
An emotionally powerful and intimate musical peppered with humor, The Last Five Years tells the bittersweet tale of a five year relationship between two young artists.
The storytelling is non-linear: Cathy (Jessie Hoffman), a struggling actor, starts her account at the end of their marriage, working backwards through the timeline. Jamie (Christian Shaw), a literary prodigy, begins his story at the onset of their relationship. The two narratives intersect on their wedding day before diverging again to arrive at the beginning—and end—of their five years together.
With a soaring score by three-time Tony Award-winning playwright Jason Robert Brown (Parade, Bridges of Madison County), The Last Five Years has captivated audiences since its premiere at Chicago’s Northlight Theatre in 2001. It was cited as one of TIME Magazine’s “10 Best” directly following its debut and received Drama Desk Awards for Outstanding Music and Outstanding Lyrics that season. It was later directed by Brown in a record-breaking Off-Broadway run at Second Stage Theatre in New York City in 2013.
This production of The Last Five Years is directed by Kim Wise with music direction and musical accompaniments by Shaw. The pair most recently worked together in the same capacity for Bay Street Players’ acclaimed production of tick, tick…BOOM! in January 2023.
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A SPECIAL MESSAGE FROM
JASON ROBERT BROWN
CREATOR OF THE LAST FIVE YEARS
MEET THE CAST · JESSIE HOFFMAN
Catherine Hiatt

Jessie Hoffman is excited to make her debut with Bay Street Players at the State Theatre in the dream role of Cathy in The Last Five Years.
She completed studies at the New York Film Academy in New York, NY, majoring in its Musical Theatre program, and she is a recent graduate of Valencia College, Orlando, FL. She is currently pursuing a BFA in Musical Theatre and Dance at Rollins College, Winter Park, FL.
Hoffman is a seasoned actor in the region with credits including: The Addams Family (Wednesday Addams), You’re a Good Man, Charlie Brown (Snoopy), Seussical the Musical (Gerturde McFuzz), Shrek the Musical (Princess Fiona), The 25th Annual Putnam County Spelling Bee (Olive Ostrovsky), Urninetown (Little Sally), Reefer Madness (Mary Lane), The Sound of Music (Maria), Little Shop of Horrors (Audrey), and Next to Normal (Natalie).
Notably, Hoffman was selected by the original Broadway cast of The Addams Family as the winner of the “Are You an Addams?” contest.
As a director, she has produced: Annie, The Addams Family, Young Frankenstein, Into the Woods, Hair, 13 the Musical, Peter Pan, The Wizard of Oz, Alice in Wonderland, Seussical, Willy Wonka, and many musical revues she wrote and conceptualized herself. As an educator, has taught at various camps and children’s theatre programs.
When she’s not onstage, Hoffman writes children’s books under the pen name “JD Addams.” You can find out more about her upcoming books and where to purchase them by visiting jdaddamsbooks.com and more about theatrical career at jessiehoffman.com.
Thank you to mom and dad for your endless support.
MEET THE CAST · CHRISTIAN SHAW
Jamie Wellerstein

Christian Shaw is a multi-instrumentalist singer-songwriter based in Denver, CO. Growing up in Gainesville, FL, he got into theatre by playing guitar for pit orchestras and simply never left the world of musical theatre.
He is unspeakably thrilled to perform in this production of The Last Five Years; it has been his favorite musical since he first heard it over ten years ago. He is not only leading this production as Jamie Wellerstein, but also serves as Music Director and personally played every instrument of the accompaniment score you will hear in this production.
Shaw was most recently see on the State Theatre’s stage as Jonathan Larson in tick, tick…BOOM!, January 2023, for which he received the Dolly Award for Best Lead Actor in a Musical of Bay Street Players’ 48th Season—under the direction of Kim Wise!—and also served as Music Director and accompanist.
Other recent credits include: Jesus Christ Superstar (Jesus Christ), The Adventures of Huckleberry Finn (Tom Sawyer; award recipient, Supporting Actor in a Musical, Gainesville Community Playhouse), and Matheson in a darling little musical called The Old Man and The Old Moon, for which he was also Music Director. Additionally, Shaw was Music Director and accompanist of the performance at Bay Street Players’ annual gala, PLAY YOUR PART, in March 2023. Shaw’s band Full Corn Moon and his debut album of the same name are available on all streaming platforms.
He is so proud to be back with Bay Street Players and to have the opportunity to share this beautiful, challenging, and complicated love story with the people of Central Florida.
He would like to thank the partons of Bay Street Players for keeping theatre alive in this strange and changing world; the Vatter family for their seemingly endless hospitality; Kim Wise for her effortless collaboration; and, most of all, his counterpart Jessie Hoffman for portraying—and absolutely destroying—his most favorite role in the canon of musical theatre.

Bay Street Players’ Colorado connection:
Christian Shaw ready for ‘Last Five Years’
by Matt Palm
Christian Shaw is all over the place. Well, no, actually he’s here in Central Florida preparing to open The Last Five Years for the Bay Street Players in Eustis. But the Coloradan who grew up in Florida has traveled between the states so often that even he is getting confused. “When I’m in Colorado, it feels like I’m from Florida,” he says. “When I’m in Florida, I feel like I’m from Colorado.”
But when he’s acting onstage, he feels like he’s in just the right spot. “It’s been so fun to dive into that craft,” Shaw says. “I’m blessed to have continuous opportunities to grow.”
Many of those opportunities have come from the Bay Street Players, where Shaw last year performed and served as musical director for the company’s annual gala. He also has been musical director and starred in tick, tick…BOOM! at the Players’ State Theatre twice, picking up a Dolly Award for Best Lead Actor in the Players’ annual honors.
Not bad for a guy who lives 1,800 miles from the theater.
Click here to continue reading Matthew J. Palm’s feature on Christian Shaw and coverage of The Last Five Years in the Orlando Sentinel.
A NOTE FROM KIM WISE
Director, The Last Five Years
If you were to ask any musical theatre actor to list their favorite shows, The Last Five Years is likely to be among them. It is the perfect combination of beautiful music and lyrics with a timeless, albeit warped, storyline.
We all know that there are two sides to every story, yet the truth lies someplace in the middle.
This show gives us the story of a five year relationship, simultaneously told from both perspectives. Through them, we learn of each person’s struggles, joys, and perceptions of how their time with one another played out. It’s up to us to decide what is true.
It is my good fortune to work with the magnificently talented Christian Shaw once again as Jamie, and I am pleased for him to have also taken on the role of Music Director, in which he personally recorded our beautiful accompaniment tracks. Cathy is played by Jessie Hoffman, a newcomer to the State Theatre. Her amazing voice and subtle, nuanced interpretation of the role is enthralling. Together, their work and commitment to this show makes my part in guiding them seamless.
The support staff of Bay Street Players is, as usual, incredibly accommodating and professional. Each time I work here I feel as though I am at home. Each show makes me love this theatre and its community more.
I look forward to welcoming you to the historic State Theatre and sharing this beautiful story with you.
Kim Wise
Director, The Last Five Years
About the Composer
JASON ROBERT BROWN

JASON ROBERT BROWN is the ultimate multi-hyphenate: an equally skilled composer, lyricist, conductor, arranger, orchestrator, director and performer. A three-time Tony Award-winner, he is best known for his dazzling scores to several of the most renowned musicals of our time, including the generation-defining, The Last Five Years; his debut song-cycle Songs for a New World; Bridges of Madison County, based on the celebrated novel of the same title; and the seminal Parade, for which he received the 1999 Tony Award for Best Score and the 2023 Tony Award for Best Revival of a Musical.
The Last Five Years was cited as one of TIME Magazine’s “10 Best of Everything” in 2001, immediately following its premiere at Chicago’s Northlight Theatre, and received Drama Desk Awards for Outstanding Music and Outstanding Lyrics the same year. It was later directed by Brown in a record-breaking Off-Broadway run at Second Stage Theatre in New York City in 2013.
Brown has been lauded as “one of Broadway’s smartest and most sophisticated songwriters since Stephen Sondheim” (Philadelphia Inquirer) and for his “extraordinary, jubilant contributions to musical theater” (Chicago Tribune.)
Brown studied composition at the Eastman School of Music in Rochester, NY and lives with his wife, composer Georgia Stitt, and their daughters in Nyack, NY. Brown is a proud member of the Dramatists Guild and the American Federation of Musicians.
BEHIND THE MUSIC | THE LAST FIVE YEARS
with JASON ROBERT BROWN
A NOTE FROM HECTOR DE LEON
President
Bay Street Players’ Board of Directors
It’s true that The Last Five Years is not presented as often as it deserves to be by community theatres such as ours; it is difficult in many ways.
With a cast of only two young actors left barren and alone—literally and metaphorically—to convey a valley of complex emotions through song, there is nothing to hide behind. The pair tasked with taking on these roles are in some of the most challenging positions out there. In this way, we are unspeakably lucky to have Christian Shaw and Jessie Hoffman on our stage to offer deeply insightful interpretations of these stories.
Separately, they make us believe them, root for them. Akin to a debate stage, they have us alternating between whose side we’re on until their last words, and somehow we might still be left torn—this is no easy feat.
Hector De Leon
President
Bay Street Players’ Board of Directors
FROM THE ARCHIVE
Review: The Last Five Years
by Hedy Weiss
CHICAGO SUN-TIMES
Originally published May 25, 2001
It takes only two songs–the very first two in the show, in fact–to make it clear that Jason Robert Brown’s new 80-minute musical, The Last Five Years, is a very special piece of work.
It’s instantly clear, as well, that this poignant, richly dramatic and piercingly honest two-character show is destined to be a hit–and not only at Northlight Theatre, where it received its crystalline world premiere Wednesday night.
This is a piece that will challenge every pair of young musical theater performers willing to wear their broken hearts and bruised egos on their sleeves, if they also are able to meet the formidable vocal demands of Brown’s lushly melodic music and his strikingly colloquial yet glittering lyrics.
But about those two opening songs, and the people who sing them.
She, Kathleen [later changed to Catherine/Cathy], the tall, slim, leggy Irish girl, is first glimpsed standing in front of boxes packed with the detritus of a brief marriage. Still awash in the pain and hurt of failed love, she sings of her anger and loss.
He, Jamie, is first caught preening, as if he were already preparing for his next girlfriend. Yet as it turns out, we are catching him at the very moment when he fell head over heels for Kathleen, five years earlier. There he is, an intensely verbal, self-deprecating and at the same time narcissistic Jewish boy in classic Philip Roth mode, begging to be struck with “the ancient curse of shiksa queens.”
Like a youthful, latter-day Roth, Jamie is a novelist. And at the age of 23 he is quite full of himself, having just landed an agent and a book deal at a major New York publishing house, as well as the girl of his dreams. (Any resemblance to the gifted Brown is not entirely coincidental; he nabbed a Tony Award for the musical “Parade” before he turned 30.)
Like 95 percent of the young aspiring actresses in New York, Kathleen is beset by rejection–repeatedly making a hash of her singing auditions and stuck in summer-stock productions in Ohio. Her confidence level is at zero.
Though one of them is totally self-involved and the other is self-deflated, they love each other madly and marry. But as the ingeniously employed revolve in the stage floor suggests, they start to spin in opposite directions.
The meticulously woven, time-warped structure of Brown’s cyclical show–love in its first thrilling bloom counterpointed with love in aching retrospect–is beautifully conveyed in those initial songs. And under the impeccable direction of Daisy Prince (whose father, veteran Broadway director Hal Prince, was among the opening night crowd), every visual
element of the production reinforces it.
Designer Beowulf Boritt has devised a powerfully poetic set–the upended room of a wedding party, with chairs and wedding flowers at right angles to the stage floor, and the shattered foundations of the marriage lying in a pile. Think of it as a tiered, toppled wedding cake, too, or as a clock ticking off the moments in opposing directions.
The performers, backed by musical director Tom Murray and Brown on piano as part of a six-piece backstage orchestra, are splendid. Butz (the emcee here in the national tour of “Cabaret”) captures the energy, drive and urban sharpness as well as the charm and selfish childishness of Jamie. And Brown has given him a great gift in a brilliant song that unspools as a parable about a shtetl tailor–a gift that he translates into sublime theatrical magic.
Kennedy embodies the endearing mix of all-American beauty and gawkiness that clearly captivates Jamie, and turns Kathleen’s wedding vows scene (staged on a Central Park rowboat) into a deeply moving expression of the character’s insecurity and innocence.
All these scenes may sound familiar. But Brown’s lyrics—alternately cutting and boldly romantic—sweep the stage like a summer storm. There is little protective irony here; only the sharp pain of young but damaged hearts.