Bowie's last major tour was in 2003 and he played plenty of his old hits. So it doesnt seem like it worked out for him.
>Bowie felt that a burden had been lifted by retiring the old hits he felt he was forced to perform, and said "[Retiring my old hits on tour] was a very selfish thing to do, but it gave me an immense sense of freedom, to feel that I couldn't rely on any of those things. It's like I'm approaching it all from the ground up now, starting with 'Okay, we know what songs we needn't do anymore. What, of my past, did I really like?' You pick things that were really good songs, and you try to recontextualize them, by giving them current, contemporary rhythms. And we've been knocking around ideas like 'Shopping for Girls' from Tin Machine, 'Repetition' and 'Quicksand' from Hunky Dory. Certain songs that I probably haven't ever performed onstage. They're working shoulder to shoulder with the new material, and I'm starting to see continuity in the way that I work."
>Generally, most songs that Bowie performed on the tour were played live in years to come, with only a small number of songs from the Sound+Vision Tour set list truly being retired forever; the most notable songs never to be played live again were "Young Americans" and "Rock 'n' Roll Suicide". Bowie only played "Space Oddity" on tour a single time afterwards, although Bowie did perform the song three times on other occasions. In future tours Bowie would in fact begin to play lesser-known songs, only occasionally punctuated by his well known older "hits", and bias towards playing material written after 1990. After finishing the Sound+Vision tour, Bowie returned to his band Tin Machine for their second album.
It's absolutely worth reading or listening to the whole thing, but one thing that actually took me by surprise was:
BOWIE: Frankly, if I could get away with not having to perform, I'd be very happy. It's not my favorite thing to do. As I say, I don't mind trying it out and making sure something seems to work well. But I really do rather want to move on because I think it's rather a waste of time endlessly singing the same songs every night for a year. And it's just not what I want to do. What I like doing is writing and recording and much more on the - I guess, on that creative level. It's fun interpreting songs and all that, but I wouldn't like it as a living.
Taking it out of context does not do the comment justice, and if you're not as joyless as Lou Reed during an encore (or, for the love of God, during an interview), you should go ahead and listen to or read the whole thing.
https://www.npr.org/2023/08/25/1195632580/david-bowie-the-fr...