
When Jason Robert Brown’s The Last Five Years premiered at Chicago’s Northlight Theatre in 2001, it flipped the traditional rom-com musical blueprint on its head. Off came the rose-colored glasses, and what was presented was an intimate, searing, and structurally unique take on the modern relationship, inspired by Brown’s own love and loss. Now, twenty-five years later, this piece, directed by Christina Ramirez, returns to Chicagoland at Oil Lamp Theater in Glenview. The Last Five Years presents the entire course of a relationship between Jamie, a rising author, and Cathy, a struggling actress – from the first hello to the final goodbye – performed by only two actors, who take turns singing their hearts out in this vocally demanding score.
Structure is everything in this show. Jamie’s timeline starts from the high of their first date and moves chronologically, while Cathy’s story begins at the end and moves backward. They meet only once, in the middle, for their wedding, and then move in opposite directions.
Lili Galluzzo, playing Cathy, is an absolute powerhouse. She commands the stage with a voice that can belt to the rafters, packing an emotional punch with every note. Whether she is navigating the comedic neuroses of “A Summer in Ohio” or the crushing vulnerability of “I'm Still Hurting,” she conveys unvarnished emotion that anchors the production's vocal stakes.
As Jamie, Abraham Deitz-Green has an effortless, magnetic charm. From his opening number, he is clearly having fun, schmoozing the crowd and winning the audience over with ease. He infuses the ambitious young novelist with infectious likability. In fact, it makes it hard for the audience to decipher who is at fault more in this relationship, forcing them to question everything, just as the leads do.
Perhaps Cathy is too pessimistic? Years of career letdowns have tainted her perspective on life, and misery loves – needs – company. Maybe she can’t be happy unless Jamie is unhappy too. Or perhaps Jamie was always emotionally unavailable? As his career takes off, does he want to give himself sacrificially to another person, or does he want to be the new, shiny toy on the scene? Maybe he only wants to reap the benefits of love without caring for it. These are the questions the audience is wrestling with thanks to their strong performances.

Lili Galluzzo in THE LAST FIVE YEARS from Oil Lamp Theater.
But while individually the leads command the stage, their chemistry together left something to be desired. The musical’s structure itself doesn’t help much. After all, the majority of the time, they sing alone, interacting only with props. So, the anticipation of them finally being in the same timeline, sharing space, perhaps places an undue burden on the moment. Still, their big song together, which is also their wedding song, felt flat. The same charm that Jamie had when he landed his big break was gone, and the fire that Cathy had joking about Ohio was missing. Given that this was opening night, the chemistry may well evolve as the actors settle into each other’s timing, but in this performance it was noticeably absent. Since that crucial piece wasn’t there, it felt a little as if these characters never truly understood each other from the start. Were they truly lovers or just lines intersecting at a point?
Oil Lamp’s space is the perfect venue for this intimate show. The set really doesn’t need much; the songs are the main course. But the set was a bit of a distraction. Flat panels slid on and off stage to delineate different locations or the passage of time, but they were rather clunky when they were moved, like a stubborn shower door. At other times, Jamie entered from behind the audience, stepping directly in from the street. The sudden opening of the door and the outside light coming in pulled one out of the moment. The scenes that worked best were those which used lighting to direct your focus and shine on Jamie or Cathy as they untangled their vulnerabilities or drew you in with bursts of emotion.
The Last Five Years is a unique art piece, and its story is not for everyone. Can love and ambition mix, or are they oil and water? This untraditional, somber look at relationships offers unflinching moments, lush and playful songs, and questions you have to wrestle with – no doubt why it has found its way into the hearts of many musical theatergoers. Whether you're "Team Jamie" or "Team Cathy," fans of this modern musical will certainly fall in love with Oil Lamp’s rendition, thanks to the dynamic performances of its leads. They perform this high-wire act with skill and vocal precision, bringing this complex story to life with incredible emotional depth.
The Last Five Years plays at Oil Lamp Theater now through July 19th.
This review is proudly shared with our friends at www.TheatreInChicago.com.
Chicago continues to produce some of the most exciting work in the country this Summer, offering a wide variety of plays and musicals, as well as comedy, dance, music, and more. To highlight these productions, The League of Chicago Theatres is publishing its Summer Theatre Guide, which showcases more than 100 productions; not just in Chicago's iconic theatre districts, but also across vibrant suburban communities. From Oak Park to Naperville, Glenview to Des Plaines, theatres across the region offer top-tier performances that make it easier than ever to experience the magic of live theatre close to home.
For additional details about this summer's performances and the Summer Theatre Guide visit the League of Chicago Theatres website, ChicagoPlays.com. Many summer shows will also be available at HotTix.org, Chicago's local, discounted ticketing service.
The following is a selection of notable work playing in Chicago this Summer, organized by location.
A selection of productions playing in theatres located Downtown are:
Brokeback Mountain
Chicago Shakespeare Theater
May 28 – June 28, 2026
When Ennis and Jack take jobs on the isolated Brokeback Mountain, all their certainties of life change forever as they flounder in unexpected emotional waters. This intense tale of a hidden love spans 20 years and is interwoven with soulful, original Country Western songs, performed live onstage.
Eugene Onegin
The Joffrey Ballet at Lyric Opera House
June 4 – 14, 2026
Set against the backdrop of 19th-century Russian society, this cautionary tale follows the enigmatic and aloof aristocrat after his fateful encounter with the earnest Tatiana. Richly layered and deeply human, Eugene Onegin explores the fragility of the human heart and how unspoken words can shape destinies.
Untitled Vampire Play
Lookingglass Theatre Company
June 4-July 12, 2026
This romantic-comedy-meets-horror-story world premiere by Kevin Douglas explores love, commitment, codependency...and, of course, vampires.
Champions of Magic
Studebaker Theater in the Fine Arts Building
June 6 – July 5, 2026
The production that critics have described as 'the most spectacular show,' 'two hours of mind-twisting, logic-defying entertainment' and 'the summer blockbuster of magic shows.'
SUFFS
Broadway In Chicago at CIBC Theatre
June 7– 19, 2026
Direct from Broadway comes the acclaimed Tony Award®-winning musical Suffs about the brilliant, passionate, and funny American women who fought tirelessly for the right to vote.
Kinky Boots
Broadway In Chicago at the James M. Nederlander Theatre
June 9 - 21, 2026
Kinky Boots follows the journey of two people with nothing in common—or so they think. As Charlie and Lola work together to turn a shoe factory around, this unlikely pair finds that they have more in common than they realized.
Iceboy!
Goodman Theatre
June 20 – July 26, 2026
Broadway's brightest star of 1938, Vera Vimm, is at the top of her game. But when she adopts a 40,000-year-old Neanderthal discovered frozen in the Arctic, the spotlight begins to shift. As Iceboy thaws, he unexpectedly becomes a theatrical sensation, inspiring Eugene O'Neill and challenging his legendary mother for center stage.
A Musical Tribute to John Williams & Steven Spielberg
Chicago Symphony Orchestra
June 23, 2026
Celebrate the legendary collaboration between composer John Williams and filmmaker Steven Spielberg. From Jurassic Park and Jaws to Indiana Jones and E.T. the Extra-Terrestrial, the scores born of this 50-year creative partnership have captured imaginations around the world.
Star Wars: A New Hope in Concert
Chicago Symphony Orchestra
June 25 – 27, 2026
Embark on an epic adventure to a galaxy far, far away with Star Wars: A New Hope! Experience the iconic film like never before as CSO performs John Williams' legendary Oscar-winning score live.
& Juliet
Broadway in Chicago at Auditorium Theatre
July 22 - August 2, 2026
Break free of the balcony scene and get into this romantic comedy that proves there's life after Romeo. The only thing tragic would be missing it.
Theatres are located in almost every neighborhood in Chicago. A selection of productions playing throughout Chicago are:
Always...Patsy Cline
American Blues Theater
Playing through June 13, 2026
This musical play, complete with down home country humor and big-heart ed emotion, includes hits "Crazy," "I Fall to Pieces," "Sweet Dreams," "Walkin' After Midnight" and more!
LOKI-The End of the World Tour
Lifeline Theatre
Playing through June 13, 2026
In this World Premiere musical, Loki arrives at Asgard, bringing chaos, comedy, and three monstrous (maybe) children. In an us vs. them world, can we envision a new mythology?
The Targeted
A Red Orchid Theatre at Chopin Theatre
Playing through June 14, 2026
Welcome to the Solidarity and Truth Summit. A gathering of the most persecuted, tortured, and misunderstood people in the entire world. They call themselves Targeted Individuals, and they are victims of a vast and covert program of systematic torture, surveillance, and harassment by global intergovernmental powers.
OCTET
Raven Theatre Company
Playing through June 14, 2026
Hailed by the New York Times as "the most original and topical musical of the year" for its 2019 Off Broadway premiere, this inventive and acutely relevant piece reflects the perils of the digital age.
Antigone
Promethean Theatre Ensemble at The Den Theatre
May 31 - June 27, 2026
A timely production of the classic WW2 era adaptation made all the more relevant by recent local and national events.
Catch As Catch Can
Steppenwolf Theatre Company
June 4 - July 12, 2026
When a prodigal son returns to blue collar New England, his homecoming sets off a spiraling crisis for two families, threatening not only their relationships but their very identities. Spanning hilarity, stunning virtuosity and outright horror, this ferocious Chicago premiere—featuring an all-ensemble cast—must be witnessed to be believed.
As You Like It
Midsommer Flight
June 26 – August 2, 2026
Free outdoor performances of Shakespeare's As You Like It will be presented outdoors in six Chicago Parks District parks – Chicago Women's Park and Gardens, Gross Park, Nichols Park, Kelvyn Park, Winnemac Park, and Touhy Park. Banished from court by her uncle, Rosalind escapes to the Forest of Arden, where she disguises herself as man in order to win over her lover by trying to convince him he should forget her. Audiences are encouraged to come early and bring a picnic to enjoy this free programming.
Hair
Kokandy Productions at Chopin Theatre
July 2 - September 13, 2026
Exploring ideas of identity, community, global responsibility and peace, Hair remains relevant as ever as it examines what it means to be a young person in a changing world.
Marble
Gift Theatre at Copernicus Center
August 2 – August 30, 2026
Marble follows two married couples, Ben and Catherine, and their friends Art and Anne, whose comfortable lives begin to splinter after a shared dream triggers suspicion and desire.
A surreal and haunting exploration of two couples whose lives collide through shared dreams, this production anchors the company's homecoming to the neighborhood where it was founded.
Productions playing in the suburbs of Chicago include:
Nunsense
Drury Lane Theatre
June 10 – August 2, 2026
Get ready to laugh the summer away with nuns from the Little Sisters of Hoboken. This beloved revue, directed by E. Faye Butler, will have you in stitches as the five sisters stage a variety show fundraiser filled with outrageous musical numbers and zany comedy.
A Little Night Music
Marriott Theatre
Playing June 17 – August 9, 2026
Set in 1900 Sweden, A Little Night Music explores the tangled web of affairs centered around actress Desirée Armfeldt, and the men who love her. Amid a flurry of jealousy and suspicion, infinite possibilities of new romances and second chances bring endless surprises. Stephen Sondheim's witty, brilliant masterpiece.
Leopoldstadt
Writers Theatre
June 4 - July 19, 2026
At the dawn of the 20th century, Vienna is the heart of European culture. While an extended family gathers in the elegant Merz home for the holidays, two brothers-in-law passionately debate their conflicting visions for the future of their family and the Jewish people–a tension that will echo through the generations that follow.
The Producers
BrightSide Theatre at Theatre at Meiley-Swallow Hall
June 12 – 28, 2026
Mel Brooks' outrageous musical comedy about two schemers trying to stage the biggest Broadway flop of all time—only to accidentally create a smash hit!
The Last Five Years
Oil Lamp Theater
June 6 - July 5, 2026
This widely beloved show takes audiences on the romantic rollercoaster of Jamie and Cathy as they fall in...and out of love over the last five years.
BEAUTIFUL: The Carole King Musical
Highland Park Players at McGrath Family Performing Arts
July 17 – 26, 2026
Before she was hit-maker Carole King—she was Carole Klein, a spunky, young songwriter from Brooklyn with a unique voice. Beautiful: The Carole King Musical takes you back to where it all began and takes you on the ride of a lifetime.
For a comprehensive list of Chicago productions, visit the League of Chicago Theatres website, ChicagoPlays.com. Available discounted tickets will be listed at HotTix.org.
About Chicago theatre
Chicago theatre is the leader in the U.S. with more than 250 theatres throughout Chicagoland, comprising a rich and varied community ranging from storefront, non-union theatres to the most renowned resident theatres in the country, including 6 which have been honored with Regional Tony Awards, and the largest touring Broadway organization in the nation. Chicago's theatres serve 5 million audience members annually and have a combined budget of more than $250 million. Chicago produces and/or presents more world premieres annually than any other city in the nation. Each year Chicago theatres send new work to resident theatres across the country, to Broadway, and around the world. For more information, visit www.chicagoplays.com.
The League of Chicago Theatres' Mission Statement
Theatre is essential to the life of a great city and to its citizens. The League of Chicago Theatres is an alliance of theatres, which leverages its collective strength to support, promote and advocate for Chicago's theatre industry. Through our work, we ensure that theatre continues to thrive in our city.
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