It was only playing the same song twice if people have the same song twice in their library or playlist. The only other possibility with either shuffle software is if you have it on shuffle repeat all, and it just so happens that the last song in the first shuffling is also the first song in the next. This can still happen today, but it is increasingly rare the larger your playlist is.

The issue back then was how it would randomly play the same artist twice in a row, or manage to play songs from an alum sequentially. Truly random shuffling.

Steve Jobs coined the term “less random” because the then-new shuffle would intentionally avoid playing the same artist or songs from the same album twice in a row.