Customizable Playlist App

[Ghostlines]

So I was batting this idea around in my head and I wasn't sure how this would work or if it's even possible.

Here's a brief explanation that lead me to come up with this idea. We emulate games and consume old media because it's nostalgic. Not only do we emulate games but we emulate how games looked on a CRT TV, we use bezels, etc to take that extra step for authenticity. I was wondering if that would be possible for mediums outside of games?

For example, my Big Box launches all sorts of media besides just games. So I was looking to tailor fit some features to really immerse the user. Like old game related TV shows. Instead of just having a 22min show without interruptions, I wanted to know if there's a program out there that would make it possible to splice in retro commercials on the fly and emulate how that show would have aired on cable without having to alter the original files.

I tried google to see if there was maybe a more in depth playlist app but I wasn't able to find anything. And it's completely possible, I'm just using the wrong search terms because I'm not sure how to ask for what I want outside of explaining it in depth.

This is what I was looking to achieve:

TV Show - 22min

10 retro commercials - 30sec each as 10 individual files.

Is there a playlist app or program out there that will begin playing the TV Show, then let me insert a break/pause of that file, then cue up any 3 commercial videos (ideally random but ok if it's not), and then after the last commercial, unpause the original video until where the next natural break would occur.  

You guys know of anything? Or think something like this is possible? Launchbox will load simple playlist files for music but I feel like every playlist app is basic and designed for music specifically.