Entertainment or educational?
I will start with the DVD's that the Pardeys put out. Very educational. They currently have a box set out, that includes a copy of the interview I did with them on my
radio show. (a little self promotion never hurt anyone

) Horatio Hornblower series is a good entertaining series. One of my favorite movies, if you can find it, is Mystery of the Sands.
Captain Ron is a great no brainer, as I am sure you know by now, but it's fun.
THere are a couple of DVD's about Tristan Jones on EBay right now. I have not seen them, but they sound interesting.
THere was a discovery channel special last year recreating the voyage of the endeavor. I believe it is available on video.
I have more, but don't feel like searching right now, and my memory fails me.