OSCAR-WINNING ROMANTIC COMEDIES

SHAKESPEARE IN LOVE (1998)

Directed by John Madden

  • Best Picture
  • Best Actress, Gwyneth Paltrow
  • Best Supporting Actress, Judi Dench
  • Best Screenplay – Written Directly for the Screen, Marc Norman and Tom Stoppard
  • Best Art Direction, Art Direction: Martin Childs; Set Decoration: Jill Quertier
  • Best Costume Design, Sandy Powell
  • Best Original Musical or Comedy Score, Stephen Warbeck

AS GOOD AS IT GETS (1997)

Directed by James L. Brooks

  • Best Actor, Jack Nicholson
  • Best Actress, Helen Hunt

THE APARTMENT (1960)

Directed by Billy Wilder

  • Best Picture
  • Best Director, Billy Wilder
  • Best Story and Screenplay – Written Directly for the Screen, Billy Wilder and I. A. L.
  • Best Art Direction – Black-and-White, Alexandre Trauner and Edward G. Boyle
  • Best Film Editing, Daniel Mandel

JUNO (2007)

Directed by Jason Reitman

  • Best Original Screenplay, Diablo Cody

IT HAPPENED ONE NIGHT (1934)

Directed by Frank Capra

  • Outstanding Production, Frank Capra and Harry Cohn
  • Best Director, Frank Capra
  • Best Actor, Clark Gable
  • Best Actress, Claudette Colbert
  • Best Adaptation, Robert Riskin

JERRY MACGUIRE (1996)

Directed by Cameron Crowe

  • Best Supporting Actor, Cuba Gooding Jr.

LA LA LAND (2016)

Directed by Damien Chazelle

  • Best Director, Damien Chazelle
  • Best Actress, Emma Stone
  • Best Cinematography, Linus Sandgren
  • Best Original Score, Justin Hurwitz
  • Best Original Song, “City of Stars” by Justin Hurwitz, Benj Pasek, and Justin Paul
  • Best Production Design, Production Design: David Wasco; Set Decoration: Sandy Reynolds-Wasco

ROMAN HOLIDAY (1960)

Directed by William Wyler

  • Best Actress, Audrey Hepburn
  • Best Story, Dalton Trumbo
  • Best Costume Design – Black-and-White, Edith Head

BONUS: PUNCH-DRUNK LOVE (2002)

Directed by Paul Thomas Anderson

Didn’t win any Academy Awards but should have, and I won’t be discussing further.

A colorful promotional poster for the film 'The Apartment,' featuring the names of the stars Jack Lemmon, Shirley Maclaine, and Fred MacMurray, along with playful graphics like flowers and smiling emojis.

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