how to randomize songs in a playlist

I've been making my own playlists. The problem is how to get the songs to randomly play. Shuffle is not working efficiently. I've got over 800 songs, 8 albums by one artist, 9 or so albums by another artists, with many other artists on the playlist. I don't want to hear the same artist song after song, I want the list mixed up. It would be tedious to do manually. Isn't there a way, a setting to choose to have the list mixed up and randomized? Why is this so complicated, it should be at least 2 clicks and done. Frustrated. Any help is greatly appreciated.