Anyone know if it's possible?

I like to watch them in chronological order so I can watch how the interviews evolve and stuff.

It's also interesting to see how covid is brought up and so on.

I would also like to be able to sort videos by length so I can listen to some super long stuff while working.

And in case you're wondering no it does not help at all to work while listening to some of these stories.

Looking for the same answer…

Well, finally took the time to peek under the hood, and without going into the details, here's one solution.

When clicking "all videos" it will direct you to:
softwhiteunderbelly.com/entire-library

So to view the videos in reverse order, you need to append a parameter:
softwhiteunderbelly.com/entire-library?sort=oldest

Looks like the player will also move forward in a chronological order (or, more likely, by date added) but I'm 100% if this works as I hoped.

I will not add a direct link here since clicking random links on the internet is not generally a good idea but I'm hoping most of you get the gist of it.

However, it looks like some content (most likely that which is on youtube anyways) is missing or the ordering is wonky, I'm not sure.

It would not have been much of a deal to view that particular content on Youtube, however YT has recently changed the GUI so that listing all videos and sorting that list is not possible or I haven't figured it out yet.

And on the subject of viewing these in this order, I find it very interesting and inspiring to see how fast he progresses as an interviewer.

Well, took the time to browse "all videos" catalogue towards the beginning and noticed that the ordering is somewhat off.

Sorting by oldest and sorting by oldest AND providing a page to navigate to (?sort=oldest&page=1) seem to return different results and I also noticed that the player is also moving forward in an order I can't quite figure out.

I think the date might be off due to manual ordering of videos as some of them as far as I know were shot long before they were uploaded to this service and so on and so on, so what I consider "original date" is difficult to determine and complicates sorting in the order I then would perceive to be chronological.

As any self respecting scientific study says: More research is needed.