One of the first history podcasts I started listening to was Matt's Today In History. In many ways this was exactly the kind of entertainment I was looking for in podcasts. I remain also very impressed with the quality of the podcast. Matt Dattilo manages to hand on a nearly daily basis a short, informative podcast that is very pleasurable to listen to.
He has got the right voice, the right sound and a well told tale every time. The only reason I stopped listening is because I personally had had enough. At some point I had heard so many of Matt's casts, that I was satiated.
Simultaneously, I had also taken up to listening to history podcasts that are a series, digging into a certain subject, theme or time period, or in other words: were more organized. Matt gives a single history fact, daily, without much connection to the previous or the next. The satiation is then inevitable. But still a recommendable podcast.