Henry Mancini wins 5 Grammy Awards 1962

Henry Mancini won five Grammy Awards for his work on Breakfast at Tiffany's at the 4th annual ceremony, held May 29, 1962.  His composition of the soundtrack won Best Sound Track Album or Recording Score from Motion Picture or Television, and Best Performance by an Orchestra - for Other Than Dancing.  The latter award was from the Pop category?

His original song Moon River won Record of the year, Song of the Year, and Best Arrangement.

West Side Story won Best Sound Track Album or Recording of Original Cast from a Motion Picture or Television.

Ray Charles won Best Rhythm & Blues Performance for Hit the Road Jack.

The Police release "Every Breath You Take" 1983

The Police released their huge-selling Every Breath You Take May 20, 1983.  It was the biggest single in the US and Canada in 1983, and topped the Billboard Hot 100 for eight weeks, The Police's only #1 on that chart.

It won three Grammy Awards at the 26th ceremony, winning Song of the Year, Best Pop Performance by a Duo or Groups with Vocals, and Best Rock Performance by a Duo or Group with Vocal.

In 1999, BMI listed it as one of the Top 100 songs of the century. Rolling Stone magazine listed it as #84 in the 500 Greatest Songs of All Time, and #25 on the Billboard's Hot 100 All-Time Top Songs.

The 5th Dimension's "Up, Up and Away" win 6 Grammy Awards 1968

The 5th Dimension's 1967 recording of Up, Up and Away took home 6 Grammy Awards at the 10th annual ceremony held February 29, 1968.  Producers Johnny Rivers and Marc Gordon took home Record of the Year.  Jimmy Webb, songwriter, received Song of the Year.  The 5th Dimension won Best Performance by a Vocal Group, Best Performance by a Chorus, Best Contemporary Group Performance (Vocal or Instrumental), and Best Contemporary Single. 

Boris Karloff (horror movie icon) won a Grammy for Best Recording for Children, for his work on Dr. Seuss: How the Grinch Stole Christmas.

Elvis Presley won Best Sacred Performance for his recording of How Great Thou Art.

The Beatles won 4 Grammys for Sgt. Pepper's Lonely Hearts Club Band: Album of the Year; Best Album Cover, Graphic Arts; Best Contemporary Album; and Best Engineered Recording - Non-Classical. 

Celebrating Native American Heritage Month: Bill Miller, winner of 5 Native American Music Awards 1999

At the second annual Native American Music Awards ceremony, held November 6, 1999, artist Bill Miller won five awards.  He took home the awards for Song of the Year for Ghostdance, Artist of the Year, Best Male Artist,, and Songwriter of the Year.  I cannot find a complete list of awards for that year, so I do not know what the fifth award was.

Listen to his award winning song:

Simon & Garfunkel's "Bridge Over Troubled Water" wins 6 Grammys 1971

Simon & Garfunkels' mega-hit Bridge Over Troubled Water won a whopping 6 Grammy Awards at the 13th annual ceremony held March 16, 1971.  It swept the top 3: Record of the Year, Song of the Year, and Album of the Year.  It also won Best Arrangement Accompanying Vocalists Larry Knechtel and Paul Simon; Best Contemporary Song; and Best Engineered Recording, Non-Classical for Roy Halee.

Roberta Flack wins 3 Grammy Awards 1973

Roberta Flack won two Grammy Awards for her performance of The First Time Ever I Saw Your Face at the 15th annual ceremony held March 3, 1973.  She won Record of the Year with Joel Dorn, producer.  The second Grammy went to the songwriter Ewan MacColl for Song of the Year. 

The same night she won Best Pop Vocal Performance by Duo, Group or Chorus with Donnie Hathaway for their performance of Where is the Love?

Charley Pride won two Grammys.  Best Country Vocal Performance, Male for Charley Pride Sings Heart Songs; and Best Country Song for Kiss an Angel Good Morning with songwriter Ben Peters.

Billy Preston won Best Pop Instrumental Performance for Outa-Space.

"You're The Reason God Made Oklahoma" wins Song of the Year 1981

David Frizzell and Shelly West won the Academy of Country Music Award for Song of the Year for You're the Reason God Made Oklahoma, April 30, 1981.  It was featured on the soundtrack of the Clint Eastwood movie Any Which Way You Can.

Kim Carnes releases "Bette Davis Eyes" 1981

Kim Carnes released her mega-hit Bette Davis Eyes, March 10, 1981. It was the main release from her studio album Mistaken Identity.  It spent 9 non-consecutive weeks at No. 1 on the Billboard Hot 100 and was Billboard's biggest hit of 1981.

It won Grammys for Song of the Year and Record of the Year

Simon and Garfunkel release "Bridge over Troubled Water" 1970

Simon and Garfunkel released Bridge Over Troubled Water, their fifth and final album January 26, 1970.  The single of the same name was released just a few days prior. 

The album and single won seven Grammys: Album of the Year, Best Arrangement Accompanying Vocalists, Best Engineered Recording, Contemporary Song, Record of the Year, Song of the Year.  It has been certified 8 x platinum.  Rolling Stone ranked the album No. 51 on the 500 Greatest Albums of All Time, and the single as No. 48 on the 500 Greatest Songs of All Time.

The Boxer, another single from the album released in March 1969, was another success, reaching #7 on the Billboard Hot 100.  Rolling Stone ranked it No. 106 on their list of the 500 Greatest Songs of All Time.

"Unforgettable" by Nat King Cole and Natalie Cole reaches #1 1991

Natalie Cole released her Grammy-winning album Unforgettable...With Love in June 1991, a cover of her father's songs.  July 27, 1991, Unforgettable, the duet engineered with her and Nat King Cole, reached #1 on the Billboard 200. 

The single won four Grammys: Record of the Year, Traditional Pop Vocal Performance, Song of the Year and Arrangement Accompanying Vocals.

The album won Album of the Year and Best Engineered - Non-Classical.  It has been certified 7x platinum in the U.S. as of 2009.

Billy Joel wins 2 Grammys for "Just The Way You Are" 1979

My man Billy Joel won two Grammy awards for Just the Way You Are, a track from his fifth studio album, The Stranger, at the awards show on February 15, 1979.  It was his first gold single in the U.S. and it topped Billboard's Easy Listening Chart for all of January 1978.

It won for Record of the Year and Song of the Year for 1979.

According to wikipedia, Billy didn't like the song even though he wrote it and didn't want to include it on the album, but Linda Ronstadt and Phoebe Snow convinced him to include it.

We're all glad they did!