and, and, and Isabella Bootlegs by Samantha Cooper

Brooklyn has just graduated college when her mother, Tilly, makes an odd request: that Brooklyn and her father stay locked in the house with Tilly for one year. As Brooklyn investigates the murky past behind her mother’s strange paranoia, she uncovers more family mysteries than she ever could have imagined. and, and, and Isabella Bootlegs tells the story of four generations of women who, in order to move...
Brooklyn has just graduated college when her mother, Tilly, makes an odd request: that Brooklyn and her father stay locked in the house with Tilly for one year. As Brooklyn investigates the murky past behind her mother’s strange paranoia, she uncovers more family mysteries than she ever could have imagined. and, and, and Isabella Bootlegs tells the story of four generations of women who, in order to move forward, must first delve into the secrets of their lineage.
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and, and, and Isabella Bootlegs

Recommended by

  • Cheryl Bear:
    23 Jan. 2021
    “ A terrific look inside the generational trauma that binds us. Powerful and well done! ”
  • Alix Sobler:
    10 Mar. 2020
    “ A fascinating and creative structure to show how four generations of women cope with the problems of society and everyday life. Cooper seamlessly stitches together different timelines in a way that feels almost dreamlike, but also grounded in real life events and struggles. The specter of the dead hangs over the play, at the same time it manages to be very funny. ”
  • Jeffrey James Keyes:
    1 Mar. 2020
    “ and, and, and Isabella Bootlegs is a fierce play, a bubbling kettle filled with curious and flavorful tea, it's characters all building up the courage to whistle (or simmer) at any moment. Cooper's story is rich and daring, she executes complex and heartfelt storylines with crisp, simplistic precision (and some heavy, dark laughter) to orchestrate what will truly be a powerful night of theatre. You can't help but wonder about the mysteries and secrets of own family's history after taking in this excellent play. ”
View all 7 recommendations

Character Information

  • Isabella
    She/her
    Born 1894
    Can be played by:
    • Age: 
      20s, 30s, 40s, 50s
    • Race/Ethnicity: 
      Any race/ethnicity
    • Gender: 
      Female
  • Mary
    She/her
    Born 1912
    Can be played by:
    • Age: 
      20s, 30s, 40s, 50s
    • Race/Ethnicity: 
      Any race/ethnicity
    • Gender: 
      Female
  • Tilly
    She/her
    Born 1951
    Can be played by:
    • Age: 
      20s, 30s, 40s
    • Race/Ethnicity: 
      Any race/ethnicity
    • Gender: 
      Female
  • Brooklyn (BK)
    She/her or they/them
    Born 1988
    Can be played by:
    • Age: 
      Teens, 20s
    • Race/Ethnicity: 
      Any race/ethnicity
    • Gender: 
      Female, Non-binary
  • Man
    he/him
    plays OLIVER STERLING (born 1908) and FINN (born 1949)
    Can be played by:
    • Age: 
      20s, 30s, 40s
    • Race/Ethnicity: 
      Any race/ethnicity
    • Gender: 
      Male

Production History

  • Community Theater
    ,
    Macha Monkey Productions
    ,
    2015

Awards

Finalist
,
Columbia@Roundabout 2018 New Play Reading Series
,
2018