Doctor Dolittle wins two Academy Awards 1968

Twentieth Century Fox Studio's box office bomb Doctor Doolittle was nominated for nine Academy Awards despite its poor critical reception and low box-office returns. Because of its lousy performance, the studio mounted a huge Oscar campaign, where they wined and dined members of the Academy.  It resulted in the movie being nominated for Best Picture.  At a 27% rating from Rotten Tomatoes, it is the poorest reviewed movie to be nominated for Best Picture at the 40th annual ceremony held April 10, 1968.

It was also nominated for Best Art Direction, Best Cinematography, Best Film Editing, Best Music Score, Best Original Song Score or Adaption Score. Best Song, Best Sound, and Best Special Visual Effects.

It won Best Song for Talk to the Animals, and Best Special Visual Effects for L. B. Abbot.

In the Heat of the Night was the big winner that night with five wins: Best Picture, Best Actor for Rod Steiger, Best Writing, Best Sound, and Best Editing.

Rita Moreno wins Best Supporting Actress Academy Award 1961

At what would be the beginning of a stellar career with multiple awards, Rita Moreno won the Academy Award for Best Supporting Actress for her performance in West Side Story at the 34th annual ceremony held April 9, 1962. 

West Side Story was the big winner of the evening, winning ten awards out of eleven nominations.  Besides Moreno's win, it won:

Best Motion Picture

Best Directing for Robert Wise and Jerome Robbins

Best Supporting Actor for George Chakiris

Best Music (Scoring of a Musical Picture) for Saul Chaplin, Johnny Green, Sid Ramin, and Irwin Kostal

Best Sound for Gordon Sawyer and Fred Hynes

Best Art Direction (Color) for Boris Leven and Victor Gangelin

Best Cinematography (Color) for Daniel Fapp

Best Costume Design (Color) for Irene Sharaff, beating Edith Head.

Best Film Editing for Thomas Stanford

West Side Story's only loss was for Best Writing (Screenplay-Based on Material from Another Medium).

Breakfast at Tiffany's was nominated for five awards but won only two, both going to Henry Mancini: Best Music (Music Score of a Dramatic or Comedy Picture) and Best Music (Song) for Moon River with Johnny Mercer who wrote the lyrics. 

"Rebecca" "Pinocchio" each win two Academy Awards 1941

Alfred Hitchcock's Rebecca was nominated for eleven Academy Awards but took home only two at the annual celebration held February 27, 1941.  Rebecca won Best Picture, the award going to producer David O. Selznick.  It also won Best Cinematography (Black and White) for George Barnes.  It was the only Alfred Hitchcock movie to win Best Picture.  

Hitchcock was nominated for Best Directing. Laurence Olivier was nominated for Best Actor for his role as Maximilian de Winter.  Joan Fontaine was nominated for Best Actress for her portrayal as Mrs.de Winter. Dame Judith Anderson was nominated for Best Actress in a Supporting Role as Mrs. Danvers.  She should have won.

Rebecca was nominated for Best Writing (Screenplay), Best Art Direction (Black-and-White), Best Film Editing, Best Special Effects, and Best Music (Original Score).

Walt Disney's Pinocchio was nominated for two Academy Awards and won both: Best Music (Original Score) for Leigh Harline, Paul Smith, and Ned Washington; and Best Music (Song) for When You Wish Upon a Star, music by Leigh Harline, and lyrics Ned Washington.

"The Little Mermaid" wins two Grammy Awards 1991

Composer Alan Menken and lyricist Howard Ashman took home two Grammy Awards for their music for Disney's The Little Mermaid at the 33rd annual ceremony, held February 20, 1991.

They won for Best Recording For Children for the soundtrack, and they won Best Song Written Specifically for a Motion Picture or Television for Under the Sea.

WALL-E wins two Grammy Awards 2009

My hero WALL-E won two Grammy Awards during the 51st annual celebration February 8, 2009.  Actually Peter Gabriel got the trophies.  The first for Best Song Written for Motion Picture, Television or Other Visual Media for the song Down to Earth.

The second award was for Best Instrumental Arrangement for Define Dancing, arranged by Peter Gabriel and Thomas Newman.  Newman was also nominated for Best Score Soundtrack Album for Motion Picture, Television or Other Visual Media, but lost to The Dark Night.

John Williams won a Grammy for Best Instrumental Composition for The Adventures of Mutt from Indiana Jones and the Kingdom of the Crystal Skull.  What was his total tally at that time?

One of my favorites from Tom Petty & The Heartbreakers, Runnin' Down a Dream, won Best Long Form Music Video. 

The lovely Natalie Cole won Best Traditional Pop Vocal Album for Still Unforgettable, another compilation of her performing her father's songs.