The Shadow of Your Smile is the eighteenth studio album by American pop singer Andy Williams, released in April 1966 by Columbia Records.

For Williams these selections initiated a trend away from the traditional pop formula that his album output at Columbia up until this point had adhered to.

[10] The Shadow of Your Smile was included in a 2001 box set entitled Classic Album Collection, Vol.

"[13] This album brought the sixth and final Grammy nomination that Williams received over the course of his career, this time in the category for Best Vocal Performance, Male.

The winner was Frank Sinatra for the single "Strangers in the Night", a song that Williams went on to record for his 1967 album Born Free.