In an effort to be more transparent, Woolly is now providing a fuller description of the plot and contents.

Content Transparency: This production includes mentions of child abuse, sexual assault, and rape; HIV Stigmatization; Depictions of abusive family situations and homophobia in the family, racist racial fetishization and racist stereotype.

Content Summary:

The play begins with a chorus singing “Usher” repeatedly. Usher is ushering people back to their seat after the intermission of Lion King has concluded, letting the Lion King’s audience in on a little bit of what they are about to witness in that show, while also letting the audience (for A Strange Loop) in on what they will witness in this show. He tells them that, “there will be a young overweigh-to-obese homosexual and/or gay and/or queer, cisgender male, abled-bodied university-and-graduate-school educated, musical theater writing, Disney Ushering, broke-ass middle-class far left-leaning black-identified and classified American descendant of slaves full of self-conscious femme energy and who thinks he’s probably a vers bottom but not totally certain of that obsessing over the latest draft of his self-referential musical A Strange Loop!” The chorus is then introduced as his Thoughts, who then resume singing his name. The chorus of Thoughts play all the roles that aren’t Usher throughout the rest of the musical. They begin singing “Intermission Song.” Usher and his thoughts try to figure out what to write in his musical given all the various expectations put upon him because of his identity.

After the song is over, he decides that his main character, Usher, should have an early dismissal from his shift supervisor, allowing him to go home to work on A Strange Loop. Usher then sings the song “Today,” about how he endeavors to make no compromises today and change his show for the better, even as he deals with difficult tasks in his daily life, like meeting his landlord. The Thoughts visit as various intrusive, bad interruptions. The song ends with him planning to change himself, however he continues to be disturbed by the Thoughts. The workday is done, so Usher sits down to write, but at that moment he gets a call from his mother.

His mother tells him about how there is a rumor going around that Usher touched Nala, his niece, on her vagina, despite how ludicrous it seems to her, but explains that its rumors like that that prevent her from losing weight because she always eats Popeyes after. She then goes on to ask him about what’s going on in his life and if he is still living his purpose. The Thoughts begin, “We Wanna Know,” a song about his mother wanting to know about his life in New York, casting doubt on his dreams. The song ends with all the Thoughts, representing his mother, explicating how they want him to write more like Tyler Perry because he always brings in the Lord, and the thoughts accuse Usher of not loving his Mama or the Lord.

Usher then sings, “Inner White Girl,” poking fun at the many freedoms afforded to white women versus the expectations put on black boys. The song ends with Usher singing about he wants black boys to be able to have all the white girl traits. Usher then faces off against the Guardians of Musical Theater Centrism, who pick apart “Inner White Girl,” and the play overall. They advise him to make the characters fuckable and make the musical about slavery or police violence so that it is “intersectional.”

Then Usher’s dad enters and sings the song, “Didn’t Want Nothing.” His dad is leaving a message to let him know that they were able to dig up Scott Rudin’s number on Google, who his dad heard is a fag as well. He hopes that his son will call him to sell his writing, using their shared queerness as a jumping off point.

The scene then moves to Usher meeting with the doctor. Usher guesses all the doctor’s advice about his health, and his doctor inquires after his sex life. His doctor’s advice to him is to have more sex since he isn’t getting any and prescribes him Truvada just in case. Usher then enters the sexual marketplace, starting the song “Exile in Gayville.” The Thoughts represent various prospective sexual partners who ask if Usher is looking for sex, what he’s into, and if he’s hung. He tries to channel his confident inner white girl, as he chats with various men on the internet. They reject him because he’s black, he’s fat, or his dick is too small, and he confronts them, ending the song by raging at the various ways he’s siloed in the gay community. Usher then sits next to one a man on the train who is reading a smart book. The man looks over his shoulder and asks him what A Strange Loop is. Usher explains that it’s a cognitive science term about how sense of self is a kind of illusion, and the ability to recognize the illusion proves your existence, but it’s also a Liz Phair song. They flirt and Usher learns his name is Joshlet before he reveals that he is the white man of Usher’s dreams. He explains his life story, letting us in on Usher’s ideal man, before offering Usher Popeyes he nutted on and running off with a man named Todrick. Usher writes his exit with an “Indie Rock Underscore.” His thoughts ask him what’s next in the musical, and he sings the song “Second Wave,” about how there is a second-wave feminist in him that is at war with his black gay self. He sings about his difference from many mainstream gay men who are around him.

Usher then gets a call from his agent who is informing him of an exciting opportunity to submit his writing to Tyler Perry, who is looking for a ghostwriter for his gospel plays. Usher and the thoughts sing, “Tyler Perry Writes Real Life.” Usher sings how much he dislikes Tyler Perry’s work, which includes a short reprise of “Today.” The Thoughts become Black Icons: Harriet Tubman, Carter G Woodson, James Baldwin, Zora Neale Hurston, and Whitney, with one person becoming “Twelve Years A Slave.” They sing about how Usher is wrong about Tyler Perry, and praise Tyler Perry’s work. They end the song telling Usher to get off the stage to leave room for Tyler Perry to write real life. Everyone leaves except for Harriet Tubman who tells Usher that at least Tyler Perry is giving people jobs and money. Usher quotes Audre Lorde to her, “But the master’s tools will never dismantle the master’-” before he is cut off by Harriet telling Usher that Lorde is no longer relevant. Usher decides to do the gospel play for the money. He then sings, “Writing a Gospel Play.” He plays out different ideas of what his gospel play might be by improvising all the characters by himself. Usher tells the story of Michelle, who has everything except a husband. Her family tries to teach her how to pray for her husband. Usher eventually runs out of the plot and waves away the Thoughts.

One of them comes up to ask him how many minutes ‘til the end of intermission and starts chatting with him. She figures that this usher job isn’t his dream and asks him what his dream is. Usher explains the musical he is writing to her, and how he has a bit of writer’s block about how the main character should share his artistic dreams with his parents. He fears the implications that writing a confrontation will have on his real life. The patron then tells him to not overcomplicate things, and sings “A Sympathetic Ear.” They advise him to live and write his life truthfully and without fear. Usher, inspired by their song, calls home, and his dad picks up. His dad asks about his personal life and whether he has HIV like his friend Darnell had. Usher tries to get him to stop bringing that up, and their call is interrupted by the rest of his family on his dad’s end of the line. Usher gets the latest news about his family’s drama, with Usher’s family’s names all being character names from The Lion King. Usher is unable to get a word in about his dreams, but his mother asks where her Gospel Play is. Usher hangs up and is invaded by his Thoughts.

Usher then meets a man in Inwood, to have sex. Usher starts to sing, “Inwood Daddy.” Usher laments that though he always means to change his life, he just writes songs, but tonight he is attracted to this Inwood Daddy. Inwood Daddy offers Usher poppers which he refuses, and Usher insists that he wear a condom. Usher then contemplates whether he should have sex with this white man who fetishizes him. They have sex as Inwood Daddy says slurs to Usher, and Usher moans and the Thoughts underscore the scene singing short phrases like “White Only” and “Jim Crow.” After Inwood Daddy comes, Usher gets up to leave and go do his work. Inwood Daddy tries to convince him to stay by offering homemade grits or leftover Popeyes.
Usher leaves and sings “Boundaries,” where he questions his actions and how he has no boundaries. The song ends and as

Usher does his walk of shame from Inwood, which takes him deeper into a strange loop, he gets his annual birthday voicemail from his mom, represented in the song “Periodically.” His mom sings, detailing her love for him and encouraging him, marveling about how he turned 26 on the 26th. She then continues to tell him about how homosexuality is wrong according to the bible and how he’ll go to hell for being gay. After Usher finishes listening to the voicemail, his daily self-loathing Thought arrives and Usher fights them for a moment before he receives a call from his father, in the form of the song “Didn’t Want Nothin’ (reprise).” Usher listens as his mother and father fight about his descent into sin because he’s gay, and their fear of God punishing him with AIDs like what happened to his friend Darnell. Usher explains that though he’s gay that doesn’t mean he’s constantly having sex, in fact he has sex rather rarely, and he explains the various societal factors that make it that way. His father asks him what he actually wants from him to which Usher says that he wants him to like his work and this show, that he wants him to care about his complexity. His father says he doesn’t like this show or care about his complexity. His mother and father start shouting at each other, and his father leaves. His mother asks him why he hates them because it seems like he hates them from the way they’re written into the show. Usher declares that he writes them like that because he loves them.

They then start the song, “Precious Little Dream/AIDS is God’s Punishment.” Usher’s mother tells him how disappointed she is in his lifestyle and choices, and Usher sings about all the way she’s hurt him. The song transforms into a Gospel Play with Usher transforming into The Color Purple version, then the Real Housewives version, and finally the megachurch pastor version of himself. In this final version, he monologues and sings about how AIDS is punishment for homosexuals like him and Darnell who stray from God’s light. The Thoughts join him as church choir. The choir continues to sing as Usher talks about visiting Darnell in the hospital, how he refused HIV medication because he knew the wages of sin was death. When the monologue concludes, the choir returns to singing with Usher leading them, but his mother calls for them to stop. She takes Usher in her arms and tells him he is loved and how talented he is. His play has helped her realize how much he was struggling, and she feels bad for poor Darnell. However, she still attributes his suffering to his choice in lifestyle, saying that they’re going to get Usher on the right track. His mother gets called away in the scene.

The Thought playing her asks him if this is really how he wants A Strange Loop to end, with these hateful Tyler Perry Cartoon versions of his parents. He says that they weren’t cartoons and that they were complex, and that he was trying to depict life as it was for him when he was 17. The Thought reminds him that he is 26. Usher begins to think about what to do next, realizing that for his perceptions of his parents to change he must change as well. He sings, “Memory Song,” singing about what it was like to be a young, lone, Black gay boy turning away from the Lord. He ends the song by singing about the Black gay boys who chose to go back to the Lord. He muses on whether that’s how the show ends, with him turning his back like he did to the Lord, or if it should all start over and nothing changes, or if the audience can’t go home until he faces himself. The Thoughts all echo him, saying, “Facing himself,” and then Usher sings “A Strange Loop (Finale),” facing a looping funhouse corridor of himself. He sings about how he feels about himself in relationship to others, noting his difference and how that causes him agony. He ends saying that “Change is Just an Illusion” and the Thoughts all echo “Just an Illusion” building up to a stirring final moment of wondering at the Strange Loop.