Discussion: How to make a more dynamic WordPress sidebar?

Back before WP Designer sold out, I read a post he wrote about how static sidebar suck. I couldn’t agree with that idea more. If each page of content on your site is unique (especially blogs) why wouldn’t you want the information in the sidebar to be unique to the content on the page? By creating a more dynamic sidebar you could easily increase user experience, increase page views, and target ads more effectively.

I think WP Designer said it best when he said:

“If every page has unique content or purpose, then why does your sidebar look the same on every page?”

So, my question you is this:

What ideas do you have for making the WordPress sidebar perform better? Id love to here any ideas from practical to near impossible.