Frank Sinatra / Jack Wolf / Joel Herron / 4:51
Frank Sinatra first recorded “I’m a Fool to Want You” in 1951 with Ray Charles’s vocalists. The song was released as the B-side of the single “Mama Will Bark,” reaching number 14 on the Billboard Pop chart. Since Sinatra’s second version, released in 1957 by Capitol Records on the album Where Are You?, numerous performers have covered this romantic song, including Chet Baker, Billie Holiday, Art Farmer, and Elvis Costello. Bob Dylan delivers a well-crafted version with an excellent vocal performance, admirably backed by his outstanding musicians.
Matt Dennis / Tom Adair / 3:24
There are many great versions of this song, including Frank Sinatra’s on the album Where Are You? and Chet Baker’s on Embraceable You, both recorded in 1957, and, more recently, Diana Krall’s version on her album The Look of Love, released in 2001. Almost half a century after Sinatra, Dylan sings this jazzy interpretation with the voice of a crooner. His performance is delicate and filled with emotion. The simplicity of the orchestration, especially the brass arrangements by D. I. Harper, contributes wonderfully to Dylan’s vocal work.
Jerome Moross / Carolyn Leigh / 2:56
“Stay with Me” is a song that can be heard in the 1963 American drama The Cardinal, directed by Otto Preminger. Dylan’s recording stays close to the original. “Stay with Me” is the only title on Shadows in the Night, besides “That Lucky Old Sun,” that Dylan has performed onstage to date. He sang it at the conclusion of a concert at the Beacon Theatre in New York City on December 3, 2014.
Joseph Kosma / Jacques Prévert / Johnny Mercer / 3:02
“Autumn Leaves,” originally a French song, “Les Feuilles Mortes (Dead Leaves)” was written by French poet Jacques Prévert with music by Hungarian-French composer Joseph Kosma. In 1949, Johnny Mercer wrote English lyrics, and “Autumn Leaves” became a pop and jazz standard. The song has been covered by many artists, including Frank Sinatra, Chet Baker, Nat King Cole, John Coltrane, Eric Clapton, and Iggy Pop. Dylan’s version features a part on pedal steel guitar by Donnie Herron and shows a new sweet and elegant side of the songwriter.
Cy Coleman / Joseph McCarthy / 3:38
This is a wonderfully sentimental song that in 1952 concluded Frank Sinatra’s work with Columbia Records. Bob Dylan recorded an emotional version of it. Somewhat surprisingly, his vocal presents a freshness he seemed to have lost years ago. Guitarist Donnie Herron provides an excellent pedal steel guitar part.
Oscar Hammerstein II / Richard Rodgers / 3:28
“Some Enchanted Evening,” from the 1949 musical South Pacific, is the most popular song from a Rodgers and Hammerstein show. Again, this beautiful melody has inspired many performers, the latest being Dylan himself. Perry Como’s version in 1949 reached number 1 on the charts. There is an outtake of this song dating from the sessions for Under the Red Sky (March 1990).
Buddy Kaye / Ted Mossman / Sergei Rachmaninov / 3:26
“Full Moon and Empty Arms” is a song by Buddy Kaye and Ted Mossman, based on Rachmaninov’s Piano Concerto, no. 2. Frank Sinatra recorded the song in 1945, followed by Erroll Garner (1946), Eddie Fisher (1955), Sarah Vaughan (1963), and Bob Dylan. Dylan’s highly refined version contrasts with Sinatra’s more sober and haunting interpretation.
Harold Adamson / Jimmy McHugh / 3:37
Harold Adamson had a long career as a composer in Hollywood. The song “Where Are You?” appears on the soundtrack of Top of the Town (1937), a musical directed by Ralph Murphy and Sam White. It was first performed by Gertrude Niesen and covered by many artists, including Frank Sinatra in 1957. Dylan delivers a convincing interpretation.
Irving Berlin / 3:21
“What I’ll Do” is one of the most famous love songs written by Irving Berlin for his Music Box Revue. Sung in 1923 by Grace Moore and John Steel, this romantic song was also made popular by William Atherton when it was featured in The Great Gatsby (1974), starring Robert Redford and Mia Farrow. “What I’ll Do” is a popular standard, recorded by many artists from Paul Whiteman to Chet Baker, Art Garfunkel, Harry Nilsson, Nat King Cole, and Frank Sinatra. Dylan himself delivers a powerful homage to the brilliant Irving Berlin with the emotional expression and deep feeling of the voice and instruments.
Haven Gillespie / Beasley Smith / 3:39
Composed in 1949, “That Lucky Old Sun” was a tremendous success for Frankie Laine, spending twenty-two weeks on the charts and peaking at number 1. Subsequently, other adaptations brought success to Frank Sinatra and the Jerry Garcia Band. Dylan remains faithful to Sinatra’s version, with a beautiful vocal performance. He performed this song in Sydney on February 24, 1986, with Tom Petty and the Heartbreakers, and from time to time thereafter.