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The Hipster Sister

Music, lyrics, and book by Andy Roninson

Brooklyn, 2015. Chelsea is getting fed up with her slacker singer-songwriter sister, Jackie, and it's time she moved out.



Cast Size

1m, 2f


10 Mins Approx.




Strong Language




Family, Sisters

Target Audience

Teen (Age 14 - 18), Young Adult (Age 18 - 23), Adult


Contemporary Musical Theatre


Piano/Vocal, Bass, Guitar, Drums, Strings, Ukulele

Additional Resources

Accompaniment Tracks


33-year-old actuary Chelsea comes home to her nice Brooklyn apartment to find her 30-year-old sister Jacqueline banging pots and yell-singing, “WE’LL NEVER BE THE SAME.” On top of that, she finds that the vase her boyfriend just got her is smashed to pieces because Jacqueline knocked it over.


Frustrated, Chelsea goes to her bedroom to vent to her boyfriend Walter. Walter reminds her that she, Chelsea, was the one who invited Jacqueline to stay on their couch while she gets her life back together. Besides, Jacqueline is such a sweetheart. Chelsea has heard this her whole life, that “JACKIE’S A SWEETHEART,” and she bemoans that nobody ever sees how Jacqueline’s irresponsibility is a burden on those who love her.


Chelsea goes to the living room to confront Jacqueline about moving out. But Jacqueline keeps avoiding the subject and keeps asking to play Chelsea her new song. Finally, Chelsea says, “Damn it, Jacqueline, why can’t you ever just talk like a person?” And Jacqueline says, “Because I can’t. What I can do is play you this song.” Chelsea relents and listens to Jacqueline play “THE UKULELE SONG (PART 1)”. In the song, Jacqueline mentions not only that she may have stolen the ukulele, but that the ukulele is all she has as her one comfort in a life she constantly screws up. Well, not her only comfort. She also has her older sister. 


Touched, Chelsea says she can let Jacqueline stay a few more weeks and that she’ll help Jacqueline find a new job. A very happy Jacqueline plays the rest of “THE UKULELE SONG (PART 2)”-- and Chelsea joins in to sing harmony at the very end.


Casting Information

  • CHELSEA - 33 years old, an actuary.

  • JACQUELINE - 30 years old, a singer-songwriter and former barista.

  • WALTER - 35 years old, Chelsea’s well-meaning boyfriend.

  • VOICES - The voices that join in at the end.


Full Show
00:00 / 12:49
Jackie's A Sweetheart
00:00 / 02:21
The Ukulele Song
00:00 / 03:21
The Ukulele Song, Pt. 2
00:00 / 01:07
Casting & Songs



Production History

  • Reading at Muchmore’s in Brooklyn, February 2015.

  • Produced as Episode #13 of the audio podcast TAKE A TEN.

  • Part of Manhattan Musical Theatre Lab’s presentation of TAKE A TEN in New York City on July 23rd, 2015, directed by Emmy-winner Matt Cowart.

  • Finalist, Sound Bites 3.0, a ten-minute musical festival produced by Theatre Now New York. January 18th, 2016, directed by Andrew Lark.

  • Production at Lloydminster Comprehensive High School in Lloydminster, Canada as part of the 2018 Alberta High School Drama Festival, directed by Simon Stang.

  • Production at Memorial Composite High School in Stony Plain, Canada as part of the 2018 Alberta High School Drama Festival, directed by Kevin Tokarsky.

  • Production at Bard Early College High School in Queens, NY as part of their One Act Play Festival in 2018, directed by Whitman Clark.

  • Production directed by John Nichol at Minnesota State University in Mankato, MN, 2018

  • Production directed by Marcia Case at the One Act Festival at the Imperial Theatre in Ontario, CA, 2018

Author Bios

Illustrated Mountains

ANDY RONINSON is a composer, lyricist, orchestrator, and music director living in New York City. He is a recipient of the 2019 Jonathan Larson Grant, a 2019-2020 Dramatists Guild Foundation Fellow, and a participant in the 2017 Johnny Mercer Foundation Songwriters Project. As a member of the BMI Lehman Engel Musical Theatre Writing Workshop, he was awarded the Robert B. Sherman Scholarship and the Harrington Award for Creative Excellence. For more, visit He is the creator, host, and co-writer of TAKE A TEN, the all-original ten-minute musical podcast. Recorded episodes featured Broadway voices like Laura Osnes, Rob McClure, George Salazar, and more. Episodes have been produced live around the world and have won numerous awards including Best Musical twice at Theater Now’s SOUND BITES Festival, the 2016 City Theater National Award for Short Playwriting, and the top place at the Samuel French Off-Off-Broadway Short Play Festival. To hear every episode for free, visit

Illustrated Mountains
Illustrated Mountains
Author's Bios
Production History
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