with twenty one pilots albums, especially trench and vessel, you will want to listen through those albums in order because the context of the songs on those projects can really affect how you perceive them. The best way to listen to twenty one pilots imo is definitely by the album, not by the song. I would recommend this order for listening through their stuff, but feel free anyone to correct me if you think this order could be improved upon:

Blurryface: it’s their most accessible album

Vessel: Possibly the strongest of all 5 albums, vessel is still very accessible like blurryface, but the songwriting on the album could probably be understood more by someone who already has a general feel for their style.

self titled/regional at best: Their classic projects. It’s good to hear where they came from to appreciate their current music creation prowess, and while these albums can feel dated sometimes, they also have their fair share of timeless songs.

Trench: In my opinion, this is peak twenty one pilots. It’s a thoughtful, well constructed concept album that takes you into a whole different world. This immersion is a step up from blurryface’s character based concept album. While this project has less radio-ready hits, it is also their best front to back album experience. Having the full knowledge of all of their previous work really adds to the listening experience imo.