I'm a huge Herbie fan, and I don't think you can go wrong anywhere from Headhunters and earlier.
Of course, his most well-known titles are stellar, but I'd like to highlight these two (Inventions & Dimensions and Crossings) as two albums that have been incredible surprises to me over the past few years b/c, imho, they're both criminally underrated -- not b/c people don't like them but, rather, they're usually not mentioned in the group of his top-tier titles, and I think they should be.
I can see why this is the case for Crossings bc his Mwandishi trilogy is anything but traditional and, as w/ electric Miles, the jazz establishment was dismissive of anything that didn't swing the way they though "jazz" should swing. Nevertheless, Crossings is probably my favorite Herbie album, and the Speakers Corner press is simply stunning (I also have an OG press that's not in the same league).
As for Inventions & Dimensions, for me, it's been the biggest and best surprise of any of the recent BN series (80/TP/Classics). It's traditional 60s Herbie but with Latin percussion (Willie Bobo & Osvaldo “Chihuahua” Martinez). It's a surprise to me b/c I myself fell victim to the narrower set of titles considered his best and didn't dig into this until the BN80 release. Now it's in the regular rotation.