The Last Five Years is a Heartbreaker

Photo by Kyle Anne Grendys

Jason Robert Brown’s The Last Five Years is an intimate, emotionally charged two-person musical that feels deeply personal—because it is.

No need for a spoiler alert. We know it’s a breakup story one line into the show’s opening song, but there are plenty of beautiful moments on the way through Brown’s tragic love story, not to mention a certain braveness inherent in a production with two actors singing for almost ninety minutes about hope and heartbreak.   

A quick search will tell you that Jason Robert Brown wrote The Last Five Years as a way to process the emotions surrounding the breakdown of his first marriage. The story is deeply personal—so much so that his ex-wife sued before the show even opened, leading to a last-minute change in the score.

The musical opened in early 2002, starring Sheri Rene Scott and Norbert Leo Butz, but ticket sales were slow, partly because audiences were hesitant to return to theaters after 9/11. The music, however, was fabulous, so the album became a hit. Theater nerds fell in love with the show and have been going to small theaters around the country to watch Kathy and Jamie fall in love—while simultaneously breaking up—ever since.

How does one fall in love while simultaneously breaking up, you ask? Love is complicated, and so is this show–but its structure is brilliant. The Last Five Years is essentially a He Said/ She Said story, with his narrative moving forward through time while hers unfolds in reverse. Brilliant but complicated—and tough to pull off on stage.

Karaline Feller plays Kathy, an aspiring actor making her way backward through this anti-love story. Like so much about The Last Five Years, the role is exceptionally challenging. Unlike many musicals that begin with a stage-setting intro number—think Hamilton—or an ensemble village song—think every Disney musical—The Last Five Years opens with Still Hurting, a heartbreak-fueled, gorgeously devastating ballad that begins with Kathy finding a breakup letter from her husband Jamie that reduces her to tears within the first five minutes of the show. The good news? For Kathy, the night gets progressively better. The bad news? We all know how the story ends.

While Kathy grapples with the end of her marriage, Jamie, played by Jeff Pierpoint, is having an unbelievably good night. In Jamie’s opening song, Shiksa Goddess, he’s 100% sure he’s met the woman of his dreams. Like any boy in love, he bounds around the stage, but the irony is we know he’s singing about the woman we just watched turn into a human puddle. After Kathy explodes in frustrated anguish with her second song, See I’m Smiling, Jamie—an aspiring author in his early 20s—finds out in Moving Too Fast that he has just sold his first book. In the dizzying back-and-forth, Kathy painfully falls in reverse, growing steadily more hopeful with each passing song, though we all know there’s a lot that will go wrong along the way, while Jamie leaps forward into a future we all know is doomed.

By design, the dueling narrative’s emotional pendulum swings brilliantly between extremes—with extraordinary music and raw performances.

Kalliope and Co’s The Last Five Years is, by all indications, a labor of love. Feller, Pierpoint, and the show’s director Brent Ervin-Eickhoff are graduates of Ball State’s theater program, and it’s a safe bet they’ve dreamed since college of putting on Jason Robert Brown’s deeply personal musical masterpiece in a city with a theater scene that prides itself on intimate venues and upstart productions. So, despite the imminent heartbreak, it’s impossible not to root for this show.

Under Ervin-Eickhoff’s capable direction, Feller’s strong voice and Pierpoint’s boundless energy shone through despite the press opening’s rocky start. The stage design, with the infamous breakup letter hanging over the table in the couple’s apartment, proved a perfect set on the Rivendell stage. Harper Caruso’s skilled music direction of Brown’s challenging score, with her leading the way on the piano, served the production well.

Though there were bumps along the way during the first performance, the opening weekend hopefully gave the cast and crew a chance to smooth things out.  

It’s been nearly 25 years since The Last Five Years first premiered in Chicago, yet its themes of love, ambition, and heartbreak still resonate. With this latest revival at Rivendell Theatre—alongside the recent Broadway production starring Nick Jonas and Adrienne Warren—we’re reminded that some stories, no matter how painful, remain timeless.

Between the 82 minutes of stunning music and the emotional rollercoaster of its dual timelines, there are plenty of reasons to see The Last Five Years. 

Just maybe don’t make it your Valentine’s date night.

The Last Five Years runs through February 23 at The Rivendell Theatre, 5775 N. Ridge Avenue, Chicago. You can get tickets here. For more Chicago reviews or show information, see chicagoonstage.com or theatreinchicago.com.

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