For her second Verve LP, Astrud Gilberto expanded her range from a raft of Gilberto/Jobim standards to embrace the large and obviously daunting catalogue of classic American pop. With arrangements by Don Sebesky and Claus Ogerman (as well as two by country-mate João Donato), The Shadow of Your Smile can't help but shine a bright spotlight on Gilberto's weak voice, especially when she's singing material previously enlightened by singers with the weight of Frank Sinatra or Sarah Vaughan. Even the intimate, understated arrangements on songs like "Day by Day," the title track, and "Fly Me to the Moon" overshadow the chanteuse's limited range. Brazilian material like the five songs by Luiz Bonfá make for better listening, though the preponderance of flutes, strings, and muted trumpet in the arrangements is very mid-'60s, for better and worse. (And the notes' description of "O Ganso" as an "exercise in vocalise based on bah and dah sounds" is being more than generous.) Certainly, no American vocalist could hope to equal the tortured syntax and somehow endearing performances on these songs; still, Verve did much better by Gilberto later on when they gave her good-time Brazilian songs to sing and didn't attempt to force comparison with standard jazz/pop vocalists.
AllMusic Review by John Bush