Noob question on playlists

I have a project. I want to make a cartoon box for the kids. I have a big pile of old cartoons in individual files that I wish to play in a random order.

I’ve attempted to figure this out by myself, but while I am tech savvy, I’m not educated in linux, and a lot of the “help” articles I’ve found assume basic knowledge I apparently don’t have.

From what I’ve been able to determine, a smart playlist can be set to shuffle play (what I’m after), but I think it needs files to be “in the libraries” which is accomplished with a scraper. Honestly I don’t give two hoots whether I have pictures or proper metadata. I just want OSMC/Kodi to look at a particular folder, recurse through the sub folders, and play everything in random order.

While I’m not well versed in linux, I’m not afraid of a command line and I’m good at following instructions or using instructions to point myself toward the resources I need. I just don’t “speak” linux, and the last time I did any coding to speak of it was in Turbo Pascal on 5.25" floppies (still have it in a box in the closet).

Please help. Anything would be useful at this point.

RPi 3(whatever was current a year or so ago, not the new +)
Various media sources (Mostly Dlink 321 NAS’, and a WD Mycloud I’m doing this project on)
OSMC on auto update so it’s likely current, at least through July or so.

This is not important. It’s Kodi that you want to specify the behavior of. The Kodi wiki is quite a good resource for understanding and interacting with Kodi itself. You should start there.

Yes, Kodi is designed for the purposes of providing these libraries and serving the media from them. You will likely find more info on exactly what you are trying to achieve by searching in the Kodi forums. You are certainly not the only person that has sought such a behavior.

There is a random video addon I use which should give you what you want. It works through your library as well as the files. Or it least it should depending how your files are organised I suppose.
Install it via the Kodi Repo > Context Menus > Play Random Videos.
There are a few settings you can configure and then to start play just highlight the source / directory, bring up the context menu and select Play Random.
Works well for me I can choose a random movie, or a random movie within a certain genre or play random episodes of specific TV shows.

The Kodi wiki is long on information, but pretty short on actual directions for those of us that haven’t ever worked with it on a granular level. Its failure at answering my question with it is what drove me here.

As an example, the not-smart playlists entry says they are plain text files, but mentions zero on how that file is formatted. I’d prefer not to just dump everything into a single folder, and how the plain text playlist file is formatted is important if I need to recurse down a couple levels to get to the actual files (typically show\season).

I’ve been using OSMC for a couple years now, but I’m doing it in a non-sophisticated way. I have Network storage of various types, I just created a Videos, Files entry that pointed to all the various appropriate folders on the NAS’ That is fine for playing a single file, or a series of files, but not so good for Shuffle. Currently I have it set up to go to the next file automatically so I could just point at the top folder and hit Play, but then everything is always in the same order. Not enough variety to keep kids entertained.

How do I get stuff IN to the libraries?
Do the files have to be named in a particular fashion?
Or is it flexible enough to work with my clearly labeled files as is?
The wiki mentioned .nfo files, is there a good tool that I can point at a master folder and it will crawl through and create nfo files as it goes?
Is there some tool that can generate the “dumb” playlists if I point it at my folder(s)?
Can “dumb” playlists use shuffle mode?

Here’s where my self taughtedness kicks me in the butt.

After a bit of noodling I managed to find and install that add on, but now where do I find it?
Does it need lists already? Or can I just point it at folders?
Restart the Pi to see it?

If it matters, I’m using the OSMC skin.

In order to see and configure it go to addons > my addons > all
No need for pre populated lists.
I use it with all my media scraped to the library an it works very well for me.
I tested it briefly on on just unscraped files and it seemed to function the same but this all could depend on exactly how all your folders are nested within each other.
My files have all be arranged as per the Kodi recommendations.

You are a prince among men. Even if I can’t get this to do what I want, I appreciate your efforts.

It works for me. I mostly use it to watch random Simpsons episodes.

After a bit of noodling I think I have it working for me.

If you have a boatload of videos will it take several minutes to start?

It’s working. Just randomly hopped from one cartoon to another in a vastly different folder (indeed, different physical device). Were it possible, I’d send you a package of Oreos through the internet.

Now to go set it up on the kids Pi…

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