Recorded in 1958 for the album Chet Baker Sings: It Could Happen To You, this rendition of "Do It The Hard Way" showcases Baker's dual artistry as both vocalist and bandleader. The tune, composed by Richard Rodgers with lyrics by Lorenz Hart, originally appeared in the 1940 musical Pal Joey and carries a witty, self-aware lyric about the merits of taking the difficult path. Baker delivers the vocal with his characteristic lightness and rhythmic ease, swinging at a brisk tempo of around 169 BPM in the key of E-flat. His phrasing is relaxed yet propulsive, demonstrating the effortless cool that defined the West Coast jazz aesthetic. Following Baker's vocal chorus, pianist Kenny Drew takes a full chorus solo that is harmonically inventive and rhythmically buoyant, complementing Baker's understated approach with a more assertive pianistic voice. The 32-bar AAAB form provides a sturdy framework for both soloists to explore. This session, recorded during Baker's European period with a Danish rhythm section, captures a moment when the trumpeter was refining his vocal identity, moving further from the bebop idiom of his early career toward a more intimate, singer-focused aesthetic. The interplay between Baker and Drew throughout the track exemplifies the relaxed yet attentive ensemble dynamic that characterizes the entire album.
