No, Oliver was not trying to be funny. Oliver was pointing out the truth as he observed it, and at the closing part of his interview offers a solution.

So yes, there was some very harsh criticism during the interview and it was difficult the watch, but it made the interview that much stronger and the solution offered that much more appealing.

It proves that Oliver is not your average 'funny-man' and dares to make part of his show uncomfortable just to establish a solid foundation of his interpretation and proposed solution.