Apart from two gentle ballads, "Girl I Can Tell" and "Whistlers And Jugglers," which are both plaintive above-average standard country fare, the rest of ["I've Always Been Crazy"] finds Jennings living up to his image as a wandering, wild-living anti-Establishment hell-raiser, cocking two fingers at society. "I've Always Been Crazy" has the delicious second line, "but it's kept me from going insane". This and "Don't You Think This Outlaw Bit's Done Got Out Of Hand" … find him treating the whole outlaw image with tongue firmly in cheek.
By contrast, "Billy" is a sensitive dialogue with an old good-time buddy about getting too old for the outlaw life and settling down. Can't help feeling that there's an autobiographical slant to this and the two aforementioned songs. Is Waylon going soft? Will he be recording with strings again? The mind boggles. Possibly the answer lies in "As The 'Billy World Turns," the weirdest cut of the pack. It starts out simply enough, about writing a song, but then things, well, get a little fuzzy around the edges…. [Proceedings] gradually degenerate into something approaching a boozed-up impromptu session amid empty bottles of Jack Daniels in a border town bar room. Fascinating. Don't be put off by the cover, which finds The Man looking like an extra from Moby Dick, nor by the [Buddy] Holly medley; investigate for the rest of the content.
Robin Grayden, "Albums: 'I've Always Been Crazy'," in Melody Maker (© IPC Business Press Ltd.), January 13, 1979, p. 23.