up?

Both. It hurts him among some fans that paid money to see him or are thinking about doing so. But you could argue that vanishing from the public eye was a spectacular career move, particularly in an era when comics are so accessible. His reputation as an unpredictable renegade makes him more fascinating – and this only burnishes his image. That’s not to say at all that this is part of some master plan, although if it were, that would be amazing.