Hollywood loves a good behind-the-scenes tale, so it’s fitting that the Oscars have rewarded a number of actors for playing… well, actors. Though it may seem like an obvious and easy role given their own career, portraying an actor on screen offers a unique set of challenges for thespians. Not only do they need to make the audience believe their character as a real person, as all actors do, but they must do this while calling attention to their acting process, by virtue of their character’s profession. It can be a challenging task to keep their acting relatively invisible, and some actors have managed great success in this realm.

In the earlier days, behind-the-scenes films typically focused on fictional characters and productions. Around the 1960s—when Hollywood had built up a couple of generations’ worth of nostalgia for its most fascinating early stars—they began to shift towards telling stories about real players from Hollywood’s history, and the Oscars reflect that change accordingly. It’s also worth noting that actors playing real-life performers, instead of fictional, are additionally tasked with portraying a figure that is likely already familiar to the audience. This risks the danger of either going too far into caricature, or, on the other side, having an audience lose interest because some element of the performance wasn’t exactly perfect—be it the look, the manner, or even the accent.

Many actors have been recognized by the Academy in both categories, playing both real and fictional movie actors. Below, I’ve collected some of best, most interesting, and most memorable moments in Oscar history for these specifically challenging and unique roles.

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A Star is Born (1937)
Actors: Fredric March and Janet Gaynor
Characters: Norman Maine and Vicki Lester, fictional movie couple (supposedly based partially on Barbara Stanwyck and Frank Fay) navigating the tumultuous Hollywood scene.
Award Status: Best Actor (nominated) and Best Actress (nominated)

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Singin’ in the Rain (1937)
Actress: Jean Hagen
Character: Lina Lamont, the selfish, adorable actress intent on using talented nobody Kathy Selden as a stepping stone to her continued success.
Award Status: Best Supporting Actress (nominated)

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Sunset Boulevard (1951)
Actress: Gloria Swanson
Character: Norma Desmond, fading star of the fictional silent screen who manically soaks up attention from live-in biographer Joe Gillis.
Award Status: Best Actress (nominated)

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All About Eve (1951)
Actresses: Anne Baxter and Bette Davis
Characters: Eve Harrington and Margo Channing, dueling divas caught up in the pursuit of fame, obsession, and ambition.
Award Status: Best Actress (nominated) and Best Actress (nominated)

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A Star is Born (1954)
Actors: James Mason and Judy Garland
Characters: Norman Maine and Vicki Lester, fictional movie couple once again attempting to navigate the murky waters of Hollywood.
Award Status: Best Actor (nominated) and Best Actress (nominated)

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What Ever Happened to Baby Jane? (1962)
Actress: Bette Davis
Character: Baby Jane Hudson, twisted former child star now determined to make her invalid sister’s life a living hell.
Award Status: Best Actress (nominated)

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Funny Girl (1968)
Actress: Barbra Streisand
Character: Fanny Brice, the real-life vaudeville sensation and comedian who also appeared in films like Ziegfeld Follies.
Award Status: Best Actress (won)

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Frances (1983)
Actress: Jessica Lange
Character: Frances Farmer, the strong-willed actress who starred in a few pictures for Paramount in the ’30s before getting involuntarily committed to a mental hospital in 1943.
Award Status: Best Actress (nominated)

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Chaplin (1993)
Actor: Robert Downey, Jr.
Character: Charlie Chaplin, the writer, director, producer, and actor of some of silent (and sound) film’s most enduring masterpieces.
Award Status: Best Actor (nominated)

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Ed Wood (1993)
Actor: Martin Landau
Character: Bela Lugosi, horror movie icon known for his portrayal of Dracula, later often typecast due to his heavy Hungarian accent.
Award Status: Best Supporting Actor (won)

Pulp Fiction

Pulp Fiction (1994)
Actress: Uma Thurman
Character: Mia Wallace, a fictional actress who was the star of the TV show pilot, Fox Force Five.
Award Status: Best Supporting Actress (nominated)

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Shadow of the Vampire (2000)
Actor: Willem Dafoe
Character: Max Shreck, the actor most famous for his dedicated and perhaps obsessive performance as the creature in Nosferatu.
Award Status: Best Supporting Actor (nominated)

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The Aviator (2005)
Actress: Cate Blanchett
Character: Katharine Hepburn, the vivacious, Oscar-winning actress  and prime object of entrepreneur Howard Hughes’ affections in the late 1930s.
Award Status: Best Supporting Actress (won)

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Venus (2006)
Actor: Peter O’Toole
Character: Maurice, a fictional, artistic-minded actor who develops a questionable friendship with a young woman late in his life.
Award Status: Best Actor (nominated)

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The Artist (2011)
Actors: Jean Dujardin and Berenice Bejo
Characters: George Valentin and Peppy Miller, two silent film actors working in Hollywood around the cusp of sound age (again).
Award Status: Best Actor (won) and Best Supporting Actress (nominated)

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My Week with Marilyn (2012)
Actors: Michelle Williams and Kenneth Branagh
Characters: Marilyn Monroe and Laurence Olivier, the ultimate blonde bombshell and the proper Shakespearean actor, who co-starred in The Prince and the Showgirl (1957).
Award Status: Best Actress (nominated) and Best Supporting Actor (nominated)

Did I miss any of your favorites? Or were your favorites outrageously not ever nominated? Should any of the nominated actors have actually won? Or did any of the winning actors earn something they shouldn’t have? Share your thoughts in the comments!

This is part of the 31 Days of Oscar blogathon, hosted by Kellee of Outspoken and Freckled, Paula of Paula’s Cinema Club and Aurora of Once Upon a Screen. To find out more info, visit the blogathon home page. All my Oscar entries are/will be tagged under 31 Days of Oscar.

11 Replies to “31 Days of Oscar: Actors Playing Actors

  1. The performances you highlighted show that the role of an actor is one that many performers respond to with everything that is in them. Swanson as Desmond is one I find endlessly intriguing. For a while after I first saw Downey Jr. as Chaplin, I kept on seeing him even when I was watching the real deal.

    Two actors/one actor: James Cagney’s portrayals of George M. Cohan and Lon Chaney. “Yankee Doodle Dandy” is a total winner. The script for “Man of a Thousand Faces” doesn’t really do Chaney justice, but Cagney’s performance certainly does.

    Tops of all time: Ronald Colman’s Oscar winning performance in “A Double Life” as an actor who sadly loses himself in the roles he plays.

    1. Ha, one of the first Google image results for “Charlie Chaplin” is actually RDJ’s version, which kept throwing me off trying to put together the photos for this.

      Cagney and Colman are fantastic additions!

  2. Wonderful! Patricia reme,bered Cagney and Colman well, both have magnificent performances! And it’s great you put the first version of A Star is Born, it’s my favorite film.
    In Show People, from 1968, Marion Davies plays a wannabe actress in Hollywood, also.
    One thing: Barbra Streisand won an Oscar for Funny Girl, tied with Kate Hepburn.
    Don’t forget to read my contribution to the blogathon!
    Kisses! :)

    1. Oops, yes she did! You know, I couldn’t find a good existing list of all this, so for the most part it was just me typing it all out, haha. Thanks for the catch!

      I think I’ll have to do a second post focusing on the best portrayals of specifically stage actors, as well as great performances from people who didn’t actually get nominated for an Oscar. I just watched Show People and Marion was adorable—I loved her “cameo” as herself :)

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