A Strange Loop

The chorus, Usher's Thoughts, calls Usher's name many times. Usher, working as an usher for The Lion King, tells the audience what the show will entail. Usher wonders how he should write A Strange Loop to represent what it's like to "travel the world in a fat, Black, queer body" ("Intermission Song").

After work, Usher plans "to change this show for the better". Usher wants to change himself, but his Thoughts, full of self-loathing and worry, are too disruptive ("Today"). His mother calls to ask "what's going on in [his] life" and reminds him how hard she and his father worked to raise him. She requests that Usher write a Tyler Perry-style gospel play in return ("We Wanna Know").

Usher wishes he could act more like his "inner white girl" but is held back by expectations put on Black boys ("Inner White Girl"). Usher's Thoughts criticize "Inner White Girl" and the show, claiming the main character should have more sex appeal and telling him to add elements of "slavery or police violence so that the allies in the audience have something 'intersectional' to hold onto".

Usher’s father leaves a voicemail saying that he found Scott Rudin’s number online. Because Usher has student loans to pay off, his father urges him to leverage their common sexuality to make a connection, despite not condoning homosexuality ("Didn't Want Nothin'").

At a medical checkup, Usher's doctor inquires about Usher's sex life and prescribes him Truvada, pressuring Usher to have more sex. Usher "enters the sexual marketplace" through various gay dating apps but is rejected for being "too Black, too fat, too feminine," and for having a small dick. Usher rages against the ways in which the gay community is also discriminatory ("Exile In Gayville").

A stranger on a train asks what Usher is writing. Usher explains that "A Strange Loop" is a cognitive science term about how "your ability to conceive of yourself as an 'I' is ... an illusion. But the fact that you can recognize the illusion proves it exists." The stranger introduces himself as Joshlet, and the two flirt before Joshlet reveals that he's a figment of Usher's imagination. Joshlet dismisses Usher, who sings about how "the second-wave feminist in [him] is at war with the dick-sucking Black gay man" ("Second Wave").

Usher's agent informs him that Tyler Perry is seeking a ghostwriter for a gospel play, but Usher has a low opinion of Perry’s work. Appearing as famous Black figures such as Harriet Tubman, Carter G Woodson, James Baldwin, Zora Neale Hurston, and Whitney Houston, his Thoughts accuse him of being a race traitor and persuade him to take the job "for the money. And Mom. And Dad. And the ancestors" ("Tyler Perry Writes Real Life"). Usher writes the play, acting out all the characters as caricatures ("Writing a Gospel Play").

Back at work, Usher tells a patron he can't continue the show without confronting his parents with his artistic self. The patron advises him to live his life without fear ("A Sympathetic Ear"). Usher's father calls to ask if he has HIV like his cousin Darnell had. The rest of his family appears, and the call quickly devolves. His mother asks where her gospel play is.

Usher hooks up with a white man, Inwood Daddy, who fetishizes him and calls him racial slurs ("Inwood Daddy"). After Usher leaves, he questions where his boundaries are ("Boundaries").

His mother leaves a voicemail wishing him a happy birthday, also telling him homosexuality is a sin ("Periodically"). His father calls to tell him their church community doesn't approve of his music ("Didn’t Want Nothin' (reprise)"). Usher's parents argue with him over his homosexuality and worry he might catch AIDS before Usher explodes about how his upbringing, repressed sexuality, and lack of support from his father hurt him. Usher and his mother fight about her portrayal in the play, and she accuses Usher of hating and disappointing her.

The set transforms into a gospel play with Usher as a church pastor and the Thoughts as a choir. Usher recalls how Darnell, thinking he deserved to die for his sins, refused HIV medication in the hospital. Usher realizes "the only thing worse than dying of AIDS would be living with it and hearing the people you loved say 'I told you so.'" Usher's mother stops the show ("Precious Little Dream/AIDS Is God's Punishment"). She tells Usher he is loved but thinks he's struggling because homosexuality is a sin, wishing they could "work this gay abomination thang out".

The Thought playing his mother asks if he wants to end the show with hateful caricatures of his parents. Usher says he was trying to depict life as it was when he was seventeen, but the Thought reminds him that he is now twenty-six. Usher realizes that for his perceptions of his parents to change, he must change as well. He sings about what it was like to be "one lone, Black gay boy ...who chose to turn his back on the Lord" ("Memory Song"). With his back to the audience, Usher wonders what will happen when the show ends. He turns, reflecting on himself, his relationship with others, and what would happen if he were to change, and comes to the conclusion that "change is just an illusion" and that they are in a strange loop.

• "Intermission Song" – Usher, Thoughts
• "Today" – Usher, Thoughts
• "We Wanna Know" – Thoughts
• "Inner White Girl" – Usher, Thoughts
• "Didn't Want Nothin'" – Thought 5, Thoughts
• "Exile in Gayville" – Usher, Thoughts
• "Second Wave" – Usher
• "Tyler Perry Writes Real Life" – Usher, Thought 3, Thoughts
• "Writing a Gospel Play" – Usher, Thoughts
• "A Sympathetic Ear" – Thought 1
• "Inwood Daddy" – Usher, Thought 6, Thoughts
• "Boundaries" – Usher
• "Periodically" – Thought 4, Usher
• "Didn't Want Nothin' Reprise" – Thought 5
• "Precious Little Dream / AIDS Is God's Punishment" – Usher, Thoughts
• "Memory Song" – Usher, Thoughts 2-6
• "A Strange Loop" – Usher, Thoughts

Upon opening off-Broadway on 17 June 2019. A Strange Loop received good critical acclaim. In particular, it was praised for its emotional honesty and meta themes within both the writing and the musical compositions. It was also praised for the performances that the cast gave, calling them “physically exhaustive.” However, it was deemed as unlikely to become a Broadway show due to it potentially getting "too easily lost in a Broadway House."[20]

A Strange Loop opened on Broadway on 26 April 2022 and also received good critical acclaim. In particular, it was praised for its themes and tone which were successfully retained from the off-Broadway version and then cleaned up for the larger, more consumer based crowd which would be found on Broadway. There was a light critiquing about how working within the large institution of Broadway instead of merely peering in has made some of the commentary become shallow.[21][22]

The original off-Broadway cast recording was released on September 27, 2019, on Yellow Sound Label.[23] The album peaked at number 6 on the Billboard Cast Albums chart.[24] A Broadway cast album was recorded on April 10, 2022 and released on June 10, 2022 through Sh-K-Boom Records, Yellow Sound Label, Barbara Whitman Productions, and Ghostlight Records.[25] It debuted at number two on the Cast Albums chart.[26] The cast recording received a Grammy nomination for Best Musical Theater Album for the 65th Annual Grammy Awards, to be held in February 2023.

On June 14, 2022, Deadline reported that the musical filled 98% of its available seats during the week ending June 12. The musical grossed $676,316 for seven performances.[27] The musical also broke the Lyceum Theatre box office house record for a standard 8-performance week, taking $860,496 for the week ending June 26, a $15,183 bump over the previous week.[28] As of September 2022, A Strange Loop grossed around $14.2 million from 136,777 attendance and 157 performance.[29]

On May 4, 2020, the Pulitzer Prize for Drama was awarded to Jackson for the musical, with the committee citing the show as "a metafictional musical that tracks the creative process of an artist transforming issues of identity, race, and sexuality that once pushed him to the margins of the cultural mainstream into a meditation on universal human fears and insecurities." The show is the tenth musical to win the award, as well as the first musical written by a Black person to win and first musical to win without a Broadway run.[30] The show premiered on Broadway in April 2022 and won the Tony Award for Best Musical. As one of its producers, Jennifer Hudson became the second Black woman to receive all four of the major American entertainment awards (EGOT).[31]

The cast recording received a nomination for the Grammy Award for Best Musical Theater Album for the 2023 Grammy Awards, which it lost to the 2022 Broadway cast recording of Into the Woods.