Released on Verve in 1965, The Shadow of Your Smile captures Astrud Gilberto in the early ascent of her solo career, placing her understated, conversational vocal style at the center of lush yet subtle arrangements by Don Sebesky and Klaus Ogerman that emphasize clarity, warmth, and emotional transparency across bossa nova, jazz, and mid-60s pop material. Produced by Creed Taylor, the album frames her soft, unforced delivery with gentle orchestral color, whether on the newly minted standard of the title track, Brazilian selections, or contemporary ballads, allowing the nuances of her timbre and phrasing to carry the music. As a whole, it marks a key moment in Gilbertos evolution from guest vocalist to fully realized solo artist and affirms her as a defining voice of the bossa nova era.

Tracklist:
Side A
1. The Shadow of Your Smile
2. (Take Me to) Aruanda
3. Manh de Carnaval
4. Fly Me to the Moon
5. The Gentle Rain
6. Non-Stop to Brazil

Side B
1. O Ganso
2. Who Can I Turn To?
3. Day by Day
4. Tristeza
5. Funny World