Apodado «la Voz», fue una de las principales figuras de la música popular del siglo XX y dejó, a través de sus discos y actuaciones en directo, un legado canónico en lo que respecta a la interpretación vocal masculina de esa música. Su popularidad llegó a ser inmensa y prácticamente constante a lo largo de toda su vida, aunque fueron especialmente exitosos los años cuarenta y cincuenta, siendo esta última década, con su producción discográfica para la compañía Capitol, la considerada como su etapa de mayor calidad como cantante.

Su repertorio se basó en la obra de los más importantes compositores populares estadounidenses, como Jimmy Van Heusen, Cole Porter, Sammy Cahn o George Gershwin, y su estilo sintetizó, ya en sus orígenes, quince años de influencias mutuas entre la música de inspiración jazzística y la música pop que empezaba a difundirse a través de la radio. Sinatra construyó su estilo sobre la base de una comprensión natural de la música popular, tal como la habían entendido Bing Crosby, Fred Astaire, Benny Goodman y Louis Armstrong, explotando la idea de que esta, en todas sus vertientes, debería ser una extensión de la conversación.

Técnicamente, se caracterizó por su cuidada precisión en el fraseo y su dominio del control de la respiración; el rango de su voz estaba próximo al de bajo-barítono. En cuanto a su categoría artística, esta radica en su capacidad interpretativa para transmitir las emociones y sentimientos implícitos en las letras de las canciones.

A Sinatra se le reconoce el haber sido el primer cantante que hace un uso consciente de los medios de amplificación del sonido con el objeto de situar su voz por encima del sonido de la orquesta (dominadora de la música popular estadounidense de principios del siglo XX) y para aproximarla a la intimidad del oído del oyente.

Como actor, Sinatra fue un artista de tipo intuitivo, reacio a someterse a los ensayos y repeticiones habituales en una grabación, por lo que sus interpretaciones fueron emocionalmente intensas al tiempo que irregulares. La importancia en su vida de su trabajo de actor fue capital; por ejemplo fue precisamente a través de su papel en De aquí a la eternidad como logró salir de un bache personal y artístico en el tránsito de los años cuarenta a los cincuenta para encumbrarse en lo más alto de la popularidad, además de ganar por su interpretación el Óscar al mejor actor secundario.

A lo largo de su carrera profesional, Sinatra grabó más de 1300 canciones y participó en más de cincuenta películas. Recibió multitud de premios y homenajes, entre los que se cuentan diez premios Grammy, otorgados por la Academia de Artes y Ciencias de la Grabación, y la Medalla de la Libertad del gobierno estadounidense.

Sencillos
Big band singer I: Harry James Orch. (Columbia)
1939 From the Bottom of My Heart (Brunswick label)
1939 It’s Funny to Everyone but Me
1939 Here Comes the Night
1939 My Buddy
1939 On a Little Street in Singapore
1939 Ciribiribin
1940 Every Day of My Life
1940 All or Nothing at All (re-issued 1943)

Big band singer II: Tommy Dorsey Orch. (RCA Victor)
1940, 11 Feb, The Sky Fell Down
1940, 11 Feb, Too Romantic
1940, 26 Feb, I’ll Be Seeing You
1940, 26 Feb, Moments in the Moonlight
1940, 26 Feb, Shake Down the Stars
1940, 04 Mar, Polka Dots and Moonbeams
1940, 04 Mar, Say It
1940, 12 Mar, The Fable of the Rose
1940, 12 Mar, This is the Beginning of the End
1940, 25 Mar, Imagination
1940, 25 Mar, Yours Is My Heart Alone
1940, 29 Mar, Devil May Care
1940, 29 Mar, Fools Rush In
1940, 29 Mar, Hear my song, Violetta
1940, 23 Abr, East of the Sun
1940, 23 Abr, Head on my Pillow
1940, 23 Abr, It’s a Lovely Day Tomorrow
1940, 23 May, All This and Heaven Too
1940, 23 May, I’ll Never Smile Again
1940, Jun 13, Whispering
1940, Jun 27, The One I Love Belongs to Somebody Else
1940, Jun 27, Trade Winds
1940, Jul 17, Call of the Canyon
1940, Jul 17, I Could Make You Care
1940, Jul 17, Love Lies
1940, Jul 17, The World is in my Arms
1940, Ago 29, Our Love Affair
1940, Ago 29, Tell me at Midnight
1940, Ago 29, Looking for Yesterday
1940, Ago 29, We Three
1940, Sep 09, April Played the Fiddle
1940, Sep 09, When You Awake
1940, Sep 09, Anything
1940, Sep 09, April played the Fiddle
1940, Sep 17, I’d Know You Anywhere
1940, Sep 17, You’re Breaking My Heart All Over Again
1940, Oct 16, Do You Know Why
1940, Nov 11, Stardust
1941, Jan 06, Oh! look at me Now
1941, Jan 06, You Might Have Belonged to Another
1941, Jan 15, You lucky people, You
1941, Jan 15, It’s Always You
1941, Ene 20, I Tried
1941, Ene 20, Dolores
1941, Ene 20, Without a Song
1941, Feb 07, Do I Worry
1941, Feb 07, Everything Happens to Me
1941, Feb 17, Let’s Get Away from It All
1941, May 28, I’ll never let a day pass y
1941, May 28, Love Me as I Am
1941, May 28,Free for All
1941, May 28, This Love of Mine
1941, Jun 27, I Guess I’ll Have to Dream the Rest
1941, Jun 27, You And I
1941, Jun 27, Neiani
1941, Jul 15, Blue Skies
1941, Ago 19, Two in Love
1941, Ago 19, Violets for Your Furs
1941, Ago 19, The Sunshine of your Smile
1941, Ago 19, Pale Moon
1941, Sep 18, I Think of You
1941, Sep 18, How do you do without Me
1941, Sep 18, A Sinner Kissed an Angel
1941, Dic 22, How about You
1942, Ene 19, The Night we called it a Day
1942, Ene 19, The Lamplighter’s serenade
1942, Ene 19, The Song is You
1942, Ene 19, Night and day
1942, Feb 19, Snootie Little Cutie
1942, Feb 19, Poor You
1942, Feb 19, I’ll Take Tallulah
1942, Feb 19, The Last Call for Love
1942, Mar 09, Somewhere a Voice Is Calling
1942, May 18, Just as Though You Were Here
1942, May 18, Street of Dreams
1942, Jun 09, Take Me
1942, Jun 09, Be Careful, It’s My Heart
1942, Jun 17, In the Blue of Evening
1942, Jun 17, Dig Down Deep
1942, Jul 01, There Are Such Things
1942, Jul 01, Daybreak
1942, Jul 01, It Started all over Again
1942, Jul 02, Light a Candle in the Chapel

Los primeros singles (RCA Bluebird)
1942 The Night We Called It a Day
1942 Night and Day
1942 The Lamplighter’s Serenade
1942 The Song Is You

Los años Columbia
1943 You’ll Never Know
1943 Close to You
1943 Sunday, Monday & Always
1943 If You Please
1943 People Will Say We’re in Love
1943 Oh What a Beautiful Morning
1944 I Couldn’t Sleep a Wink Last Night
1944 A Lovely Way to Spend an Evening
1944 White Christmas
1944 Saturday Night Is the Loneliest Night of the Week
1944 I Dream of You
1945 What Makes the Sunset
1945 Ol’Man River
1945 I Should Care
1945 Dream
1945 Put Your Dreams Away
1945 Homesick That’s All
1945 If I Loved You
1945 The Charm of You
1945 My Shawl
1945 Lilly Belle
1945 Nancy
1945 America the Beautiful
1945 The House I Live In
1946 Oh! What It Seemed to Be
1946 Day by Day
1946 Full Moon and Empty Arms
1946 All through the Day
1946 They Say It’s Wonderful
1946 From This Day Forward
1946 Soliloquy (Label Columbia Masterworks)
1946 Five Minutes More
1946 One Love
1946 Begin the Beguine
1946 The Coffee Song
1946 Silent Night
1946 Jingle Bells
1946 September Song
194? This Is the Night
1947 That’s How Much I Love You
1947 I Want to Thank Your Folks
1947 It’s the Same Old Dream
1947 Sweet Lorraine
1947 I Believe
1947 Mam’selle
1947 Almost Like Being in Love
1947 Tea for Two
1947 Ain’tcha Ever Comin’ Back
1947 Christmas Dreaming
1947 I’ve Got a Home in That Rock
1947 So Far
1947 It All Came True
1947 You’re My Girl
1948 What’ll I Do
1948 But Beautiful
1948 For Every Man There’s a Woman
1948 But None Like You
1948 I’ve Got a Crush on You
1948 All of Me
1948 It Only Happens When I Dance with You
1948 Nature Boy
1948 Just for Now
1949 Kiss Me Again
1949 My Melancholy Baby
1949 Autumn in New York
1949 Senorita
1949 A Little Learnin’ Is a Dangerous Thing
1949 Sunflower
1949 Why Can’t You Behave
1949 Comme Ci Comme Ca
1949 If You Stub Your Toe on the Moon
1949 Bop! Goes My Heart
1949 Some Enchanted Evening
1949 The Right Girl for Me
1949 The Hucklebuck
1949 Let’s Take an Old-Fashioned Walk
1949 It All Depends on You
1949 Don’t Cry Joe
1949 Bye Bye Baby
1949 If I Ever Love Again
1949 That Lucky Old Sun
1949 Mad About You
1949 The Old Master Painter
1950 Sorry
1950 Sure Thing
1950 Chattanoogie Shoe Shine Boy
1950 Kisses and Tears
1950 American Beauty Rose
1950 Poinciana
1950 Peachtree Street
1950 Goodnight Irene
1950 Life Is So Peculiar
1950 One Finger Melody
1950 Nevertheless
1950 Let It Snow, Let It Snow, Let It Snow
1951 I am Loved
1951 Take My Love
1951 Love Means Love
1951 You’re The One
1951 We Kiss in a Shadow
1951 Love Me
1951 I’m a Fool to Want You
1951 It’s a Long Way from Your House to My House
1951 Castle Rock
1951 April in Paris
1952 I Hear a Rhapsody
1952 Feet of Clay
1952 My Girl
1952 Luna Rossa
1952 Bim Bam Baby
1952 The Birth of the Blues

Los años Capitol
1953 I’m Walking Behind You b/w Lean Baby
1953 I’ve Got the World on a String b/w My One And Only Love
1953 From Here to Eternity b/w Anytime, Anywhere
1953 South of the Border b/w I Love You
1954 Young at Heart b/w Take A Chance
1954 Don’t Worry ‘Bout Me b/w I Could Have Told You
1954 Three Coins In The Fountain b/w Rain (Falling From The Skies)
1954 The Gal that Got Away b/w Half As Lovely (Twice As True)
1954 It Worries Me b/w When I Stop Loving You
1954 The Christmas Waltz b/w White Christmas
1954 You, My Love b/w Someone To Watch Over Me
1955 Melody of Love b/w I’m Gonna Live ‘Till I Die
1955 Why Should I Cry Over You? b/w Don’t Change Your Mind About Me (con June Hutton & The Pied Pipers)
1955 Two Hearts Two Kisses
1955 Learnin’ the Blues
1955 Not as a Stranger
1955 Same Old Saturday Night
1955 Love and Marriage
1955 The Tender Trap
1956 Flowers Mean Forgiveness/You’ll Get Yours
1956 How Little We Know/Five Hundred Guys
1956 You’re Sensational/Johnny Concho Theme
1956 Well, Did You Evah?
1956 Mind if I Make Love to You
1956 Hey, Jealous Lover
1956 Can I Steal a Little Love/Your Love for Me
1959 Come fly with me
1957 Crazy Love/So Long, My Love
1957 Your Cheatin’ Yourself
1957 All the Way/Chicago
1957 Witchcraft
1957 Mistetoe and Holly
1958 Nothing In Common/How Are Ya Fixed for Love
1958 Monique
1958 Mr Success
1958 To Love and Be Loved
1959 French Foreign Legion
1959 High Hopes
1959 Talk to Me
1960 River, Stay away from My Door
1960 Nice ‘n’ Easy
1960 Old MacDonald
1961 My Blue Heaven
1961 American Beauty Rose
1962 I’ve Heard That Song Before
1962 I’ll Remember April
1962 Hidden Persuasion

Los años Reprise de Frank Sinatra
1961 The Second Time Around / Tina
1961 Granada / The Curse of an Aching Heart
1961 I’ll Be Seeing You / The One I Love (Belongs to Somebody Else)
1961 Imagination / It’s Always You
1961 I’m Getting Sentimental Over You / East of the Sun (and West of the Moon)
1961 There Are Such Things / Polka Dots and Moonbeams
1961 Without a Song / It Started All Over Again
1961 Take Me / Daybreak
1961 Pocketful of Miracles / Name It and It’s Yours
1961 The Coffee Song
1961 Ring a Ding Ding! / Nothing but the Best (A Souvenir Of Cal-Neva Lodge)
1962 Stardust / Come Rain or Come Shine
1962 Ev’rybody’s Twistin’ / Nothin’ but the Best
1962 Goody Goody / Love Is Just Around the Corner
1962 The Look of Love / I Left My Heart in San Francisco
1962 The Look of Love / Indiscreet
1962 Me and My Shadow (con Sammy Davis, Jr.) / Sam’s Song (por Sammy Davis, Jr. y Dean Martin)
1963 Call Me Irresponsible / Tina
1963 I Have Dreamed / Come Blow Your Horn
1963 A New Kind of Love / Love Isn’t Just for the Young
1963 Fugue for Tinhorns / The Oldest Established (con Dean Martin y Bing Crosby)
1963 Have Yourself a Merry Little Christmas / How Shall I Send Thee? (por Les Baxter’s Balladeers)
1964 Stay with Me (Theme from ‘The Cardinal’) / Talk to Me Baby
1964 My Kind of Town / I Like to Lead When I Dance
1964 Softly, as I Leave You / Then Suddenly Love
1964 Hello Dolly (con Count Basie)
1964 I Heard the Bells on Christmas Day / The Little Drummer Boy (con Fred Waring & His Pennsylvanians)
1964 We Wish You the Merriest / Go Tell It On the Mountain (con Bing Crosby y Fred Waring & His Pennsylvanians)
1964 Somewhere in Your Heart / Emily
1965 Anytime at All / Available
1965 Tell Her (You Love Her Each Day) / Here’s to the Losers
1965 Forget Domani / I Can’t Believe I’m Losing You
1965 When Somebody Loves You / When I’m Not Near the Girl I Love
1965 Ev’rybody Has the Right to Be Wrong! / I’ll Only Miss Her When I Think of Her
1965 It Was a Very Good Year / Moment To Moment
1966 Strangers in the Night / Oh, You Crazy Moon
1966 Summer Wind / You Make Me Feel So Young (con Count Basie & His Orchestra (directo))
1966 That’s Life / September of My Years
1967 Somethin’ Stupid (con Nancy Sinatra) / Give Her Love
1967 The World We Knew (Over and Over) / You Are There
1967 This Town / This is My Love
1968 I Can’t Believe I’m Losing You / How Old Am I?
1968 Cycles / My Way of Life
1968 Whatever Happened to Christmas / I Wouldn’t Trade Christmas (con Frank Sinatra, Jr., Nancy Sinatra y Tina Sinatra)
1969 Rain in My Heart / Star!
1969 My Way / Blue Lace
1969 Love’s Been Good to Me / A Man Alone
1969 Goin’ Out of My Head / Forget to Remember
1969 I Would Be In Love (Anyway) / Watertown
1969 What’s Now Is Now / The Train
1970 Lady Day / Song of the Sabiá
1970 Feelin’ Kinda Sunday (con Nancy Sinatra) / Kids (por Nancy Sinatra)
1970 Something / Bein’ Green
1971 Life’s a Trippy Thing (con Nancy Sinatra) / I’m Not Afraid
1971 I Will Drink The Wine / Sunrise In The Morning
1973 Let Me Try Again / Send in the Clowns
1973 You Will be My Music / Winners
1974 Bad, Bad Leroy Brown / I’m Gonna Make It All The Way
1974 You Turned My World Around / Satisfy Me One More Time
1975 Anytime (I’ll Be There) / The Hurt Doesn’t Go Away
1975 I Believe I’m Gonna Love You / The Only Couple on the Floor
1975 A Baby Just Like You / Christmas Mem’ries
1976 The Saddest Thing of All / Empty Tables
1976 I Sing the Songs (I Write the Songs) / Empty Tables
1976 Stargazer / The Best I Ever Had (con Sam Butera)
1976 Dry Your Eyes / Like a Sad Song
1976 I Love My Wife / Send in the Clowns
1977 Night and Day (disco version) / Everybody Ought to Be in Love
1980 Theme from ‘New York, New York’ / That’s What God Looks Like to Me
1980 You and Me (We Wanted It All) / I’ve Been There!
1981 Say Hello / Good Thing Going (Going Gone)
1983 Here’s to the Band / It’s Sunday (con Tony Mottola)
1983 To Love a Child / That’s What God Looks Like to Me
1984 Teach Me Tonight / The Best of Everything (Qwest)
1984 Mack the Knife / It’s All Right with Me (Qwest)
1984 L.A. Is My Lady / Until the Real Thing Comes Along (Qwest)
1993 I’ve Got You Under My Skin (con Bono) (Island Records)

Discos originales
Columbia
1946: The Voice Of Frank Sinatra, con arreglos de Alex Stordahl.
1947: Songs By Sinatra, Volume 1, con arreglos de Alex Stordahl.
1949: Frankly Sentimental, con arreglos de Alex Stordahl.
1950: Dedicated To You, con arreglos de Alex Stordahl.
1950: Swing And Dance With Frank Sinatra, con arreglos de George Siravo.

Capitol
1954: Songs for Young Lovers. Arreglos de Nelson Riddle y George Siravo.
1954: Swing Easy. Arreglos de Nelson Riddle y Heinie Beau.
1955: In The Wee Small Hours. Arreglos de Nelson Riddle.
1956: Songs For Swingin’ Lovers. Arreglos de Nelson Riddle.
1957: Close To You. Arreglos de Nelson Riddle.
1957: A Swingin’ Affair. Arreglos de Nelson Riddle.
1957: Where Are You?. Arreglos de Gordon Jenkins.
1958: Come Fly With Me. Arreglos de Billy May.
1958: Frank Sinatra Sings For Only The Lonely. Arreglos de Nelson Riddle.
1959: Come Dance With Me!. Arreglos de Billy May.
1959: No One Cares. Arreglos de Gordon Jenkins.
1960: Nice ‘N’ Easy. Dirección orquestal y arreglos de Nelson Riddle.
1961: Sinatra’s Swingin’ Session!!! And More. Dirección orquestal y arreglos de Nelson Riddle.
1961: Come Swing With Me. Arreglos de Billy May y Heinie Beau.
1962. Point Of No Return. Arreglos de Alex Stordahl y Henie Beau.
1993: Duets.
1994: Duets II

Reprise Records
1961: Ring-a-ding ding!. Dirección orquestal y arreglos de Johnny Mandel, y arreglos de Skip Martin y Dick Reynolds.
1961: Sinatra Swings / Swing Along With Me. Con arreglos de Billy May.
1961: I Remember Tommy. Con arreglos de Sy Oliver.
1962: Sinatra And Strings. Con arreglos de Don Costa.
1962: Sinatra And Swingin’ Brass. Con arreglos de Neal Hefti.
1962: Sinatra Sings Great Songs From Great Britain. Con arreglos de Robert Farnon.
1962: Sinatra-Basie. Con arreglos de Neal Hefti.
1962: All Alone. Con arreglos y dirección orquestal de Gordon Jenkins.
1963: The Concert Sinatra. Con arreglos y dirección orquestal de Nelson Riddle.
1963: Sinatra’s Sinatra. Con arreglos de Nelson Riddle.
1964: Frank Sinatra Sings Days Of Wine And Roses, Moon River And Other Academy Award Winners. Con arreglos de Nelson Riddle.
1964: It Might As Well Be Swing. Con arreglos de Quincy Jones.
1964: 12 Songs of Christmas. Con Bing Crosby, y “Fred Warring and his Pennsylvanians”.
1964: Softly, as I Leave You. Con arreglos de Ernie Freeman, Billy May, Nelson Riddle y Marty Paich
1965: Sinatra ’65: The Singer Today. Álbum compilatorio.
1965: Septembers of My Years. Con arreglos y dirección orquestal de Gordon Jenkins.
1965: My Kind of Broadway. Con arreglos de Quincy Jones, Nelson Riddle, Sy Oliver, Billy May, Don Costa y Neal Hefti
1965: A Man And His Music.
1966: Moonlight Sinatra. Con arreglos de Nelson Riddle.
1966: Strangers In The Night. Con arreglos de Nelson Riddle y Ernie Freeman.
1966: That’s Life. Con arreglos de Ernie Freeman.
1967: Francis Albert Sinatra & Antonio Carlos Jobim. Con arreglos de Claus Ogerman.
1967: The World We Knew.
1968: Francis A. And Edward K. Con arreglos de Billy May.
1968: Cycles. Con arreglos y producción de Don Costa, y dirección orquestal de Bill Miller.
1969: My Way. Con arreglos de Don Costa.
1969: A Man Alone. Con arreglos de Don Costa.
1970: Watertown. Con arreglos de Joe Scott y Charles Callelo.
1971: Sinatra and Company. Con arreglos de Eumir Deodato y Don Costa.
1973: Ol’ Blue Eyes Is Back. Con arreglos de Gordon Jenkins y Don Costa.
1974: Some Nice Things I’ve Missed. Con arreglos de Don Costa y Gordon Jenkins, y producción de Don Costa, Jimmy Bowen y Sonny Burke.
1980: Trilogy. Con arreglos y dirección orquestal de Billy May, Don Costa y Gordon Jenkins; y la producción de Sonny Burke.
1981: She Shot Me Down.
1984: L.A. Is My Lady.

Álbumes grabados en Vivo
1963 Sinatra at the Sands
1974 The Main Event – Live
1994 Sinatra & Sextet: Live in Paris
1995 Sinatra 80th: Live in Concert
1997 With Red Norvo Quintet: Live in Australia, 1959
1999 Sinatra ’57 in Concert
2005 Live from Las Vegas
2006 Vegas
2008 Frank Sinatra: The Greatest Concerts
2009 New York
2009 Live at The Meadowlands
2010 Frank Sinatra: Concert Collection
2011 Best of Vegas
2014 London
2015 Sinatra: All Or Nothing At All
2015 Selections From A Voice On Air (1935 – 1955)
2016 World On A String

Álbumes conducidos por Sinatra
1946 Frank Sinatra Conducts The Music Of Alec Wilder
1956 Frank Sinatra Conducts Tone Poems of Color
1957 The Man I Love (Sung by Peggy Lee, arranged by Nelson Riddle)
1958 Sleep Warm (Sung by Dean Martin)
1962 Frank Sinatra Conducts Music From Pictures And Plays
1982 Syms by Sinatra (Sung by Sylvia Syms)
1983 Whats New? (with trumpeter Charles Turner)

Los álbumes de conciertos en vivo de Rat Pack
1993 Frank Sinatra, Dean Martin, Sammy Davis Jr. at Villa Venice, Chicago – Live 1962
1999 Frank, Sammy & Dean: The Summit in Concert
2001 The Rat Pack Live at the Sands
2002 Ratpack: From Vegas to St. Louis
2002 Christmas with the Rat Pack
2003 The Ultimate Rat Pack Collection: Live & Swingin’

Box sets y colecciones
1979 Sinatra-Jobim Sessions
1988 Screen Sinatra
1990 The Reprise Collection
1990 The Capitol Years
1992 Concepts
1993 The Columbia Years 1943-1952: The Complete Recordings
1994 The Song Is You (complete Sinatra-Dorsey)
1995 The Complete Reprise Studio Recordings
1996 The Complete Capitol Singles Collection
1998 The Best of the Columbia Years: 1943-1952
1998 The Columbia Years 1943-1952: The V-Discs
1998 Frank Sinatra & the Tommy Dorsey Orchestra
1998 The Capitol Years
2002 Frank Sinatra in Hollywood 1940-1964
2003 The Real Complete Columbia Years V-Discs
2004 The Christmas Collecton
2006 Vegas
2008 Nothing But The Best
2008 Romance: Songs From The Heart
2009 Christmas With Sinatra And Friends
2009 New York
2009 Seduction Sinatra, Sings of love
2014 Sinatra, With Love
2014 London
2015 Selections From A Voice On Air (1935 – 1955)
2015 Ultimate Sinatra
2015 Ultimate Sinatra: The Centennial Collection
2016 World On A String
2017 Baby Blue Eyes