All of Me Gerald Marks and Seymour B. Simons (Published in 1931). Originally in the film Careless Lady, starring Joan Bennett. Sinatra recorded it three times — in 1946, for his film Meet Danny Wilson, starring Shelley Winters (1951), and for Swing Easy (1955). The song was originally a #1 hit by Louis Armstrong in 1932.
All the Way Sammy Cahn and Jimmy Van Heusen (1957). An Academy Award-winning song from The Joker Is Wild, starring Sinatra and Mitzi Gaynor. Sinatra recorded the song twice, for All The Way (1960) and for Sinatra’s Sinatra (1963).
The Best is Yet to Come Cy Coleman and Carolyn Leigh (1961). First appeared on It Might As Well Be Swing (1964). Previously a hit for Mabel Mercer, Peggy Lee, Sarah Vaughn, and Tony Bennett.
Blue Skies Irving Berlin (1926) recorded in 1941 under Tommy Dorsey and his orchestra. Released on the album The Voice.
Can I Steal a Little Love? Phil J. Tuminello (1956). Recorded by Sinatra in 1956, and appeared on Forever Frank. The song was also heard in Rock, Pretty Baby, starring Sal Mineo.
Change Partners Irving Berlin (1938) a popular song written for the 1938 film Carefree. Featured on Frank Sinatra's 1967 album, Francis Albert Sinatra & Antonio Carlos Jobim.
Cheek To Cheek Irving Berlin (1934) a popular song written for the Fred Astaire film Top Hat. Featured on Frank Sinatra's 1958 album, Come Dance With Me.
Chicago, Chicago Fred Fisher (1922). Recorded by Sinatra in 1957, and heard in The Joker Is Wild. The song first appeared on Come Fly With Me. Previously a vaudeville song sung by Blossom Seeley.
Dindi Aloysio De Oliveira, Ray Gilbert and Antonio Carlos Jobim (1966). First appeared on Francis Albert Sinatra & Antonio Carlos Jobim, a collaboration between Sinatra and the foremost Brazilian interpreter of bossa nova music.
Dream John H. Mercer (1944). Originally heard in Her Highness and the Bellboy, starring Hedy Lamarr and was the closing theme song to composer Johnny Mercer’s radio show. Sinatra recorded it in 1945 (with the Ken Lane Singers), and again in 1960, which appears on Nice N’ Easy.
Drinkin’ Again John H. Mercer and Doris Tauber (1962). Recorded as a single in 1967. Appears on the album, The World We Knew.
Fly Me to the Moon Bart Howard (1954). First recorded by Sinatra (with Count Basie) for his It Might as Well Be Swing album.
Guess I’ll Hang My Tears Out to Dry Sammy Cahn and Jule Styne (1944). From the failed Broadway musical, Glad To See You (closed in Boston). Sinatra recorded the song twice, in 1946 for The Essential Frank Sinatra, Volume 2 and in 1958 for Frank Sinatra Sings For Only The Lonely.
Here’s to the Losers Jack Segal and Robert Wells (1963). First recorded by Sinatra for his Softly As I Leave You album.
High Hopes Sammy Cahn and Jimmy Van Heusen (1959). From the Frank Capra film, A Hole in The Head, starring Sinatra, Edward G. Robinson and Eleanor Parker. It won the Academy Award for Best Song and was used by John F. Kennedy in his campaign for President. It first appeared on Sinatra’s All The Way album.
How About You? (I Like New York In June) Ralph Freed and Burton Lane (1941). Written for Judy Garland for the film, Babes On Broadway. Sinatra recorded the song twice — with The Tommy Dorsey Orchestra (1941), and for his album, Songs For Swingin’ Lovers (1956).
I Believe Sammy Cahn and Jule Styne (1946). From the film It Happened in Brooklyn, starring Sinatra, Jimmy Durante, and Kathryn Grayson. Sinatra recorded the song in 1946 for the film, and in 1957 for This Is Sinatra, Volume 2.
I Get a Kick Out of You Cole Porter (1934). Originally sung by Ethel Merman in the musical Anything Goes. Sinatra first recorded the song for Songs For Young Lovers (1953), and again for Sinatra And Swingin’ Brass (1962).
I Love Paris Cole Porter (1953). From the Broadway musical Can-Can. Sinatra starred in the 1960 film version of Can-Can along with Shirley MacLaine and Maurice Chevalier. Sinatra and Chevalier first recorded this song as a duet for the soundtrack. Sinatra recorded it a second time for Frank Sinatra Sings Of Love And Things.
I Only Have Eyes for You Al Dubin and Harry Warren (1934). Written for the Busby Berkley film Dames, which starred Dick Powell and Ruby Keeler. Sinatra recorded the song on a 1945 V-Disc, the only recordings made during WW II. It was shipped for military use only. He recorded it again with Count Basie in 1962 for Sinatra And Basie. The discs were first released for commercial sale in 1994. The first hit recording was made by Ben Selvin And His Orchestra in 1934.
I’ll Be Seeing You Sammy Fain and Irving Kahal (1938). The song was introduced in Broadway’s Right This Way. Sinatra originally recorded the song with The Tommy Dorsey Orchestra (1940), but it didn’t become a hit until it was rereleased in 1944. He recorded the song again in 1961 for his album, I Remember Tommy.
Indian Summer Al Dubin and Victor Herbert (1919) as a piano piece by Herbert, Al Dubin added lyrics to the song in 1939. Recorded by Sinatra in 1967 for Francis A., Edward K (Duke Ellington). The song was a big #1 hit for Tommy Dorsey before he hired Sinatra.
It Was a Very Good Year Ervin M. Drake (1961). Recorded by Frank Sinatra in 1965 for the September Of My Years album, the song can also be heard frequently on HBO’s “The Sopranos.”
It’s All Right With Me Cole Porter (1953). From the Broadway musical, Can-Can. Sinatra starred in the 1960 film version of Can-Can — the year he was named Top Box Office Star by the Film Exhibitors of America. Sinatra recorded the song for the soundtrack, and again in 1984 for the L.A. Is My Lady album.
I’ve Got the World on a String Harold Arlen and Ted Koehler (1932). Recorded by Sinatra in 1953 as a single. It first appeared on the 1957 album, This Is Sinatra. Originally recorded in 1933 by Cab Calloway.
I’ve Got You Under My Skin Cole Porter (1936). From the film musical Born To Dance, starring Eleanor Powell and Jimmy Stewart. It was recorded by Sinatra in 1956 for the album, Songs For Swingin’ Lovers and in 1963 for his album, Sinatra’s Sinatra. One of Sinatra’s most requested tunes.
L.A. is My Lady Alan Bergman, Marilyn Berg-man, Quincy D. Jones and Peggy Lipton (1984). The title song from Sinatra’s 1984 album.
The Lady is a Tramp Richard Rodgers and Lorenz Hart (1937). From Broadway’s hit Babes In Arms. The song was added to the 1957 film version of Rodgers and Hart’s Pal Joey, starring Sinatra, Rita Hayworth and Kim Novak.
Let’s Face the Music and Dance Irving Berlin (1936). First heard in the Fred Astaire, Ginger Rogers film, Follow The Fleet. Sinatra recorded the song twice — in 1960 for the album, Ring-A-Ding-Ding, and in 1979 for the Trilogy series (Record One — The Past).
Let’s Get Away From It All Thomas Montgomery Adair and Matt Dennis (1940). Sinatra recorded this song twice — with Tommy Dorsey (along with the Pied Pipers and Connie Haines) and in 1957 for the album, Come Fly With Me.
Makin’ Whoopee Walter Donaldson and Gus Kahn (1928). Written for Eddie Cantor for Ziegfeld’s Broadway production of Whoopie. Recorded by Sinatra in 1956 for the album, Songs For Swingin’ Lovers.
Moonlight Serenade Glenn Miller and Mitchell Parish (1939). Recorded by Sinatra in 1965 for Moonlight Sinatra. The song was band-leader Glenn Miller’s theme song.
My Funny Valentine Richard Rodgers and Lorenz Hart (1937). From the Broadway hit, Babes In Arms. Recorded by Sinatra for the 1953 album, Songs For Young Lovers.
My Kind of Town Sammy Cahn and Jimmy Van Heusen (1964). Written for Sinatra for the 1964 film, Robin and the Seven Hoods, which starred Rat Packer’s Dean Martin, Sammy Davis, Jr., and Bing Crosby. Originally heard on the My Kind Of Town soundtrack.
My Way Paul Anka, Gilles Thibault, Claude Francois, and Jacques Revaux (1967). Originally written in French as “Comme d’Habitude” (“As Usual”). The song first appeared on the 1969 Sinatra album, My Way. One of Sinatra’s most popular and most requested songs.
(Theme From) New York, New York John Kander and Fred Ebb (1977). Written for the film of the same title, which starred Robert De-Niro and Liza Minnelli. Sinatra recorded it in 1979 for the second album in his Trilogy series, (Record Two — The Present). One of Sinatra’s most performed songs.
Nice N’ Easy Alan Bergman, Marilyn Berg-man and Lew Spence (1960). Recorded by Sinatra for the 1960 album, Nice N’ Easy.
One For My Baby (And One More For The Road) Harold Arlen and John H. Mercer (1943). Originally sung by Fred Astaire in the film, The Sky’s The Limit, Sinatra recorded it in 1947, and again in 1958 on Frank Sinatra Sings For Only The Lonely. The first singer to have a hit record with this song was Lena Horne in 1945.
The Same Old Song and Dance Sammy Cahn, Jimmy Van Heusen, and Bobby Worth (1958). Recorded in 1958 for the album Come Dance With Me.
Should I Reveal? Nacio Herb Brown & Arthur Freed (1930). Originally written for Lord Ron of Broadway, starring Charles Kaley. Sinatra recorded the song in 1950 for the Love Is A Kick album, &1960 for Sinatra’s Swingin’ Session.
Something Stupid C. Carson Parks (1967). The song was a duet with Sinatra and his daughter Nancy and first appeared on his 1967 album, Frank Sinatra.
Something Wonderful Happens in Summer Joseph Bushkin and John De Vries (1956). Sinatra recorded the song in 1957, and it appears on the 1958 album, This Is Sinatra, Volume 2.
South of the Border (Down Mexico Way) Michael Carr and James B. Kennedy (1939). Originally a huge #1 hit by Shep Fields & His Rippling Rhythm Orchestra. Sinatra recorded it in 1953; it appeared on 1957’s This Is Sinatra.
Summer Wind Hans Bradtke, Heinz Meier (Henry Mayer), John H. Mercer (1965). Originally written in German; Mercer translated Bradtke’s lyrics. Sinatra recorded it in 1966 for the album Strangers In The Night.
That Old Black Magic Harold Arlen and John H. Mercer (1943). Originally written for Star Spangled Rhythm, starring Betty Hutton, it was a huge #1 hit for Glenn Miller & His Orchestra. Sinatra recorded it in 1946 for The Voice, and in 1961 for Come Swing With Me.
(Love Is) The Tender Trap Sammy Cahn and Jimmy Van Heusen (1955). Written for the film, The Tender Trap, starring Sinatra and Debbie Reynolds. Sinatra recorded it in 1955 for This Is Sinatra and in 1962 for Sinatra And Basie.
This Is All I Ask Gordon Jenkins (1965). Sinatra recorded the song in 1965 for the album September of My Years.
Wave Antonio Carlos Jobim (1968). Sinatra re-corded this song in 1969 for Sinatra And Company (1970).
Where or When Richard Rodgers and Lorenz Hart (1937). From Broadway’s Babes In Arms. Originally a big #1 hit for Hal Kemp & His Orchestra in 1937. Sinatra recorded it in 1945, for the album The Voice, and in 1958, for Frank Sinatra Sings Songs For Only The Lonely.
Witchcraft Cy Coleman & Carolyn Leigh (1957). Sinatra recorded the song as a single (appeared on the 1960 compilation All The Way) and for Sinatra’s Sinatra (1963).
You Go to My Head J. Fred Coots and Haven Gillespie (1938). Sinatra recorded the song twice — in 1945 and in 1960. The first appeared on Frank Sinatra Story In Music and the second appeared on Nice N’ Easy.
You Make Me Feel So Young Mack Gordon and Josef Myrow (1946). From the film, Three Little Girls In Blue, starring June Haver and Celeste Holm. Sinatra recorded the song in 1956 for the album, Songs For Swingin’ Lovers.
Young at Heart Carolyn Leigh and Johnny Richards (1953). Sinatra recorded the song as a single, and it first appeared on the 1957 album, This Is Sinatra. The song inspired a movie of the same title, which starred Sinatra and Doris Day.
You’re Cheatin’ Yourself (If You’re Cheatin’ On Me) Al Hoffman& Dick Manning. Sinatra recorded this song in 1957 - it appeared on This Is Sinatra, Volume 2.