“Requiem for a Shuffle: Why Steve Jobs Told Me He Loved the Littlest IPod—And Why We’re Going to Miss It”, 2017-08-02 (; backlinks; similar):
…Price aside, the iPod Shuffle kept alive the practice of having the computer sequence one’s music, a phenomenon that I found continually fascinating…My biggest obsession was the shuffle function. My favorite thing to do with my iPod was to shuffle my entire music collection, and marvel at what songs came next. Sometimes the segues would be so perfect that it seemed a genius deejay was behind the wheel. I compared such acts of algorithmic serendipity to the “Hand of God” chess move that Deep Blue used to confuse Garry Kasparov into thinking the computer had trespassed into realms formerly limited to brilliant humans.
…Early in my iPod experience, I found reason to question the mechanics of shuffling, as I noticed that when I shuffled my fairly large music collection, the iPod played a suspiciously large number of Steely Dan songs. At one point, I brought up this issue with Steve Jobs and pressed him to reveal whether the shuffle was truly random. He was vociferous in insisting that it was. He even got an engineer on the phone—he wouldn’t share the guy’s name with me—who vowed that yes, the shuffle was random. I wrote about this in Newsweek and got a huge reaction from people with similar experiences. [But they were all wrong.]
So it was particularly satisfying to me that on the day Jobs introduced the iPod Nano in September 2005, he also launched a feature that one could use on all iPods to adjust the shuffle. It was called “Smart Shuffle”, and allowed users to dictate whether they preferred mixes where songs by artists might be clustered, or not.
“Smart Shuffle came from people complaining that songs aren’t random”, Jobs said, not needing to specify that I was the biggest complainer. “And of course it really is random, and we go talk to them and they say, ‘There’s two Bob Dylan songs right after another, how could it be random?’ and you explain to them it could happen, [and in fact] it often does. What they really want is to make sure that it doesn’t happen. Rather than argue whether it’s random or not, we can give them the outcome they want.”
Good times.