I'm ashamed to admit that despite being a music lover, I am woefully unfamiliar with Bowie. I know a few songs, yes, but I've never sat down and listened to his entire discography, let alone an entire Bowie album. That wrong gets righted starting today as I'm going to start that journey. Any tips for someone in my position?
First up, David Bowie aka Space Oddity
Bowie is captivating for many because he has very distinct periods of output--the box sets do a good job breaking these up.
His earliest stuff easily flows into Space Oddity and the Man Who Sold the World. With his first few albums, I call them the folk hangover period. He was very influenced by the folk wave of the 1960's, but you can tell that he has his own ideas through a lot of these songs. For this period, I would suggest to stick to the studio albums. I have several different recordings of his very early stuff, and while it's fun to see where he came from, it's not integral to getting to know Bowie discography.
Then he hit the Ziggy Stardust era where Bowie starts to create stage personas that help embody the music. Ziggy is arguably the "best" album, if not one of his most popular. It's a strong album, but he still uses conventional instruments. I have a strong feeling that Bowie was heavily influenced by Iggy Pop, as well as glam rock as a whole. He rounded these albums out with Diamond Dogs and Young Americans, which are also extremely strong albums. If you like Space Oddity, you will enjoy this run of albums too. You can see how he evolves sonically--in what I think are baby steps--during this time, but it all has a lot of the same vibe.
After this, Bowie got paired up with Brian Eno and took a definite turn in sound. He's still there, and you see where a lot of his ideas were, but this is a whole new sound. He started adding a lot more synth to his music, and he also got rather extreme during this time. It was known as his thin white duke persona stage, and if the Last Podcast on the Left is to be believed, he ingested nothing but peppers, milk and cocaine for a stint while creating some of these albums. This is when he did Station to Station and my personal favorite album, Low. I really, really love the albums that he did with Eno in the late 70's, and he returns to this sound in the 90's.
He, then, had some billboard success in the 80's with Let's Dance. The next run of albums after this one weren't great because he had signed a contract to deliver 4 albums, and by the second album, he no longer wanted to be in that contract, so Tonight and Never Let Me Down are two that IMHO you can skip, because even Bowie wasn't too jazzed about them.
I have to admit that I haven't listened to much Bowie from the early 90's just because getting my hands on a copy of something like Buddha of Suburbia has proven difficult. I'm looking forward to the newest box, because that's the period in Bowie history that I haven't delved into much. But when I got a CD copy of Earthling back in the late 90's, I think that ultimately got me on the Bowie bandwagon. From the early aughts, the only album I wasn't big on was Reality, but Blackstar made up for that.
tl;dr If you start with the old stuff, I recommend you go in order. I outlined a couple albums that I don't think you should miss and a few you can skip. What I love about Bowie is that he is a master of reinvention. He can change his style completely, but you know it's Bowie because he's so distinct. I think it's best to enjoy his discography in order so that you can follow how each iteration was influenced by the last.