By the time of his fifth album, Havana Daydreamin', Jimmy Buffett seemed to have established a pattern for what a collection of his songs would be. The best one-word description for the musical style still would have to be "country," but Buffett, and probably his record label, had given up on trying to sell him to the conventional country audience, and instead aimed at a slice of the pop market. That was fair enough, since he had evolved a persona as a Gulf Coast ne'er-do-well in compositions full of sentimentally viewed oddball characters ("Woman Goin' Crazy on Caroline Street," co-written with Steve Goodman, a re-recording of "The Captain and the Kid" from his first album, Down to Earth), self-deprecating self-portraits ("My Head Hurts, My Feet Stink and I Don't Love Jesus"), and humorous depictions of life on the road for the working musician ("Big Rig," written by Gregory "Fingers" Taylor, harmonica player in Buffett's Coral Reefer Band, "Kick It in Second Wind," co-written with girlfriend Jane Slagsvol), with plenty of references to alcohol and recreational drugs thrown in. It was perhaps unfortunate that the two best-written songs on the album, each of which ended one side of the LP, were written by others, Jesse Winchester's touching, whimsical "Defying Gravity" and Steve Goodman's road song "This Hotel Room." But that suggested that Buffett was looking for good songs to sing, whether he wrote them himself or not.
AllMusic Review by William Ruhlmann