I recommend Hunky Dory: It was his first truly great LP, and probably has more in common with the track The Man Who Sold the World than does the LP of the same name. Bear in mind that Ziggy was recorded very soon after Hunky Dory but is pitched much more as a rock ‘n’ roll LP, and you’ll get some sense of just how much the man was developing as an artist during this period. From there, I’d fast forward to ‘76 and Station to Station to see what global domination, satanic persecution fantasies, fascistic leanings and cocaine did to him (in a word, stunning), then see how he pulled things back working with Eno on Low, Heroes, and Lodger, before stopping to admire the confidant work of a genuine legend on Scary Monsters. You can definitely take a breather then before embarking on any of a half dozen other journeys through Bowie’s oeuvre. Later highlights include Heathen and Outside, but your mileage may vary.