Dave Chappelle is on the Comeback Trail, but He's Got a Long Way to Go

Dave Chappelle is on the Comeback Trail, but He's Got a Long Way to Go
Photos by Daniel Kramer.

Around five minutes into his Saturday night set, in the midst of a bit about hiring Paula Deen as his personal chef, Dave Chappelle said a line, laughed, shook his body and smiled. If you've ever watched any of his standup specials, it's the move he does when he's surprised and delighted by how funny he is, or just surprised he can get away with saying the things he does.

It was the moment that it sank in that Dave Chappelle was actually on stage doing comedy. It was the moment that made the entire experience real.

It was also one of the few positive moments of the less than hour-long set. While the set was funny, fascinating, even captivating, it would be a stretch to say it was good. Dave Chappelle wants to make a comeback but, if Saturday night is any indication, it's not going to be easy.

When it was announced that Chappelle would be headlining the Oddball Comedy and Curiosity Festival no one knew what to expect. We had gotten so used to talking about Chappelle in past tense that it was hard to imagine what he would be like now. In the end, Saturday night felt more like a classic rock nostalgia tour than a comedy hero returning to the stage to prove that he's still got it.

The issue at hand seems to be one of comfort. By and large, Chappelle looks uncomfortable on stage. There would be pauses where he'd try to think of what to say next. He didn't seem confident in some of the material, and at one point decided not to finish a bit just because he wasn't feeling it anymore.

Although he did have some very funny material on Paula Deen and Oscar Pistorius, material that proves he's not completely divorced from the world at large, he was at his best when he was running through jokes that, while hilarious, were straight out of 2006. His bit about no one in a barber shop talking about Brokeback Mountain is great, but when was the last time you really thought about Brokeback Mountain as a thing that existed? It felt like he was using this older material that he knows is funny as crutch for when he was struggling with where to go next.

Dave Chappelle is on the Comeback Trail, but He's Got a Long Way to Go

He tried, for part of the show, to talk about what happened with Comedy Central and the $50 million contract he walked away from, but it felt like he was doing it more out of an obligation than anything else. Things become blurry when he talks about wishing he still had the money and that integrity is great but you can't "feed on integrity sandwiches." It's the type of talk that will eventually surface in a comedy special and come off as self depreciating and funny but right now comes off as raw and bitter.

The decision to make his comeback via a nationwide amphitheater tour will never go down as the weirdest decision he's ever made, but that doesn't make it any less strange. There's a lot of money to be made by playing for more people, but just because you can get that many people to pay to see you doesn't always mean you should. Add in to the that the solid collection of comedians that opened for him (Hannibal Buress' set featured an incredible cameo by Bun B), and Chappelle has to take the stage every night with a lot of pressure on him.

At least he got paid before the show; he made sure to mention that.

Consider for a moment one of Chappelle's heroes, Richard Pryor. We all know the story of how he ended up setting himself on fire, how everyone thought he was done for, and his triumphant return to comedy in Live on the Sunset Strip. What most people don't know is that the version of Sunset Strip that is beloved by comedy fans wasn't the first show of his return. His first show back Pryor couldn't find a rhythm, and the show was a disaster.

Right now Chappelle still needs to find his rhythm. This show wasn't a disaster, but it's clear there's still work to do. What's also clear is that he still has a great mind for comedy; his new bits might not be particularly groundbreaking, but they are funny and with a little bit of polish could be great. Oddball is only the start of the comeback and, for now at least, the fans are still ready to cheer him on.

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