Dave Chappelle has been playing surprise shows in the Bay Area for a while now and I had the fortune of seeing one recently thanks to a comedienne friend of mine giving me a heads up.

The reason I say “I had the fortune” is because I haven’t really decided if it’s good fortune or misfortune. I feel extremely fortunate that I got the tickets, despite them being $67 a pop it was worth it to see the famous Dave Chappelle live on stage. At the same time I have really mixed feelings about the show!

Dave Chappelle is known for his insane comedy endurance and previously setting a comedy endurance record by performing for over six hours. The excitement was palpable, both my girlfriend and I were excited to see the man that made us laugh on TV many a night. The show was at the Punch Line in San Francisco, we didn’t have any problem parking on a week night which was a pleasant surprised and the club was absolutely packed. I felt extremely lucky to have gotten the tickets that I did.

The show opened with a performance by W. Kamau Bell, a very funny comedian who actually played at Skyline earlier in the semester! It was more than a pleasant surprise to see him and some of his fresh material. Osama bin Laden was of course a topic amongst both Chappelle and Bell and they both had funny material about it.

The first hour and a half of Chappelle was great, it had me laughing and I definitely feel like I got my money’s worth. However it was after that hour and a half that things got weird, depressing even. The comedy show seemed to turn more into a bizarre question and answer session with more than half of the audience afraid to speak. I suppose most people would be afraid to speak to one of the funniest men in America for fear of being humiliated.

The show started at 10:30 in the evening with Bell opening for about maybe 30 minutes. Chappelle went on until at least 2:30 in the morning. I say at least 2:30 in the morning because both my girlfriend and I had class in the morning and had to leave early. While the question and answer session was incredibly weird and awkward at times there were moments in it that just had me dying of laughter from Chappelle’s quick wit.

Chappelle even admitted that the show was incredibly weird, and said he felt like the crowd was looking for something but he didn’t know what it was. There were also less kind words he said about his own show which made things feel even more awkward.

I used the word depressing before because Chappelle mentioned some things that quite frankly had me a little worried. He said things along the lines of “you have no idea how different comedy is going to be with me gone,” “I feel like the world is ending at least for me soon” and one other joke that sounded like depression. I’m probably reading too much into it though. On the off chance that I’m not, I hope Chappelle doesn’t do anything crazy, as he has a lot of fans around the world who love him.

I feel like the show was well worth the money despite the weirdness, I just feel like Chappelle is struggling to overcome the vast celebrity power he has. A lot of people just want to know about his disappearance but he just wants to do comedy and I think he just keeps getting distracted by people who throw questions at him. This question and answer format is really hit and miss though and more often than not it’s miss.

If you’re interested in seeing Chappelle do a stand up show I’d say follow all the local comedy clubs you can on Facebook. They’re bound to mention it before tickets go on sale, giving you a nice leg up over the competition.