Big Jay Oakerson – The Crowd Work Sessions: I Promised Myself I Wouldn’t Ask

Big Jay Oakerson is back with his follow-up to 2014’s “The Crowd Work Sessions: What’s Your Fucking Deal?!?” This new installment is aptly titled “The Crowd Work Sessions: I Promised Myself I Wouldn’t Ask.”

Anyone familiar with my reviews on this site will know that I have been a huge fan of stand-up comedy for more than three decades. I love and admire the art form, and have a lot of favorite comics.

That having been said, Big Jay Oakerson is, without a doubt, my absolute favorite comic working today. His structured albums, such as 2016’s “Live from Webster Hall” or 2009’s “An American Storyteller” show a comic who is a master storyteller and writer, with impeccable timing. On the flip side, these “crowd work” albums are completely unstructured, and show just how brilliant and talented this comic is even without painstakingly prepared written material.

On each crowd work album, he basically just takes the stage, picks someone out of the audience and begins a dialogue. His ability to turn that into something that will have you on the floor laughing is a testament to his enormous talent. During the first crowd work album, he asked several female members of the audience if they had ever dated a black guy. This new album gets its title from the fact that he “promised himself he wouldn’t ask” that question again on this album, despite the fact that asking people if they ever dated a black guy is his “bread and butter.” I honestly do not think there is another working comic capable of delivering this level of crowd work. I can see someone like Patrice O’Neal doing it, were he still with us, but I do not believe any other living comic could have pulled this off.

As for the actual content, you need to experience this for yourself. Nothing I say in terms of the actual content will do this album justice. Big Jay Oakerson begins by talking to a couple of guys who, based on their appearance, are unlikely friends. He moves on to a couple who just recently separated, but decided to go together to Big Jay’s show. He mines this for everything it is worth, and it’s so much fun to listen to it unravel. Ultimately, he talks to a brother and sister who reveal, just a little too late, that they are related, and this also leads to hilarious treatment. Big Jay’s 15 year old daughter was in the audience during the recording, which he brings up several times. While I am sure there are some prudes out there who think it is “inappropriate” for a child to hear this kind of talk, I cannot even imagine how much fun it must be to have Big Jay riffing at home all the time.

Unfortunately, I live in Los Angeles, so I have never had the opportunity to see Big Jay live. Until I can make that happen, his albums will have to suffice. Go purchase this album. You won’t be disappointed.

The Crowd Work Sessions: I Promised Myself I Wouldn’t Ask
Big Jay Oakerson
Comedy Central Records 2018

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