The album was produced and arranged by Ben Folds and most of the songs are co-written by Folds and Shatner, with Folds creating arrangements for Shatner's prose-poems, and features guest appearances from Joe Jackson (on a cover of Pulp's "Common People"), Folds and Aimee Mann (backup vocals on "That's Me Trying"), Lemon Jelly (on "Together"), Henry Rollins, and Adrian Belew (on "I Can't Get Behind That"), and Brad Paisley (on "Real", which he wrote specifically for Shatner).
Joe Jackson explained his involvement in an interview, saying, "That came through Ben Folds, who's a big fan of mine. You’d have to ask him how he got hooked up with Bill Shatner, I don't remember. But I think he did a really great job of putting an album behind Shatner that is fun and not completely cheesy, though when it is too cheesy, it's deliberately so. (laughs) It's just a very musically satisfying record, and when he asked me to be a part of it, why would I not? How could I refuse? I went to Nashville for a few days and hung out with the two of them, and we created a couple of masterpieces." He ultimately said about working with Shatner, "He's wonderful, very musical, and very funny, because he's so obviously in on the joke".