"A Strange Loop" - by Michael R. Jackson - SpeakEasy Stage Company (Boston, MA.) - REVIEW

(Cover Photo: Kai Clifton as "Usher" and the CAST of Michael R. Jackson's "A STRANGE LOOP" produced jointly by Front Porch Arts Collective and SpeakEasy Stage Company in Boston, MA. until May 25, 2024. Photo credit Maggie Hall Photography)

By Kevin T. Baldwin

METRMAG Reviewer

# 774-242-6724 

“These are my memories. Sweet sour memories. This is my history. This is my mystery.” 

                                - ("Usher") / Michael R. Jackson

SpeakEasy Stage Company

in Association with 

Front Porch Arts Collective 

Presents Michael R. Jackson's 

Tony Award-winning Musical 


Winner! 2020 Pulitzer Prize for Drama and 2022 Tony Award for Best Musical 

A Co-Production with Front Porch Arts Collective

Book, Music & Lyrics by Michael R. Jackson

Directed by Maurice Emmanuel Parent

Cast Includes: Kai Clifton as “Usher,” Grant Evan as “Thought # 1,” De’Lon Grant as “Thought # 5,” Jonathan Melo as “Thought # 3,” Zion Middleton as “Thought # 6,” Davron S. Monroe as “Thought # 2,” Aaron Michael Ray as “Thought # 4”

Additional Creative Team: 

Asst. Stage Manager - Ashley Pitchford; Costumer Designer - Becca Jewett; Props Designer - Emme Shaw; Wardrobe Supervisor - Becca Cottrell; Asst. Director - Jalen Bunch; Scenic Designer - Jon Savage**; Asst. Cost. Designer - Harlan White; Production Engineer - Irene Wang; Intimacy Director - Greg Geffard; Prod. Stage Manager - Elizabeth Yvette Ramirez*; Lighting Designer - Brian J. Lilienthal**; Sound Designer - David Remedios**; Mix Engineer - Lexie Lankiewicz; Asst. Intimacy Director - Phoebe Gonzales    

* Member of Actors’ Equity Association, the Union of Professional Actors and Stage Managers in the United States 

** Represented by United Scenic Artists, Local USA 829 of the IATSE 


April 26, 2024 through May 25, 2024 

(Contact Box Office for Exact Times)  

Calderwood / BCA, 527 Tremont Street, Boston MA 02116 


Contact the Box Office # 617-933-8600 or visit  www.speakeasystage.com 



Contact Venue for Most Updated COVID-19 Safety Protocols and Information.

SpeakEasy Stage Company concludes a fabulous 33rd season with Michael R. Jackson’s profound musical, "A STRANGE LOOP," in collaboration with Front Porch Arts Collective.

Walking into the May 1st performance, I had no real idea what to expect. 

I thought I did, but...I didn't.

Oh, I knew of the "basic" premise and had performed all my normal due diligence of research before seeing it. 

So, in advance, I knew "basically" what this musical was about and what to expect. Right?


As the lights came up and the story began, I soon realized that my expectations of anything "basic" had just been flung out the window and I had absolutely no clue what I was in for over the next hour and 40 minutes (no intermission).

There are going to be many reviews full of praise for many aspects of this show...and, yes, this is going to be one of them.

However, the main aspect I did not expect I would be praising comes in the form of the courage - the tremendous courage - it must have taken for author Michael R. Jackson to have so completely and vulnerably bared his soul as he has done here. 

(Note: According to the show's program, Johnson's pronouns used are indicated as "He/Him" while Kai Clifton, the actor playing the character "Usher," uses the pronoun's "He/They.")

(Photo: Kai Clifton as "Usher" is surrounded by "Thoughts" (clockwise from lower left: Grant EvanAaron Michael RayDe'Lon GrantZion MiddletonDavron S. Monroe, and Jonathan Melo) in a moment from Michael R. Jackson's "A STRANGE LOOP" now playing at SpeakEasy Stage Company in Boston, MA. until May 25, 2024. Photo credit Maggie Hall Photography)

The title is an homage to the cognitive science term coined by Douglas Hofstadter, as well as a song by Liz Phair

In his 2007 book, “I Am a Strange Loop, Hofstadter states: “In the end, we are self-perceiving, self-inventing, locked-in mirages that are little miracles of self-reference.” (This concept was first explored in his 1979 book, “Gödel, Escher, Bach.”

In "A STRANGE LOOP," we meet Usher (Kai Clifton), a "plus-size" Black queer man, writing a musical about a "plus-size" Black queer man writing a musical. 

Usher is seemingly used as a "vessel" through which Jackson can tell his own remarkable story.

While the musical’s message appears to speak to specific groups, this musical ultimately found a more widespread audience. 

"A STRANGE LOOP" was first produced Off-Broadway in 2019, then staged in Washington, D.C. in 2021, ultimately hitting Broadway in 2022

It would continue on Broadway until January, 2023

With book, music, and lyrics by Jackson, "A STRANGE LOOP" would go on to win Best Musical and Best Book of a Musical at the 75th Tony Awards

It also won the 2020 Pulitzer Prize for Drama, making Jackson the first openly gay Black man upon which this honor has been bestowed. 

All the warranted praise and accolades aside, this is still a musical that is not going to appeal to every individual's taste and it doesn't appear that was ever the intent by Jackson, either.

However, while your own experience may vary, even if there aren't tunes you might walk away from the theatre humming with a spring in your step, thanks to a clear, concise vision by director Maurice Emmanuel Parent, the musical itself, executed by an astounding "dream cast," is overwhelming in its beauty.

This beauty comes out of its complexity - this is a story that is simultaneously whimsical and sad, optimistic and pessimistic, ethereal and as real as it gets.

"A STRANGE LOOP" addresses outward societal shortsightedness but does so in an inventive fashion. 

Yet, Jackson also pulls no punches in addressing internal conflicts of shortsightedness as "LOOP" looks at its own community.

From Usher’s opener, the hilarious “Intermission Song” straight through to the show’s sympathetic “Memory Song” which moves into the show’s closing title number, “A Strange Loop, the respective emotional connotations are apparent in each and every well-crafted lyric. 

(Photo: Kai Clifton as "Usher" and the CAST of Michael R. Jackson's "A STRANGE LOOP" produced jointly by Front Porch Arts Collective and SpeakEasy Stage Company in Boston, MA. until May 25, 2024. Photo credit Maggie Hall Photography)

Usher, in a literary sense, augments their own "LOOP," working as an usher at Broadway’s “The Lion King.” 

In a “Circle of Life” kind of way, it appears Usher is completely obsessed in creating a show about a "plus-size" Black gay man who is writing…(okay, you get the idea)…so much so that Usher becomes an annoyance to those around them. 

Compounding their professional turmoil, Usher also must contend with their own personal demons in New York City’s “queer scene” as a large, heavyset Black man. 

Usher tries online dating but is repeatedly rejected, resulting in a verbal assault on (and by) the gay community in the highly charged and emotional musical number, "Exile In Gayville.” 

During a doctor’s appointment, Usher's doctor asks about, then berates, Usher’s sex life and prescribes a medication at which Usher condemns. 

Usher is lonely. 

So lonely, in fact, that self-loathing has placed its relentless grip upon the throat of this usher named "Usher."

Even Usher’s own family members appear to be part of Usher’s endless "LOOP" of “Thoughts” (Grant Evan as “Thought # 1,” Davron S. Monroe as “Thought # 2,” Jonathan Melo as “Thought # 3,” Aaron Michael Ray as “Thought # 4” De’Lon Grant as “Thought # 5” and Zion Middleton as “Thought # 6,”). 

Portraying all the characters interacting with Usher during the show, this undeniably talented ensemble also serves as Usher's Greek chorus. 

They share in the execution of the libretto, there to aid, inform, support and warn Usher as various characters as required in the story. 

Yet, they also hurt, berate, insult and condemn Usher as other characters, essentially keeping all aspects of the story in perfect balance. 

A credit to the consummate vision by Parent, the above never becomes overplayed, descending the musical into either the maudlin or, worse, the utterly morbid.

As the “Circle of Life” homage continues, Usher refers to their father as “Mufasa” and mother by “Sarabi,” a not-so-subtle jab at his “Lion King” ushering job. (There are also references to "Nala" and "Scar" but in a very disturbing, "inbred" sort of way.)

(Photo: Kai Clifton as "Usher" in a "spirited" moment with the CAST of Michael R. Jackson's "A STRANGE LOOP" produced jointly by Front Porch Arts Collective and SpeakEasy Stage Company in Boston, MA. until May 25, 2024. Photo credit Maggie Hall Photography)

Like Usher, these “Thoughts” are also stuck in a "LOOP" but seem to focus their demoralizing negative energies on Usher making them feel worse about their appearance and sexuality, even threatening them and making Usher fearful of the risk of HIV or AIDS

Also, in a world admonished for "body shaming" women, in "A STRANGE LOOP," at least for "plus-sized" gay Black men, the musical appears to want to say, "hold my beer, honey" as the height of "obesity intolerance" shown to Usher is off the charts. 

In the musical number, "Boundaries," at what may prove one of the lowest points in the story, Usher, so lonely and isolated, accepts "intimacy" in the form of a white man named “Daddy” who is startlingly abusive during their bizarre liaison. 

(Note: The show does come with a content advisory stating - "contains explicit language (including racial slurs), references to racism, sexual assault, and homophobia, and scenes of an adult/sexual nature.") 

For those who may be struggling with certain mental and/or emotional health issues, there might be some content in the musical like the above which could be considered triggering. 

On a professional level, Usher is offered the opportunity to ghost-write the book for a Tyler Perry Gospel project. 

Usher’s homophobic father asks if Usher has "contracted HIV yet" while his equally homophobic church-going mother avoids the gay talk altogether by instead asking about Tyler Perry’s Gospel play. 

Usher, while not a fan of Perry, is convinced to take on the job. 

So, Usher writes the play and then proceeds to act out all the characters in the song, "Writing a Gospel Play” much to the astonishment of Usher's parents. 

“AIDS Is God’s Punishment” is a satirical song about AIDS and how AIDS is less about God’s “punishment” and more about human shortsighted ignorance and intolerance. 

(Photo: Kai Clifton as "Usher" and the CAST of Michael R. Jackson's "A STRANGE LOOP" produced jointly by Front Porch Arts Collective and SpeakEasy Stage Company in Boston, MA. until May 25, 2024. Photo credit Maggie Hall Photography)

Again, this is not a show that will be enjoyed by everybody and that appears to be almost by design as it seeks not to merely entertain but inform and bring a little reality into a world of fantasy.

The lighting and sound design for the production is top notch and is effectively utilized by the ensemble. There is also some highly inventive costuming involved which allows for fluid changes in rapid time.

By the way, if the above all reads like this musical leans a little heavy...if not teetering...on the completely tragic, it should be noted, once again, that there is an exquisite blend of outlandishly funny material which also permeates much of the story.

By the show’s conclusion, though, "A STRANGE LOOP" insists that everyone has the right to be seen and accepted unconditionally for who they are. 

There was an unexpected surprise for the Boston audience in attendance at the May 1st performance as Michael R. Jackson appeared on stage with the cast and director and heaped praise on everyone associated with this exemplary production. 

(Photo: Director Maurice Emmanuel Parent hugs "A STRANGE LOOP" creator Michael R. Jackson who made a surprise appearance after the curtain call of the May 1st performance of the show in Boston, MA. "A STRANGE LOOP" runs until May 25, 2024. Photo credit Eran Zelixon)

This tremendously talented ensemble brings to the forefront a compassionate musical about a compassionate person attempting to write a musical about compassion.

"A STRANGE LOOP" simultaneously entertains and informs, giving us a heartfelt look at a community whose inhabitants deserve far better treatment from those outside that community.

Produced in collaboration between Front Porch Arts Collective and SpeakEasy Stage Company"A STRANGE LOOP" continues at the Calderwood/BCA at 527 Tremont Street, Boston until May 25th, 2024

See it now before it leaves as one never knows when it might "LOOP" back around again.


Approximately one hour, 40 minutes with no intermission. 

Kevin T. Baldwin is a member of the American Theatre Critics Association (ATCA)




Winner! 2020 Pulitzer Prize for Drama and 2022 Tony Award for Best Musical 

Michael R. Jackson’s blisteringly funny masterwork "A STRANGE LOOP" exposes the heart and soul of a young artist grappling with desires, identity, and instincts he both loves and loathes. 

Meet Usher: a Black, queer writer writing a musical about a Black, queer writer writing a musical about a Black, queer writer.  

Usher wrestles with the thoughts in his head in an attempt to capture and understand his own "STRANGE LOOP."  


SPEAKEASY STAGE COMPANY is a non-profit theatre company located in the South End of Boston and is led by award-winning Producing Artistic Director Paul Daigneault. SPEAKEASY STAGE COMPANY was named the Pavilion Resident Theater for the Boston Center for the Arts in 2007 and produces 28 weeks of new plays and musicals each season at the Nancy and Ed Roberts Studio Theater in the Calderwood Pavilion at the Boston Center for the Arts.