My Finest Work Yet finds Andrew Bird grappling with themes of current day dichotomies and how to identify a moral compass amidst such divisive times. "I'm interested in the idea that our enemies are what make us whole – there's an intimacy one shares with their opponent when locked in such a struggle. If we were to just walk away would our enemies miss us? How did we get to this point and how can we, through awareness of it, maybe pull ourselves out of this death spiral," says Bird.

He tackles these topics with a more direct songwriting approach than his previous releases, taking greater risks both lyrically and in recording. Bird and the band taped all the songs live without headphones or separation attempting to create a sound where all instruments bled into each other's microphones. Of the new music, Bird reflects, "There is a certain optimism to this record...it's pretty up musically though it doesn't pull any punches when it comes to the lyrics." Produced by Paul Butler, My Finest Work Yet was recorded at Barefoot Recordings in Los Angeles, CA.

New single, "Sisyphus," is titled after the Greek king punished by Zeus for trying to outsmart the gods and cheat death. Bird shares that the track, "is about being addicted to your own suffering and the moral consequences of letting the rock roll." Previous single, "Bloodless," which debuted in November 2018, also appears on the new album. Written after the 2016 election, Bird states, "‘Bloodless' has always been the template for the rest of the album. It took me a while to step back and say, ‘What can I say that's going to be helpful?' I feel like if I'm going to contribute to anything, it should be coming from some perspective that we haven't yet thought about."