| 1958 – 1st Annual Grammy Awards | ||
| Best vocal performance, Male | Perry Como | Catch a Falling Star |
| Best vocal performance, Female | Ella Fitzgerald | Ella Sings Irving Berlin |
| Album of the Year | Henry Mancini | Peter Gunn |
| Record & Song of the Year | Domenico Modugno | Nel Blu Di Pinto Di Blu |
| Unusual Feature: Cartoon characters Alvin and the Chipmunks win one of the first Grammy awards. | ||
| 1959 – 2nd Annual Grammy Awards | ||
| Record of the year | Bobby Darin | Mack the Knife |
| Album of the year | Frank Sinatra | Come Dance With Me |
| Best New artist | Bobby Darin | |
| Song of the year | Jimmy Driftwood | The Battle of New Orleans |
| Best vocal performance – female | Ella Fitzgerald | But Not For Me |
| Best vocal performance – male | Frank Sinatra | Come Dance With Me |
| Unusual Feature: Frank Sinatra wins three Grammys. | ||
| 1960 – 3rd Annual Grammy Awards | ||
| Record of the year | Percy Faith | Theme From a Summer Place |
| Song of the year | Ernest Gold | Theme From Exodus |
| Album of the year | Bob Newhart | The Button-down Mind Strikes Back |
| Best new artist | Bob Newhart | The Button-down Mind Strikes Back |
| Unusual Feature: Comedian Bob Newhart wins 3 Grammys. | ||
| 1961 – 4th Annual Grammy Awards | ||
| Record of the year | Henry Mancini | Moon River |
| Song of the year | Johnny Mercer & H. Mancini | Moon River |
| Album of the Year | Judy Garland | Judy at Carnegie Hall |
| Best Solo Vocal performance, female | Judy Garland | Judy at Carnegie Hall |
| Best Solo Vocal performance, male | Jack Jones | Lollipops and Roses |
| Best new artist | Peter Nero | |
| Unusual Feature: Judy Garland wins 2 Grammys for her performance at Carnegie Hall. | ||
| 1962 – 5th Annual Grammy Awards | ||
| Record of the year | Tony Bennett | I Left My Heart in San Francisco |
| Song of the year | Bricusse & Newley (writers) | What Kind of Fool Am I |
| Song of the year | Bricusse & Newley (writers) | What Kind of Fool Am I |
| Best solo vocal performance – male | Tony Bennett | I Left My Heart in San Francisco |
| Best Solo vocal performance, female | Ella Fitzgerald | Ella Swings w/ Nelson Riddle |
| Best new artist | Robert Goulet | |
| 1963 – 6th Annual Grammy Awards | ||
| Record of the year | Henry Mancini | Days of Wine and Roses |
| Song of the year | Henry Mancini | Days of Wine and Roses |
| Album of the year | Barbra Streisand | The Barbra Streisand Album |
| Best Vocal performance – female | Barbra Streisand | The Barbra Streisand Album |
| Best vocal performance – male | Jack Jones | Wives and Lovers |
| Unusual Feature: Leonard Bernstein wins third consecutive Grammy for children. The Singing Nun picks up award for "Dominique" | ||
| 1964 – 7th Annual Grammy Awards | ||
| Best new artist | The Beatles | |
| Album of the year | Stan Getz/Joao Gilberto | Getz/Gilberto |
| Record of the year | Astrud Gilberto/Stan Getz | The Girl from Ipanema |
| Best vocal performance – male | Louis Armstrong | Hello Dolly! |
| Best vocal performance, female | Barbra Streisand | People |
| Unusual Feature: The Beatles win the first two of their many Grammys, but Roger Miller was the night's big winner with five. | ||
| 1965 – 8th Annual Grammy Awards | ||
| Record of the year | Herb Alpert & Tijuana Brass | A Taste of Honey |
| Album of the year | Frank Sinatra | September of My Years |
| Best new artist | Tom Jones | |
| Best vocal performance, male | Frank Sinatra | It Was A Very Good Year |
| Best vocal performance, female | Barbra Streisand | My Name is Barbra |
| Unusual Feature :Roger Miller wins six Grammys, one more than he took home the previous year. | ||
| 1966 – 9th Annual Grammy Awards | ||
| Record of the year | Frank Sinatra | Strangers in the Night |
| Album of the year | Frank Sinatra | Sinatra: A Man and His Music |
| Song of the year | Lennon & McCartney | Michelle |
| Best vocal performance, male | Frank Sinatra | Strangers in the Night |
| Best vocal performance, female | Eydie Gorme | If He Walked Into My Life |
| Unusual Feature :CBS newsman Edward R. Murrow wins a Grammy for "Edward R. Murrow – A Reporter Rembers, Vol 1. The War Years" | ||
| 1967 – 10th Annual Grammy Awards | ||
| Record of the year | 5th Dimension | Up, Up and Away |
| Song of the year | 5th Dimension | Up, Up and Away |
| Album of the year | The Beatles | Sgt Pepper's Lonely Hearts Club Band |
| Best new artist | Bobbie Gentry | |
| Best vocal performance, Male | Glen Campbell | Gentle On My Mind |
| Best vocal performance, female | Bobbie Gentry | Ode to Billie Joe |
| Unusual Feature: Elvis wins his first Grammy. | ||
| 1968 – 11th Annual Grammy Awards | ||
| Album of the year | Glen Campbell | By The Time I Get To Phoenix |
| Best new artist | Jose Feliciano | |
| Record of the year | Simon and Garfunkel | Mrs. Robinson |
| Song of the year | Bobby Russell/Writer | Little Green Apples |
| Unusual Feature: Otis Redding wins posthumous Grammys. | ||
| 1969 – 12th Annual Grammy Awards | ||
| Record of the year | 5th Dimension | Aquarius/Let the Sunshine In |
| Album of the year | Blood, Sweat and Tears | Blood, Sweat and Tears |
| Song of the year | Joe South | Games People Play |
| Best new artist | Crosby, Stills and Nash | |
| Best contemporary vocal, female | Peggy Lee | Is That All There IS |
| Best contemporary vocal, male | Harry Nilsson | Everybody's Talkin' |
| 1970 – 13th Annual Grammy Awards | ||
| Song of the year | Simon and Garfunkel | Bridge Over Troubled Waters |
| Record of the Year | Simon and Garfunkel | Bridge Over Troubled Waters |
| Album of the Year | Simon and Garfunkel | Bridge Over Troubled Waters |
| Best Contemporary vocal, male | Ray Stevens | Everything Is Beautiful |
| Best contemporary vocal, female | Dionne Warwick | I'll Never Fall In Love Again |
| Best new artist | The Carpenters | |
| 1971 – 14th Annual Grammy Awards | ||
| Record of the year | Carol King | It's Too Late |
| Album of the year | Carol King | Tapestry |
| Song of the year | Carol King | You've Got A Friend |
| Best pop vocal, female | Carol King | Tapestry |
| Best pop vocal, male | James Taylor | You've Got a Friend |
| Best new artist | Carly Simon | |
| 1972 – 15th Annual Grammy Awards | ||
| Best new artist | America | |
| Album of the year | George Harrison, Phil Spector | Concert for Bangladesh |
| Record of the year | Roberta Flack | First Time Ever I Saw Your Face |
| Song of the year | Roberta Flack | First Time Ever I Saw Your Face |
| Unusual Feature: George Harrison wins a Grammy after Beatles' breakup. | ||
| 1973 – 16th Annual Grammy Awards | ||
| Record of the year | Roberta Flack | Killing Me Softly With His Song |
| Song of the year | Roberta Flack | Killing Me Softly With His Song |
| Album of the year | Stevie Wonder | Innervisions |
| Best new artist | Bette Midler | |
| Best pop vocal, male | Stevie Wonder | You Are The Sunshine Of My Life |
| Best pop vocal, female | Roberta Flack | Killing Me Softly With His Song |
| 1974 – 17th Annual Grammy Awards | ||
| Song of the year | Barbra Streisand | The Way We Were |
| Record of the year | Olivia Newton-John | I Honestly Love You |
| Album of the year | Stevie Wonder | Fulfillingness' First Finale |
| Best new artist | Marvin Hamlisch | |
| Best pop vocal, female | Olivia Newton-John | I Honestly Love You |
| Best pop vocal, male | Stevie Wonder | Fulfillingness' First Finale |
| 1975 – 18th Annual Grammy Awards | ||
| Record of the year | Captain & Tennille | Love Will Keep Us Together |
| Album of the year | Paul Simon | Still Crazy After All These Years |
| Song of the year | Judy Collins | Send In The Clowns |
| Best new artist | Natalie Cole | |
| Best pop vocal, female | Janis Ian | At Seventeen |
| Best pop vocal, male | Paul Simon | Still Crazy After All These Years |
| 1976 – 19th Annual Grammy Awards | ||
| Album of the year | Stevie Wonder | Songs In the Key of Life |
| Record of the year | George Benson | This Masquerade |
| Best pop vocal, female | Linda Ronstadt | Hasten Down The Wind |
| Best new artist | Starland Vocal Band | Afternoon Delight |
| Best pop vocal, male | Stevie Wonder | Songs In the Key of Life |
| 1977 – 20th Annual Grammy Awards | ||
| Best new artist | Debby Boone | |
| Record of the year | The Eagles | Hotel California |
| Album of the year | Fleetwood Mac | Rumors |
| Best pop vocal, female | Barbra Streisand | Evergreen |
| Best pop vocal, male | James Taylor | Handy Man |
| 1978 – 21st Annual Grammy Awards | ||
| Album of the year | Bee Gees | Saturday Night Fever |
| Song of the Year | Billy Joel | Just the Way You Are |
| Best pop vocal, male | Barry Manilow | Copacabana |
| Best pop vocal, female | Anne Murray | You Needed Me |
| Unusual Feature: Disco is king of the evening. | ||
| 1979 –22nd Annual Grammy Awards | ||
| Album of the year | Billy Joel | 52nd Street |
| Song of the year | McDonald & Loggins | What A Fool Believes |
| Best new artist | Ricky Lee Jones | |
| Best pop vocal, female | Dionne Warwick | I'll Never Love This Way Again |
| Best pop vocal, male | Billy Joel | 52nd Street |
| 1980 – 23rd Annual Grammy Awards | ||
| Record of the year | Christopher Cross | Sailing |
| Album of the year | Christopher Cross | Sailing |
| Song of the year | Christopher Cross | Sailing |
| Best new artist | Christopher Cross | |
| Best pop vocal, female | Bette Midler | The Rose |
| 1981 – 24th Annual Grammy Awards | ||
| Record of the year | Kim Carnes | Bette Davis Eyes |
| Album of year | John Lennon & Yoko Ono | Double Fantasy |
| Best new artist | Sheena Easton | |
| Best pop vocal, female | Lena Horne | The Lady & Her Music, Live On Broadway |
| Best pop vocal, male | Al Jarreau | Breakin' Away |
| Unusual feature : First Grammy for music videos is given out. | ||
| 1982 – 25th Annual Grammy Awards | ||
| Song of the year | Carson, James & Christopher | Always On My Mind |
| Record of the year | Toto | Rosanna |
| Album of the year | Toto | Toto IV |
| Best pop vocal, female | Melissa Manchester | You Should Hear How She Talks About You |
| Best pop vocal, male | Lionel Richie | Truly |
| Best new artist | Men At Work | |
| 1983 – 26th Annual Grammy Awards | ||
| Record of the year | Michael Jackson | Beat It |
| Album of the year | Michael Jackson | Thriller |
| Song of the year | Sting/Police | Every Breath You Take |
| Best pop vocal, male | Michael Jackson | Thriller |
| Best pop vocal, female | Irene Cara | Flashdance…What A Feeling |
| Best new artist | Culture Club | |
| 1984 – 27th Annual Grammy Awards | ||
| Record of the year | Tina Turner | What's Love Got To Do With It |
| Song of the year | Britten & Lyle | What's Love Got To Do With It |
| Album of the year | Lionel Richie | Can't Slow Down |
| Best pop vocal, male | Phil Collins | Against All Odds |
| Best Latin pop performance | Placido Domingo | Always In My Heart |
| Best new artist | Cyndi Lauper | |
| Best pop vocal, female | Tina Turner | What's Love Got To Do With It |
| 1985 – 28th Annual Grammy Awards | ||
| Album of the year | Phil Collins | No Jacket Required |
| Best pop vocal, female | Whitney Houston | Saving All My Love For You |
| Song of the year | Michael Jackson & Lionel Richie | We Are The World |
| Record of the year | Quincy Jones | We Are The World |
| Best new artist | Sade | |
| Unusual Feature: First Grammy is given for Best Polka Recording. | ||
| 1986 – 29th Annual Grammy Awards | ||
| Song of the year | Carole Bayer Sager, Burt Bacharach | That's What Friends Are For |
| Album of the year | Paul Simon | Graceland |
| Record of the year | Steve Winwood | Higher Love |
| Best pop vocal, female | Barbra Streisand | The Broadway Album |
| Best pop vocal, male | Steve Winwood | Higher Love |
| Best new artist | Bruce Hornsby and the Range | |
| Unusual Feature: New Age Music gets its own category. | ||
| 1987 – 30th Annual Grammy Awards | ||
| Album of the year | U2 | The Joshua Tree |
| Song of the year | Mann, Weil & Horner(writers) | Somewhere Out There |
| Best pop vocal, female | Whitney Houston | I Wanna Dance With Somebody |
| Record of the year | Paul Simon | Graceland |
| Best pop vocal, male | Sting | Bring On The Night |
| Best new artist | Jody Watley | |
| 1988 – 31st Annual Grammy Awards | ||
| Album of the year | George Michael | Faith |
| Record of the year | Bobby McFerrin | Don't Worry, Be Happy |
| Song of the year | Bobby McFerrin | Don't Worry, Be Happy |
| Best pop vocal, male | Bobby McFerrin | Don't Worry, Be Happy |
| Best pop vocal, female | Tracy Chapman | Fast Car |
| Best new artist | Tracy Chapman | |
| Unusual Feature: First Grammy is awarded for Rap music | ||
| 1989 – 32nd Annual Grammy Awards | ||
| Best pop vocal, male | Michael Bolton | How Am I Supposed To Live Without You |
| Song of the year | Larry Henly & Jeff Silbar (writers) | Wind Beneath My Wings |
| Album of the year | Bonnie Raitt | Nick of Time |
| Best pop vocal, female | Bonnie Raitt | Nick of Time |
| 1990 – 33rd Annual Grammy Awards | ||
| Record of the year | Phil Collins | Another Day In Paradise |
| Song of the year | Julie Gold (writer) | From a Distance |
| Album of the year | Quincy Jones | Back on the Block |
| Best pop vocal, male | Roy Orbison | Pretty Woman |
| Best pop vocal, female | Mariah Carey | Vision of Love |
| Best new artist | Mariah Carey | |
| 1991 – 34th Annual Grammy Awards | ||
| Album of the year | Natalie Cole | Unforgettable |
| Record of the year | Natalie Cole | Unforgettable |
| Song of the year | Natalie Cole | Unforgettable |
| Best pop vocal, female | Bonnie Raitt | Something To Talk About |
| Best pop vocal, male | Michael Bolton | When A Man Loves A Woman |
| Best new artist | Marc Cohn | |
| 1992 – 35th Annual Grammy Awards | ||
| Best new artist | Arrested Development | |
| Record of the year | Eric Clapton | Tears in Heaven |
| Album of the year | Eric Clapton | Unplugged |
| Song of the year | Eric Clapton | Tears in Heavan |
| Best pop vocal, male | Eric Clapton | Eric Clapton nplugged |
| Best pop vocal, female | k.d. lang | Constant Craving |
| 1993 – 36th Annual Grammy Awards | ||
| Album of the year | Whitney Houston | The Bodyguard |
| Best new artist | Toni Braxton | |
| Record of the year | Whitney Houston | I Will Always Love You |
| Best pop vocal, female | Whitney Houston | I Will Always Love You |
| Best pop vocal, male | Sting | If I Ever Lose My Faith In You |
| 1994 – 37th Annual Grammy Awards | ||
| Album of the year | Tony Bennett | MTV Unplugged |
| Record of the year | Sheryl Crow | All I Wanna Do |
| Song of the year | Bruce Springsteen | Streets of Philadelphia |
| Best pop vocal, female | Sheryl Crow | All I Wanna Do |
| Best Pop vocal, male | Elton John | Can You Feel The Love Tonight |
| Best new artist | Cheryl Crow | |
| 1995 – 38th Annual Grammy Awards | ||
| Album of the year | Alanis Morissette | Jagged Little Pill |
| Song of the year | Seal | Kiss From a Rose |
| Record of the year | Seal | Kiss From a Rose |
| Best pop vocal, female | Annie Lennox | No More "I Love You's" |
| Best pop vocal, male | Seal | Kiss From a Rose |
| Best new artist | Hootie & The Blowfish | |
| 1996 – 39th Annual Grammy Awards | ||
| Record of the year | Eric Clapton | Change The World |
| Album of the year | Celine Dion | Falling Into You |
| Best pop vocal, female | Toni Braxton | Un-Break My Heart |
| Best pop vocal, male | Eric Clapman | Change The World |
| Best new artist | LeAnn Rimes | |
| 1997 – 40th Annual Grammy Awards | ||
| Best new artist | Paula Cole | |
| Record of the year | Shawn Colvin | Sunny Came Home |
| Song of the year | Shawn Colvin | Sunny Came Home |
| Best pop vocal, female | Sarah McLachlan | Building a Mystery |
| 1998 – 41st Annual Grammy Awards | ||
| Record of the year | Celine Dion | My Heart Will Go On |
| Song of the year | Celine Dion | My Heart Will Go On |
| Bets pop vocal, male | Eric Clapton | My Father's Eyes |
| Best pop vocal, female | Celine Dion | My Heart Will Go On |
| Best new artist | Lauryn Hill | |
| 1999 – 42nd Annual Grammy Awards | ||
| Album of the year | Santana | Supernatural |
| Record of the yar | Santana, Featuring Rob Thomas Smooth | |
| Best pop vocal, female | Sarah McLachlan | I Will Remember You |
| Best pop vocal, male | Sting | Brand New Day |
| Best new artist | Christina Aguilera | |
| 2000 – 43rd Annual Grammy Awards | ||
| Album of the year | Steely Dan | Two Against Nature |
| Record of the year | U2 | Beautiful Day |
| Best pop vocal, female | Macy Gray | I Try |
| Best pop vocal, male | Sting | She Walks This Earth |
| Best new artist | Shelby Lynne | |