A Strange Loop

While working as an usher at The Lion King, aspiring musical theater writer Usher contemplates the show he is writing, wanting it to represent what it is like to "travel the world in a fat, black, queer body" ("Intermission Song"). He plans to change himself, but his thoughts are too disruptive ("Today"). His mother, who constantly reminds him how hard she and his father worked to raise him, calls with a request that he write a Tyler Perry-style gospel play ("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"). His Thoughts criticize the show, claiming the main character should have more sex appeal and telling him to add certain elements. Usher's father leaves a voicemail saying he found Scott Rudin's number and urges him to leverage their common sexuality to make a connection ("Didn't Want Nothin'").

At a medical checkup, Usher's doctor inquires about his sex life and prescribes Truvada. Usher starts using dating apps but is rejected, causing him to rage against the gay community ("Exile In Gayville"). A stranger flirts with Usher before revealing he is a figment of Usher's imagination and dismissing the war between the "second-wave feminist" and "the dick-sucking Black gay man" within him ("Second Wave").

Usher's agent tells him 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, his Thoughts accuse him of being a race traitor and persuade him to take the job ("Tyler Perry Writes Real Life"). Usher writes the play, acting out all the characters as caricatures ("Writing a Gospel Play").

At work, Usher tells a patron he cannot continue the show without confronting his parents with his artistic self. The patron advises him to live without fear ("A Sympathetic Ear"). Usher speaks with his parents over the phone, his father asking if he has contracted HIV and his mother asking about the status of the gospel play. After hooking up with "Inwood Daddy", a white man who fetishizes him and calls him racial slurs, Usher questions his "Boundaries".

On his birthday, Usher's mother leaves a voicemail reminding him that homosexuality is a sin ("Periodically") while his father calls to inform him their church does not approve of his music ("Didn't Want Nothin' [Reprise]"). While arguing with his parents, Usher's mother, horrified by her portrayal in the play, accuses him of hating and disappointing her. Usher recalls how his friend Darnell, thinking he deserved to die, refused HIV medication and concludes living with AIDS is worse than dying from it ("Precious Little Dream/AIDS Is God's Punishment"). His mother tells Usher he is loved but thinks he is struggling because of his homosexuality.

The Thought who is portraying Usher's mother breaks the fourth wall, asking Usher if he wants the show to end with hateful caricatures of his parents. Usher claims that he is depicting life as it was when he was 17, to which the Thoughts remind him he is now 26. Usher then reflects on his childhood, realizing his perceptions must change before he can change ("Memory Song"). With his back to the audience, Usher wonders what will happen when the show ends. He turns around, concluding that he does not need to change because change is an illusion, and he, like everyone else, is 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

A Strange Loop began previews at off-Broadway venue Playwrights Horizons on May 24, 2019. It opened on June 17, 2019, with closing scheduled for July 7, 2019,{{Cite web |title=A Look at A Strange Loop Off-Broadway |url=https://playbill.com/article/a-look-at-a-strange-loop-off-broadway |access-date=April 19, 2022 |website=Playbill |language=en}} before extending to July 28, 2019.{{Cite web |title=Michael R. Jackson's A Strange Loop Extends Off-Broadway |url=https://playbill.com/article/michael-r-jacksons-a-strange-loop-extends-off-broadway |access-date=April 19, 2022 |website=Playbill |language=en}} The show featured Larry Owens as Usher. The creative team credits included Michael R. Jackson as writer of book, music, and lyrics, Stephen Brackett as director, Raja Feather Kelly as choreographer, Charlie Rosen as orchestrator, and Rona Siddiqui as music director.{{Cite web |title=See the Cast and Creative Team of A Strange Loop Meet the Press |url=https://playbill.com/article/see-the-cast-and-creative-team-of-a-strange-loop-meet-the-press |access-date=April 19, 2022 |website=Playbill |language=en}}

The Washington, DC production at Woolly Mammoth Theatre Company was originally scheduled for September 2020, but postponed to December 2021 due to the COVID-19 pandemic.{{Cite web|last=Culwell-Block|first=Logan|date=May 15, 2020|title=Broadway-Aimed D.C. Production of A Strange Loop Postponed to Summer 2021|url=http://www.playbill.com/article/broadway-aimed-dc-production-of-a-strange-loop-postponed-to-summer-2021|access-date=September 15, 2020|website=Playbill|language=en}}{{Cite web |last=Gans |first=Andrew |date=December 3, 2021 |title=Michael R. Jackson's A Strange Loop Opens at Woolly Mammoth December 3 |url=https://www.playbill.com/article/michael-r-jacksons-a-strange-loop-opens-at-woolly-mammoth-december-3 |access-date=December 20, 2021 |website=Playbill}} The six-week limited run began previews November 22, 2021, and opened December 3, 2021.{{Cite web |title=Take a 1st Look at Michael R. Jackson's A Strange Loop at the Woolly Mammoth Theatre |url=https://playbill.com/article/take-a-1st-look-at-michael-r-jacksons-a-strange-loop-at-the-woolly-mammoth-theatre |access-date=April 19, 2022 |website=Playbill |language=en}} The show extended another week, changing its closing date from January 2 to 9, 2022.{{Cite web |title=Odds & Ends: Michael R. Jackson's A Strange Loop Extends Run in Washington, D.C. |url=https://www.broadway.com/buzz/201663/odds-ends-michael-r-jacksons-a-strange-loop-extends-run-in-washington-dc/ |access-date=April 19, 2022 |website=Broadway.com |language=en}}

The Broadway production of A Strange Loop was announced December 20, 2021.{{Cite web |title=Pulitzer-Winning A Strange Loop to Play Broadway |url=https://playbill.com/article/pulitzer-winning-a-strange-loop-to-play-broadway |access-date=April 19, 2022 |website=Playbill |language=en}} Many notable people from the entertainment industry served as the show's producers. They included lead producer Barbara Whitman, as well as Benj Pasek, Justin Paul, Jennifer Hudson, RuPaul Charles, Marc Platt, Megan Ellison of Annapurna Pictures, Don Cheadle, Frank Marshall, James L. Nederlander, Alan Cumming, Ilana Glazer, Mindy Kaling and Billy Porter.{{Cite web|url=https://www.theatermania.com/broadway/news/rupaul-alan-cumming-billy-porter-a-strange-loop_93648.html|title=RuPaul, Alan Cumming, and Billy Porter Among the Many Producers of A Strange Loop|website=Theatermania.com|date=April 13, 2022 |access-date=May 25, 2022}} Previews were scheduled to begin on April 6, but were postponed to April 14 due to COVID-19 breakouts among the cast.{{Cite web |title=Update: A Strange Loop Broadway Start Postponed to April 14 |url=https://playbill.com/article/update-a-strange-loop-broadway-start-postponed-to-april-14 |access-date=April 19, 2022 |website=Playbill |language=en}} The show officially opened April 26, 2022. In October 2022, it was announced that the show would play its final performance on Broadway on January 15, 2023.{{cite web |last1=Culwell-Block |first1=Logan |title=Broadway's A Strange Loop Will Close in January |url=https://www.playbill.com/article/broadways-a-strange-loop-will-close-in-january |website=playbill.com |access-date=October 23, 2022 |archive-url=https://web.archive.org/web/20221013034327/https://www.playbill.com/article/broadways-a-strange-loop-will-close-in-january |archive-date=October 13, 2022 |date=October 11, 2022 |url-status=live}}

The London production opened at the Barbican Centre on June 17, 2023, for a limited run until September 9. It was produced by Howard Panter for Trafalgar Theatre Productions, the National Theatre, Barbara Whitman and Wessex Grove.{{cite web |first=Alex| last=Wood| title=A Strange Loop to have UK premiere this summer | website=WhatsOnStage | date=March 8, 2023 | url=https://www.whatsonstage.com/london-theatre/news/a-strange-loop-barbican-musical_58494.html | access-date=March 21, 2023}} Brackett, Kelly, Rosen, Siddiqui, and the rest of the Broadway creative team returned for the London production.{{Cite web |last=Culwell-Block |first=Logan |date=April 28, 2023 |title=Kyle Ramar Freeman to Lead A Strange Loop in London's West End |url=https://www.playbill.com/article/kyle-ramar-freeman-to-lead-a-strange-loop-in-londons-west-end |access-date=April 28, 2023 |website=Playbill}} Kyle Ramar Freeman, who understudied Usher on Broadway, starred in the production alongside an all-British cast of Thoughts.{{cite web |last1=Cullwell-Block |first1=Logan |title=A Strange Loop Begins London Premiere Starring Broadway's Kyle Ramar Freeman June 17 |url=https://playbill.com/article/a-strange-loop-begins-london-premiere-starring-broadways-kyle-ramar-freeman-june-17 |website=Playbill |access-date=June 22, 2023}} Freeman played his final performance on August 12 due to prior commitments. Kyle Birch stepped into the role of Usher on August 14 and continued through the show's final performance.{{Cite web |last=Wild |first=Stephi |title=Kyle Birch Will Lead A STRANGE LOOP in London as 'Usher' |url=https://www.broadwayworld.com/westend/article/Kyle-Birch-Will-Lead-A-STRANGE-LOOP-in-London-as-Usher-20230814 |access-date=2023-08-15 |website=BroadwayWorld.com |language=en}}

A Strange Loop played as a co-production between American Conservatory Theater (A.C.T.) in San Francisco and the Center Theatre Group in Los Angeles, presented at A.C.T. from April 18 to May 12, 2024, and the Center Theatre Group's Ahmanson Theatre from June 5 to June 30, 2024. The production was helmed by the same creative team as the Broadway and London mountings and featured a largely new cast as Usher and the Thoughts, with John-Andrew Morrison reprising his role as Thought 4.{{cite web |last1=Rabinowitz |first1=Chloe |title=John-Andrew Morrison, Malachi McCaskill & More to Star in A STRANGE LOOP West Coast Premiere |url=https://www.broadwayworld.com/article/John-Andrew-Morrison-Malachi-McCaskill-More-to-Star-in-A-STRANGE-LOOP-West-Coast-Premiere-20240306 |website=BroadwayWorld |access-date=6 March 2024}}{{cite web |last1=D'Souza |first1=Karen |title=Review: 'A Strange Loop' is a lively, engrossing head trip in West Coast premiere |url=https://www.marinij.com/2024/04/26/review-a-strange-loop-is-a-lively-engrossing-head-trip-in-west-coast-premiere/ |website=Marin Independent Journal |date=April 26, 2024 |access-date=15 September 2024}}

Upon opening off-Broadway on June 17, 2019. A Strange Loop received 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."{{cite journal |last1=Savran |first1=David |title=A Strange Loop by Michael R. Jackson (review) |journal=Johns Hopkins University Press |date=June 2020 |volume=72 |issue=2 |page=219-221 |url=https://muse.jhu.edu/pub/1/article/759546/pdf |access-date=April 29, 2023}}

A Strange Loop opened on Broadway on April 26, 2022, and also received 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.{{cite web |last1=Shaw |first1=Helen |title=A Strange Loop Moves to Broadway, Its Furious Energy Changed but Intact |url=https://www.vulture.com/2022/04/theater-review-a-strange-loop-broadway.html |website=Vulture |date=April 26, 2022 |access-date=April 29, 2023}}{{cite web |last1=Francia |first1=Caryl Anne |title='A Strange Loop' tells comedic, honest story of embracing oneself |url=https://theticker.org/7724/arts/a-strange-loop-tells-comedic-honest-story-of-embracing-oneself/ |website=The Ticker |date=May 13, 2022 |access-date=April 29, 2023}}

The original off-Broadway cast recording was released on September 27, 2019, on Yellow Sound Label.{{cite web|url=https://www.amazon.com/Strange-Loop-Original-Cast-Recording/dp/B07VXZPNCH|title=A Strange Loop (Original Cast Recording)|website=Amazon Music|access-date=April 26, 2020}} The album peaked at number 6 on the Billboard Cast Albums chart.{{cite magazine|url=https://www.billboard.com/charts/search?artistname=&charttitle=a+strange+loop&label=&chartcode=&chart_date=|title=Chart Search|magazine=Billboard|access-date=May 28, 2020}} 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.{{cite web|url=https://playbill.com/article/pulitzer-winning-a-strange-loop-to-record-broadway-cast-album|title=Pulitzer-Winning A Strange Loop to Record Broadway Cast Album|last=Culwell-Block|first=Logan|work=Playbill|date=March 31, 2022|access-date=April 18, 2022}} It debuted at number two on the Cast Albums chart.{{cite magazine|url=https://www.billboard.com/charts/cast-albums/2022-06-25/|title=Cast Albums – June 25, 2022|magazine=Billboard|access-date=June 21, 2022}}

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.{{cite web|url=https://deadline.com/2022/06/broadway-box-office-strange-loop-plaza-suite-music-man-1235045170/|title=Pre-Tony Broadway Box Office Up 7% To $32M; 'Strange Loop' Fills 98% Of Seats|website=Deadline|date=June 14, 2022}} 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.{{cite web|url=https://deadline.com/2022/06/broadway-box-office-june-26-strange-loop-house-record-1235053374/|title=Broadway Box Office Holds Steady At $31M; 'A Strange Loop', 'MJ' Set House Records|website=Deadline|date=June 28, 2022}} As of September 2022, A Strange Loop grossed around $14.2 million from 136,777 attendance and 157 performances.{{cite web|url=https://www.broadwayworld.com/grosses/A-STRANGE-LOOP|title=A STRANGE LOOP|website=Broadway World|date=September 20, 2022}}

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.{{cite web|url= https://www.pulitzer.org/winners/michael-r-jackson|title=A Strange Loop, by Michael R. Jackson|website=The Pulitzer Prizes|access-date=May 4, 2020}} 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).{{Cite web |date=June 13, 2022 |title=With the Tony-winning 'A Strange Loop,' Jennifer Hudson becomes an EGOT recipient |url=https://www.latimes.com/entertainment-arts/story/2022-06-12/jennifer-hudson-egot-winner |access-date=June 13, 2022 |website=Los Angeles Times |language=en-US}}

The cast recording received a nomination for the Grammy Award for Best Musical Theater Album for the 2023 Grammy Awards.

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