I did a full listen through of their non-kids albums not long ago. I think it's fair to say that they get a bit more "mainstream" with each album. I think the first, eponymous, album is the purest distillation of their sound.
Don't get me wrong, I love everything through the 90s, and I think John Henry, Long Tall Weekend, and Mink Car get slept on for how many great tracks there are. There are plenty of great songs after Mink Car, but things start to feel a bit sterilized.
But that first album has so many great, creative songs all over the genre map. Everything Right is Wrong Again, Number Three, Nothing's Gonna Change My Clothes, I Hope That I Get Old Before I Die, Alternation's for the Rich, Rhythm Section Want Ad, all bangers.
I almost feel like there's a bit of a curve. I think some time post-Disney (maybe The Else to Join Us) was when they started getting back more to themselves, though not to the same extent as Pink Album. I think I Like Fun is especially good for the current era, and Book has some bangers too - Brontosaurus almost feels like peak 90s Johns.
Part of it is I think the Johns tend to mirror a genre at the time - Pink album was New Wave, Lincoln was on the border between alt and alt rock, Flood was the John's own quirky alt rock, John Henry was more mainstream alt rock, Factory Showroom was when the Johns figured out how to better take alt rock and fit it to their vibe, Long Tall Weekend channeled just a bit of swing revival, Mink Car was early 2000s pop/rock, and most recent albums are a mix of modern indie and alt rock.
I agree with you on Pink album, though - it has such great vibes, and it's tied in my heart with Lincoln.
I also listened to the albums in order recently and noticed the same. The first album is the most creative and eclectic in many ways, and each album loses a little of that essence but the production values get noticeably better.
That said, my favourite is probably Lincoln which is nearly as crazy as the first, but with slightly better songwriting IMO.
I also love John Henry in a different way; the songwriting and production is as good as TMBG gets, but it definitely has a different vibe to the first two albums.
I find most post-90s TMBG albums get very much slept-on. I also love The Else and Glean, but again they have an entirely different vibe to the first couple of albums.
I had a friend back in the 90s who had a theory that your favorite TMBG album is the one you were listening to when you get it. When it goes from being weird but catchy, to true fandom.
Unpopular opinion incoming.. I was listening to the albums in order recently. I love the first three from start to end, but I couldn't get through Apollo 18 without having the urge to skip Mammal and Dinner Bell - I find the vocal melodies really grating in those tracks.
Having Fingertips shuffled around the album almost makes up for it, if you're listening to a proper version which doesn't have them bundled into one track.
Apollo 18 does have some great tracks, but I think my favorite oscillates between the pink album, Lincoln, and whatever album I'm listening to that I neglected before (currently, The ELSE - you could say I'm Impressed.)
Apollo 18 was my favorite for a long time, especially listening on shuffle to give Fingertips the intended playback method. But a few years ago I really got into Factory Showroom thanks to my partner. That album is has a lot of really solid songs that showcase the range of their songwriting skills.
Also, streaming services forcing Fingertips to be a single track has made listening to Apollo 18 way less fun.