Of the Bowie post-Tin machine stuff I would agree that 1. Outside is probably the best, however, I also think that its predecessor Black Tie White Noise is a a real forgotten gem. A totally different kind of album - produced by Nile Rodgers therefore more accessible, but unmistakably Bowie. Definitely more personal, with references to his marriage to Iman and the suicide of his brother. By going back to working with Rodgers and Eno at that time it's like Bowie was carefully reaching into his past for inspiration while at the same time driving forward with new ideas.
Also from that era - The Buddha of Suburbia soundtrack album is very good, and somewhat akin to 1.Outside
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