8. "I've Always Been Crazy"
Released during the peak of his popularity, "I've Always Been Crazy" was a self-penned hit that doubled as both apology and defiant mission statement. The year was 1978, and Jennings — still reeling from a cocaine bust by the DEA — was tired of being the de facto spokesperson for a movement that grew out of the desire to gain artistic control, not media attention. This take-me-or-leave-me anthem set those frustrations to music. "I've always been crazy... nobody knows if it's something to bless or something to blame," he sang in the song's final verse, letting his own audience judge his fate. They responded by sending the album to the top of the country charts for two months.