He’s young and brilliant. She’s lovely and hopeful. The stars line up for him. The stars cloud over for her. You know how this one goes. Lean into it anyway. The Last Five Years, the current autumn production of Santa Cruz Shakespeare‘s 2026 season, sparkles with insights that bear retelling.
The pungent ache delivered by this sexy two-hander is all too familiar. Career and romance, like oil and epoxy, rarely form an easy bond. In this innovative bit of autobiographical razzle-dazzle, author/composer Jason Robert Brown gives us two eager young things bound for stardom, one a rising novelist, the other a struggling actor. The answer to their prayers, however, spells the death of their dreams.
Living at different speeds, almost different time zones, Jewish intellectual superstar Jamie Wellerstein (Chris Cherin) and his golden-haired “Shiksa Goddess” Cathy (Charlotte Boyce Munson) reveal their separate versions of what happened to their love. Cathy begins at the end, mourning the fact that Jamie has gone. Jamie starts at the very beginning, filled with chutzpah, new love, and a super-sized ego. His star quickly rises while she’s stuck in dead-end auditions.
David Copperfield may have wondered whether he was the hero of his own life, but Jason Robert Brown has absolutely no doubt. His life is all about him, and he’s got the blazing writing chops to prove it. Is it a self-love letter to brilliant guys in a fast lane that allows them extra privileges? A thinly veiled dismissal of women as a generic herd of followers? Yes and yes.
Laura Gordon‘s directing crafts a deliciously tight show, even pulling the music man Luke Shepherd into the act. Armed with his baby grand—and onstage cellist Kristin Garbeff—Shepherd sets the irresistible pulse of jazz, klezmer and show tune romance that underpins the entire glorious creation. Drinking shots with Jamie, rolling his eyes as Cathy crawls and cavorts atop the keyboard he plays at warp speed. Garbeff’s cello weaves in between the joyful piano, adding dark cognac texture into the score.
Compelling musical lines carry the cleverly rhyming, oft-poetic lyrics through 90 minutes of bracing memoirs. Intimately staged by director Gordon and smartly costumed in contemporary style by Austin Blake Conlee, The Last Five Years spirals through this intense love affair, told from front to back, and from back to front. The music delivered by these two weapons-grade singers is up to the intertwining concept.
The amazing Munson soars through her character’s fresh hopes and trashed dreams for true love and a stage career on Broadway. Her radiant face and astonishing voice—Barbra Streisand comes to mind—map every nuance of every lyric. And every epiphany.
“I will not be the girl who gets asked how it feels
to be trotting along at the genius’s heels.”
We already bleed for her.
Written about Brown’s own five-year marriage and breakup, the part of Jamie Wellerstein is richer and showier. Brown lived this story and drives us into both the angst and the arrogance of his grab for fame. To his credit, the playwright doesn’t spare himself completely, showing us just how much of a schmuck he was as he misspent Cathy’s trust. But yeah, he is the hero of his own life.
His surrogate gets the best lines. From his opening song—“Hey! Hey! Shiksa goddess! I’ve been waiting for someone like you”—to his penultimate send-off: “If I didn’t believe in you, I wouldn’t have loved you at all.”
For me, the heart of Jamie’s tale lies in a single, sobering line:
I will not lose, just because you can’t win.
Jamie Wellerstein, rising star and literary hustler, knows when it’s time to exit. If he comes off as heartless, it’s because he has refused to compromise.
By contrast, Brown’s writing for Cathy leans on stereotypes of a small-town girl hoping to make it big on Broadway. Or at least to marry the guy of her dreams. With her girl-next-door beauty and superstar voice, Munson is the perfect shiksa goddess. But the part isn’t written up to Munson’s gifts. Most of the material Cathy is given paints her as an emerging tradwife, content to let her guy soak up the limelight while she surrenders her dreams.
The two actors are well matched, with the soaring, tangible chemistry to create a particularly choice moment—at the exact center of the play—when they declare their love, and wed. And while Munson has the ferocious vocal gift, Cherin knows how to work his Mariah Carey riffs to wring every last morsel of edge, desire, energy, and glitz out of his electrifying role. Crooning, wailing, and whispering his relentless quest for stardom.
Cherin drives the center of this 90-minute auto-memoir, and part of that is due to his half of the play’s chronology.
We first meet Jamie when he’s hot as a rocket. He sweeps us up in his joyful ascent. Cathy opens the show at the end of the relationship. Her song, “Still Hurting,” arguably the finest in the entire piece, is filled with rueful grief. That’s a tough place to begin.
The double, criss-crossing chronology complicates this play just enough to make us lean in. To savor the mis-remembered dreams. To watch the near-misses flicker and glide on the smooth, unfurling waves of Brown’s highly singable melodies.
For me, this play worked on almost every level, enough for me to want to see it twice. Just to savor the songs, watch the gleaming faces, bite down hard on the all-too-human regrets. Anyone who’s ever dumbed down their triumphs for another person’s sake will feel this play in the pit of their stomach.
If you need a huge cast of dozens and an over-the-top happy ending, then you don’t deserve The Last Five Years. It’s for those who don’t mind flinching while they laugh. Applauding while they dry their eyes.
Utterly seductive music, acting, singing. Everything works.*
The Last Five Years, written by Jason Robert Brown and directed by Laura Gordon. At the DeLaveaga Grove through October 3.
*Even better if you spent time on the East Coast.
