Well-known versions of the song were recorded by Barbra Streisand (on her 1965 album My Name Is Barbra, Two...), singer Shirley Bassey (on her 1966 album I've Got A Song For You), Andy Williams, Al Martino, Perry Como, Nancy Sinatra, Sarah Vaughan and Frank Sinatra. It is also the album title from Astrud Gilberto. Connie Francis recorded the song in English, Spanish (La sombra de tu sonrisa), and in Italian (Castelli di sabbia). Trini Lopez included it on his Reprise Records album (Trini). Lill Lindfors recorded it in Swedish as Din skugga stannar kvar. Marvin Gaye recorded several versions of the song. One can be found on Romantically Yours, another on Vulnerable, and a live version on Marvin Gaye: Live at the Copa. Herb Alpert & the Tijuana Brass recorded an instrumental version for their 1966 album What Now My Love. German singer Udo Lindenberg included a more rock oriented cover of the song on his 1986 single "Germans". In 2006 The Central Band of the Royal British Legion recorded an album with "The Shadow Of Your Smile" as the lead title track.

The Bobby Darin LP Bobby Darin Sings The Shadow of Your Smile was notable in that the album's first side contained all of the songs nominated for the 1965 Academy Award for Best Original Song.

Organist Brother Jack McDuff recorded a purely instrumental cover of the song in his 1967 album "Tobacco Road".

In 1983, instrumental group Pieces of a Dream covered the song from their album "Imagine This."

Tony Bennett re-recorded this song for his album Duets: An American Classic with Colombian-rock singer Juanes in a "Spanglish" version. This marked the first time that Juanes sang in English and Tony Bennett in Spanish.

Vytautas Juozapaitis, a soloist of Lithuanian National Opera and Ballet Theatre recorded a Lithuanian version entitled "Kai Tu Toli" on his debut album Negaliu Nemyleti (Can't Help Falling In Love) released in 2004.

Carly Smithson performed "The Shadow of Your Smile" on Season 7 of American Idol during the top 24 performances. It was released for download from the iTunes store on February 21, 2008.

Singer Amel Larrieux recorded "Shadow of Your Smile" on her 2007 jazz standard album Lovely Standards.

Singer\composer Donald Braswell II recorded this song on his 2007 album New Chapter.

Saxophonist Dave Koz recorded two versions from his Standards album "At The Movies." The first song featured Johnny Mathis on vocals and Chris Botti on trumpet. The second, an instrumental, featured Botti again and guitarist Norman Brown