The AJAX Futures package (for ASP.NET) introduces a new tag: <asp:Media runat="server" /> which uses Silverlight to play media. The client tag is rendered as an EMBED tag in Firefox and an OBJECT tag in MSIE (don't know that I like that, but it works).
The control is skinnable (including some built-in skins), it's able to be databound, so you can place the control in a repeater and pass the media's URL and effectively load a bunch of media files from a datasource (whether that's an object, XML file, database, array, whatever).
As a "native" ASP.NET control, the IDE has full access to the properties, intellisense, etc.
What's cool, you can add chapter-style navigation to allow jumps within the media, not only that but you can have time-based events to fire off code to, say, write a "closed caption" experience (displaying plain text in a div, timed to the video), or play advertisements in a div that are triggered from a point on the timeline of the media clip, etc.