Caporaso's early childhood years were an archetype for the kind of musician he would become: born in Italy, moved to Venezuela, and then to Chicago all by the age of three. Vastly different cultures and climates in rapid succession perhaps imprinted him with a taste for variety and a resistance to being classified. Chicago's ability to hold him all the way into his young adult years (when he finally succumbed to the Siren call of Los Angeles) is a testimony to that city's broad musical shoulders.
Night in a Strange Land is difficult to classify. There are many jazz flavors here: free jazz ("My Train," "Last Day," "Night in a Strange Land," "Kurt"); jazz rock ("Generations," "City Wide"); post bop ("Aviary"); blues ("Not Me"); even prairie jazz ("Second Wind"). But even these labels fail whole segments in each tune; Caporaso's songs refuse to follow conventional forms. For example the title track, "Night in a Strange Land," opens with free-form drums and baritone sax, but then hints at a transition into a melody section with some motifs that are doubled on baritone sax and alto sax or baritone sax and guitar; yet the full transition never happens and the piece morphs again into free jazz solos on top of a consistent bed of time kept by the bass and drums punctuated with guitar chords. There a few points where you think it might become a bebop tune but again it never really settles into that defined groove. This "almost one thing, almost another" is the closest thing to a pattern that the tunes actually follow.
Caporaso's electric and acoustic guitar playing is similarly eclectic. He's sometimes comping, sometimes ripping off single-note lines, sometimes strumming, sometimes punctuating with big block chords. On "Generations" he layers in a kind of spacey, open-chorded, phase-shifted sound. On the solo front he gives plenty of room for his bandmates to stretch out; you'll hear some extended bass, sax and drum solos in addition to Caporaso's own improvisations.
A nice added bonus on this album is the recording and mixing, also handled by Caporaso. The instrumental voices are exceptionally clear and well-balanced, demonstrating the talent that has also led Caporaso to winning six Emmys for sound mixing and editing television show soundtracks.