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It seems most people are complaining about when Spotify plays random stuff it thinks you like, but I'm having the same issue with my actual created playlist. I've carefully gathered and downloaded all my favorite songs into a playlist that has about 3 days worth of music on it... Yet it plays the same 100-200 or so songs no matter what, even on shuffle. I'm pretty sure most songs in this list have never been played. Very irritating
That's because Spotify shuffle by default is not a simple true randomizer as most would expect. It tries to be "smart" and mixes your playlist so similar songs play after another, while avoiding playing songs from the same artists back to back. And some more variables. In theory this is great and works well for some users and focused playlists, but can ruin playlists that cover a very wide range of genres and styles.
You can better approach true randomness by disabling the "Automix" feature in Spotify settings. Not entirely sure if you then actually get true randomness (Spotify loves being opaque), but I hope it helps with your playlist at least.
I would love if they made some enthusiast options available so we could customize our own Automix and shuffle preferences, but that will never happen...
i just preshuffle my playlist using a playlist shuffler website and then go in the order its shuffled. just got to remember what song you left off on, that way every song gets played at least once