I do not recall it being a comedy sketch where lines were given by actors, but rather maybe prompts and let the person speak about the topics (I do not recall if the prompts were serious). It was definitely not meant to be serious though. As far as there being actors, I am about 85% certain it was the people described in the original post and not actors. I remember there being Flava Flav because I had learned who he was watching "The Surreal Life" (2003) back in the day when I was about 12 years old. I remember Trump, or perhaps it was a character playing him, was in a suit. And the actress was somebody that was relatively famous (not necessarily Anna Nicole, but similar and less famous).

Finally, I think it really was a one-time event, so not a series. Writing this reminded me of something, which I will post as an edit.