The two actors starred in Vincente Minnelli's The Sandpiper, which dominated the box office, having made over $13 million against its $5 million budget. Taylor played the leading role of artist Laura Reynolds, while Burton played boarding school headmaster Dr. Edward Hewitt. The drama's storyline focused on Laura's son being sent to boarding school instead of reform school to deal with his legal trouble.
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The track gained more critical acclaim when it was covered by legendary singer Tony Bennettas part of his The Movie Song Album in 1966. It ended up entering the Billboard Hot 100 charts at No. 95 and won a Grammy for Song of the Year. Its popularity led the American Film Institute to tag it as one of the top tracks in American cinema.
Since the 1965 film and 1966 cover, "The Shadow of Your Smile" has been covered by other known artists. Brazilian and American singer Astrud Gilberto covered the track, alongside Wes Montgomery, in 1965. Alongside Bennett, Hampton Hawes, and Oscar Peterson released their versions. Other covers have largely been done by jazz artists like Bill Evans,Benny Carter, and Hank Jones.
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