[1] First produced off-Broadway in 2019, then staged in Washington, D.C. in 2021,[2] A Strange Loop premiered on Broadway at the Lyceum Theatre in April 2022.

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").

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'").

Usher starts using dating apps but is rejected, causing him to rage against the gay community ("Exile In Gayville").

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").

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 homosexuality is a sin ("Periodically") while his father calls to inform him their church community does not approve of his music ("Didn't Want Nothin' [Reprise]").

[10] 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.

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.

[19] Kyle Ramar Freeman, who understudied Usher on Broadway, starred in the production alongside an all-British cast of Thoughts.

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.

[33] 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."

As one of its producers, Jennifer Hudson became the second Black woman to receive all four of the major American entertainment awards (EGOT).