Hopefully the content fits in a few buckets (cartoons, fiction, non-fiction) as far as different terms for rights might go. And then from there, you can lop off anything that's past its copyright term (?). Then maybe the next step is grouping works by the agent/publisher, if any? Or maybe all the contracts with the New Yorker are signed by individuals, with the New Yorker as a publisher. I don't know.
My favorite product that I got to build there was “Cartoons at Random”. You’ll never guess what it did/was!
I miss it terribly, just swiping images off a stack to reveal a new random cartoon underneath.
The developer (Justin?) did an amazing interaction on iOS app (seamless, no jank) and web version was decent too.
They broke it when they migrated from Wordpress to their own Condé Nast CMS
https://www.newyorker.com/cartoons/random/share/1544311
Such delight. Sigh.
The real blocker was permissions and rights. Contracts going back a century obviously never contemplated digital publication, domains, or the internet at all. Untangling who owned what, and securing the right to republish everything online, was a massive legal and logistical undertaking.
That’s what held us back then, not so much the technology. Really glad to see that chapter finally closed.