During the recording of Big Whiskey and the GrooGrux King, the DMB tragically lost their sax player LeRoi Moore, as a result of injuries sustained in an accident on his farm. This was the only song on the album to feature Moore's replacement the Grammy Award-winning jazz musician Jeff Coffin. Dave Matthews explained to Relix magazine: "Jeff Coffin played an Eastern scale thing, a beautiful solo, one of my favorite things on the record. 'Squirm' was written after Roi had passed on. Otherwise, every saxophone solo moment on the album is LeRoi."
Matthews told Relix about this Eastern-flavored number: "Carter had a drum groove that was pretty awesome but he originally did it over the top of this lilting, melancholy song. And I was like, 'This drum groove is too good for this song! So I took that drum groove and wrote this new song over the top of it. That song is one of the most joyful songs on the record, if not the most joyful, just because I think it's sort of 'be yourself.' It's a song about peace and about acknowledging those things we have in common. For me, I have the image of a convention hall, almost like some strange church, where you go to learn that you're just a naked monkey! And it's not the only simian-themed moment - I went monkey-crazy on this album. I may be the only monkey I know, but I tend to think that I'm not. I watched monkeys all my life and I don't see that the difference is that remarkable. I just have to look at a monkey and know that my granddaddy's, granddaddy's granddaddy was a f--kin' monkey. If you can't see that, damn! I mean, maybe an amoeba's a leap. But a monkey? Good grief!"
Producer Rob Cavallo encouraged Matthews to play some guitar solos on the album, which was unusual for the singer. Matthews describes his solo on "Squirm" as "more just like a wall." He told Acoustic Guitar magazine: "I just sort of went with my heart, which was probably playing ninth chords and trying to find something that sounds nice and then trying to remember it. I just want to make a pretty sound. [Doing solos] was very different for me. But I don't mind - in that situation there's no consequence, in a way, except what you end up with. I guess he was trying to tell me that if you can sing a melody, you can play a melody. Which is true, but I'm incurably lazy."