I can't think why that would happen. At the most basic I would expect your music to be in a group called "All Tracks" and the automation to pick from that group at random rather than playing in order.
Rather better (but more work and how I did it the second time !) is to create a library structure of folders with each song in the appropriate folder then import each folder into a group of its own. A basic structure might be divided by the decade but you might also want to have pace or style as a consideration.
Once you have your folders build a "clock" for an hour and put the "clock" into the day.
See https://www.playitsoftware.com/Products/Live/Documentation for more info and there are some videos to help.
I am wondering if there is a way to have tracks play in random mode rather that in alphabetical order. all of my track load in order so say every Maroon 5 track would play one after another in stead of mixing tracks up....all of my sweepers play in order so sometimes I will get 2 play in a row or 30 songs will play before a sweeper.
if I have 5 2pac tracks in the list...in auto mode these all play together as the it seems the tracks are grouped in alphabetical order.