The iTunes algorithm for shuffling a playlist is total shit. I have a 10 hour โ90s on 9โ playlist, where Iโve heard some songs every single time I shuffle while others have never come up.
— โBadโ Billy Pratt (@KillToParty) February 12, 2020
It likely uses a naรฏve shuffling algorithm which tends to do things like that, instead of a Fisher-Yates algorithm. Too many shuffle functions are bad for just this reason.