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My Sister Eileen is a 1940 play based on a series of autobiographical short stories by Ruth McKenney, originally published in The New Yorker and that were compiled into a book in 1938. It centers on two sisters from Ohio who are out to make successful careers while living in a basement apartment in the Greenwich Village section of New York City. Older, sensible Ruth aspires to be a writer, while Eileen dreams of success on the stage.

Eileen McKenney, the inspiration for the title character, and her husband, novelist and screenwriter Nathanael West, were killed in a car accident four days before the play's opening in December 1940.

The story eventually inspired many other works:

  • A 1942 film adapted from the play released by Columbia Pictures, with a cast that includes Rosalind Russell as Ruth and Janet Blair as Eileen, and, in a cameo appearance at the end, The Three Stooges.
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  • A 1946 radio play adaptation of the 1942 film with Russell and Blair reprising their roles, which was supposed to be followed by a radio series, but which never materialized.
  • The 1953 Broadway musical Wonderful Town, with music by Leonard Bernstein, is a musical stage adaptation of the play. Russell also reprised the part of Ruth from the 1942 film for the Broadway production and appeared in a broadcast of the musical on 1958.
  • A second film adaptation in 1955, this time as a musical comedy, starring Betty Garrett as Ruth and Janet Leigh as Eileen, with Jack Lemmon, Bob Fosse (who choreographed the musical numbers), and Dick York among the supporting cast.
  • A television sitcom that premiered on CBS on October 1960. It was canceled after one season.

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This stage play and its various adaptations include examples of:

  • Bolt of Divine Retribution: Wreck's girlfriend Helen bursts out angrily at him after noticing that he's done Eileen's laundry. As Helen hastens to leave with him, he exclaims, "If I thought about Eileen that way—may God strike me dead on this spot!" He raises his hand to heaven, and is stunned by a tremendous blast from the subway tunnel under construction. Ruth looks up and says, "He's everywhere, all right."
  • Bouquet Toss: When Helen and Wreck, as the newly married Mr. and Mrs. Loomis, pay Ruth and Eileen a final visit, Helen tosses the bouquet in the air just before they get going for their honeymoon, calling out, "Who's going to be next?" The bouquet is caught by the sisters' father, Walter Sherwood.
  • The Cameo: The Three Stooges show up in a last-minute cameo in the 1942 film adaptation. The central joke of that film was that the two sisters' basement Manhattan apartment is routinely invaded by all manner of hilariously outlandish pests. The final moments of the films see the Stooges (apparently employed as subway maintenance workers) literally drilling their way into the apartment from below.
  • Dance Party Ending: The 1955 film adaptation ends with the entire Greenwich Village neighbourhood and the Brazilian navy dancing the conga.
  • The Glorious War of Sisterly Rivalry: Ruth Sherwood as the smart one and her sister Eileen as the pretty one.
  • House Husband: Wreck is unemployed outside of the professional football season. While Helen works at the office, what he spends the day doing besides drinking is ironing in his shorts and doing almost anything around the house except washing, which he considers women's work. They're not actually married until the last act, however.
  • Landlord: Mr. Appopolous, who considers renting out studios to Starving Artists "merely a hobby" of his. He is more obsessed with painting and writing poetry and drama, though he has to admit that "not more than fifteen people" in the world appreciate his artistry. The basement studio he rents to Eileen and Ruth has a landscape from his "blue-green period" hanging over one of the beds.
  • Most Writers Are Writers: The aspiring young writer Ruth Sherwood is based on Ruth McKenney, who wrote the non-fictional stories which inspired the play.
  • Only Known by Their Nickname: The Wreck. His name is Ted Loomis, but nobody calls him Ted.
    Eileen: Is there anything I can do for you, Mr. Loomis?
    The Wreck: Leave out the mister—call me Wreck.
    Eileen: Wreck?
    The Wreck: That's what they called me at Georgia Tech. I'd have made All American, only I was expelled.
  • Snipe Hunt: Chic Clark, Eileen's reporter friend, tells her that the city editor of his paper may have a job lined up for her sister Ruth, who is desperately hunting for a writing job. When Ruth gets the call and hears that the city editor wants her to cover a boatload of coffee millionaires from Brazil who have just landed on a Brooklyn pier, she rushes off in great excitement after a few hurried preparations. Soon after, Chic pays an unexpected visit to Eileen, but she remains concerned about her sister and tells him she has to change for a dinner date she has lined up. He objects: "Excuse ya? After I went and fixed it to get ya alone without that eagle-eyed sister of yours around!" Eileen then realizes that Chic, not his editor, called Ruth to lead her on a wild-goose chase and turns on him angrily. As it turns out, Ruth does find a bunch of Brazilian admirals in Brooklyn, but they speak no English and follow her all the way back to her apartment.
  • Starving Artist: Ruth Sherwood, an aspiring young writer whose stories don't come back only when she can't pay the return postage, and her sister Eileen, a would-be actress. They don't get much choice in what food they eat, and have difficulty coming up with money for subway and bus fares.
  • Very Loosely Based on a True Story: The play is based on a couple of autobiographical stories (namely, "Mr. Spitzer and the Fungus" and "Beware the Brazilian Navy") by Ruth McKenney published under the same title. All the names were changed, except for Eileen and Ruth's first names, and many details of the stories were altered or simply made up.
  • Welcome to the Big City: Ruth and Eileen are just handing over their first month's rent to their landlord Mr. Appopolous when a tremendous explosion is heard from underneath—it's blasting for a new subway. Appopolous tries to tell them that they'll get used to it, but the sisters say they want their money back. He tells them: "Listen—in New York you either live, A, over a subway, or, B, where they're building a subway, or C, you don't live in New York!" After he makes a bargain with them and leaves, Eileen tells Ruth that maybe they should have tried Cleveland first. They try to get some sleep on their all too stiff beds, but are repeatedly roused by impolite forms of city life, as well as further booms from below. It doesn't help that Ruth's bed is directly under the street lamp, with no window shade to block the light.

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