Piping images from the Media Library to a sidebar widget

My friend wants to implement a sort of slideshow in the sidebar… in his words –

“Essentially, in our blog posts – we may choose to have media elements. Therefore a blog post might include a video file, an image file, or text or any combination thereof. What we would like is to pipe the image, or video media elements to the upper right hand corner visually – so that the upper right hand corner is constantly rotating between these images. Clicking on the image should take you to the appropriate post from which it is being piped. Therefore, it is another way of exploration.”

Is there any plugin/widget that can accomplish this? Or any other solution / workaround?