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A Strange Loop is a 2020 musical play by Michael R. Jackson.

The protagonist is Usher, a gay black man who works as, wait for it, an usher for the Broadway production of The Lion King. (In theory at least, the entire play takes place during an intermission of The Lion King). Usher is writing a play called A Strange Loop, which is about...a gay black man named Usher, who works as an usher for The Lion King, and is writing a play called A Strange Loop, which is about a gay black man named Usher...

The play is about Usher's struggle to make it in musical theater and finish writing his show. He also has to deal with the problems of being a black man working in a white world (musical theater), a gay black man who can't stop himself from having degrading fetish sex with white men, and, most problematic, a gay black man with a very traditional family that includes parents that love Tyler Perry and strongly disapprove of their son's homosexuality. The cast consists of Usher and six "Thoughts", who play many characters, including his parents, his agent, the white guy who invites Usher home for some demeaning sex, and a character referred to in the stage directions as "Usher's self-loathing."

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Tropes:

  • All Gays Love Theater: And they write shows, too!
  • Author Avatar: Usher is basically a fictionalized version of Michael R. Jackson, a gay black man with two advanced arts degrees who works in musical theater.
  • Country Matters: Usher's mom (played by Thought 2) complains about how Usher's brother's baby mama spray painted "See You Next Tuesday" on Mom's car. When clueless Dad says "See you next Tuesday?!", Mom explains "Cunt!".
  • Droste Image: The poster and cover for the script shows a black man whose body consists of theater curtains looking down, parting the curtains, and revealing inside the exact same image, of himself, parting the curtains and revealing the image again and again to infinity.
  • Greek Chorus: Thoughts 1-6, who comment on the action, mercilessly mock Usher, and play a variety of characters, like Usher's family or his agent.
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  • Have You Tried Not Being a Monster?: Usher's parents are still hopeful that his homosexuality is a phase and that eventually he'll marry a woman and give them grandchildren.
  • Medium Awareness: Usher and the Thoughts are aware that they are in a play called A Strange Loop. Near the end, Thought 4 urges Usher to make a decision about his life and wrap things up, because the white people in the audience want to go home.
  • Money, Dear Boy: In-Universe. His agent pushes Usher to ghost-write a Tyler Perry "gospel play," but Usher hates Tyler Perry and all his works. Finally Usher caves and says he'll do it, "but only for the money."
  • Most Writers Are Writers: Usher is a writer who is struggling to write his play. Lampshaded in the opening number where Thoughts 5 and 6 sing that "NO ONE CARES ABOUT A WRITER/WHO IS STRUGGLING TO WRITE."
  • The Musical: An aspiring playwright, attempting to write a musical, with a chorus of his own thoughts telling him how much he sucks.
  • N-Word Privileges: Thought 2, criticizing Usher's story, says "You can't say 'N' in a musical," because "white people are watching."
  • Reading Ahead in the Script: At one point the Thoughts, who are very skeptical of Usher's writing choices, are thumbing through the script of A Strange Loop. Thought 3 gets to the end, where Usher turns his back to the audience, and says "That's seriously how the show ends?"
    Usher: Possibly. In this draft at least.
    Thought 3: Hmm. Well, that's certainly a choice.
  • Recursive Reality: The show consists of Usher trying to figure out how to write his play, A Strange Loop, while his thoughts comment on the action.
  • Shout-Out: Usher talks how much he likes Liz Phair and how the name of the play is partially inspired by her song "Strange Loop". He says Phair wouldn't grant permission to use her music but "her spirit lives on in the piece in other ways." A whole scene is called "Exile in Gayville", from Phair's iconic album Exile in Guyville.
  • Subverted Rhyme Every Occasion: The Thoughts sing that white theater critics aren't going to like his show. They sing "WATCH THEM WRITE YOU OFF AS LAZY/NOT TO MENTION NAVEL-GAZEY/LACKING BOTH IN CRAFT AND RIGOR/'CAUSE YOU'RE JUST A FUCKING NIG—", and then the song goes back to the chorus with "BIG, BLACK, AND QUEER-ASS AMERICAN BROADWAY SHOW."
  • Take That!: A quite long section of the show is dedicated to how much Tyler Perry sucks. His agent strongarms him into ghost writing a Tyler Perry show. Usher's family then sings a whole song about how Tyler Perry is the best and writes about "real life". This is followed by a Show Within a Show scene from Usher's Tyler Perry play, which is deeply stupid.
  • Title Drop: The name of the show is mentioned several times. In one scene Usher explains the title to Thought 5, saying that it comes from the book by Douglas Hofstadter where Hofstadter describes the sense of self or "I" as an illusion produced by repeated stimuli in the brain, and calls it "a strange loop."
  • Write What You Know: In-Universe and in fact spoken word for word, as Thoughts 4-6, representing Usher trying to figure out what the story should be, sing "SOME SAY WRITE FROM EXPLORATION/SOME SAY JUST WRITE WHAT YOU KNOW."
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