How Do I Spell Successes? With Six Esses!
In other words: these six (6) song titles all start with ‘S’:

XperDunn plays Piano Covers on July 27th, 2013
Six Song Covers Starting With ‘S’

(“Love is Lovelier”) “The Second Time Around”
“The Shadow Of Your Smile”
“Shangri La”
“Siboney”
“Softly, As I Leave You”
“Stairway To The Stars”
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From Wikipedia, the free encyclopedia:

“The Second Time Around” is a song with words by Sammy Cahn and music by Jimmy Van Heusen. It was introduced in the 1960 film High Time, sung by Bing Crosby with Henry Mancini conducting his orchestra, and was nominated for the Academy Award for Best Original Song.

Its theme is captured by its first two lines:

Love is lovelier the second time around,
Still wonderful with both feet on the ground.

It is especially associated with Frank Sinatra, who released multiple recordings of the ballad.
Jane Morgan sang the song on a 1961 episode of The Jack Benny Program.
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From Wikipedia, the free encyclopedia:

“The Shadow of Your Smile”, also known as “Love Theme from The Sandpiper”, is a popular song. The music was written by Johnny Mandel with the lyrics written by Paul Francis Webster.
The song was introduced in the 1965 film The Sandpiper, with a trumpet solo by Jack Sheldon and later became a minor hit for Tony Bennett (Johnny Mandel arranged and conducted his version as well).
It won the Grammy Award for Song of the Year and the Academy Award for Best Original Song.
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From Wikipedia, the free encyclopedia:

“Shangri-La”
The ‘finale’ song from ‘Shangri-La’, a 1956 musical with a book and lyrics by James Hilton, Jerome Lawrence, and Robert E. Lee and music by Harry Warren. Based on Hilton’s classic 1933 novel “Lost Horizon”
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From Wikipedia, the free encyclopedia:

“Siboney” (Canto Siboney) is a 1929 classic Cuban song by Ernesto Lecuona. The music is in cut time, originally written in C major.
The lyrics were reportedly written by Lecuona while away from Cuba and is about the homesickness he is experiencing (Siboney is also a town in Cuba, and can also refer to Cuba in general)
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From Wikipedia, the free encyclopedia:

“Softly, as I Leave You” is a popular Italian song composed by Giorgio Calabrese and Tony De Vita (1932–1998), translated into English by Hal Shaper.
It was originally an Italian success by Mina, at the Sanremo Music Festival, entitled “Piano” (“Softly”). Mina published a recording of the song first as a single in 1960 and later as well on an EP and on three LPs.

The English songwriter Hal Shaper noticed the song and in November 1961 wrote English lyrics to the melody, calling it “Softly, as I Leave You.” The best known versions are those by Matt Monro (#10 on the British charts in 1962) and Frank Sinatra (#27 on the Billboard Hot 100 and #4 on the adult contemporary chart in 1964).
The Sinatra family announced Frank’s death on May 14, 1998 by placing an announcement on their website that was accompanied by a recording of the singer’s version of the song.
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“Stairway To The Stars” -from the United Artists Motion Picture “SOME LIKE IT HOT”-original song 1935 lyrics by Mitchell Parish, music by Matt Malneck and Frank Signorelli. Glenn Miller’s version has alternate lyrics.