Photo by Michael Brosilow
Grace Bobber and Asher Muldoon in The Last Five Years
MilwaukeeRepertory Theater presents The Last Five Yearsin the Stackner Cabaret, March 21 –May 18, 2025. Pictured Grace Bobber and Asher Muldoon
What’s fascinating about The Milwaukee Rep’s current production of The Last Five Years is that it is as conventional as it is unconventional. The musical, playing in the Stackner Cabaret, tells the story of a couple in their 20s, Jamie, a writer and Cathy, an aspiring actress. Set against the backdrop of New York City, the two fall in and out of their relationship, and love, over the course of five years.
However, here’s the catch: Jamie tells his story moving forward chronologically. Cathy, however, tells her story in reverse; from the end of the relationship to the very start of it. And somewhere along the lines, the story meets up in the middle. It’s a fascinating approach to a typical love story. And just fascinating to watch as the storylines cross each other.
Writer and composer Jason Robert Brown based the book on his own failed relationship. And that firsthand personal experience of the ups and downs of love and (eventual) loss makes The Last Five Years resonate for anyone who’s ever been in a relationship.
Still Hurting
The Last Five Years is all told through songs. As Jamie’s career as a novelist ascends, Cathy struggles to find her footing in the acting world. The contrast between the two timelines is starkly illustrated at the very beginning and end; Cathy’s opener, “I’m Still Hurting” from the breakup to Jamie first seeing and feeling excitement in the very funny “Shiksa Goddess” number. Jamie, who is Jewish, has dated many women of his faith (he even names them all). Seeing Cathy for the first time is a revelation.
Stay on top of the news of the day
Subscribe to our free, daily e-newsletter to get Milwaukee's latest local news, restaurants, music, arts and entertainment and events delivered right to your inbox every weekday, plus a bonus Week in Review email on Saturdays.
We know the end. We know the beginning. But love is a process, a journey, with stops—and restarts— along the way for these two. The Rep’s production is so enjoyable to watch given the stellar talents of the two performers and their chemistry onstage. Jamie (Asher Muldoon) and Cathy (Grace Bobber) have very different, distinct personalities and that is what makes their struggles so clearly defined, watching to see if they can make it through all their ups and downs, personally and professionally.
Bobber (a graduate of Mequon’s Homestead High School) soars vocally throughout a challenging score while capturing every aspect of Cathy’s anxiety, struggles and caring for Jamie. Muldoon is a wonder to behold; his combined talents of acting, singing and overall performing make Jamie so fully realized that a look, a gesture elicits laughter from the audience.
In addition, both Bobber and Muldoon play piano and guitar exceedingly well (accompanied by Scott Cook on cello), throughout the show, moving with such ease between the numbers. Director Kelley Faulkner, a talented actress herself, once again showcases her strengths in creating a seamless production of a complex story and timelines. It’s a synergy of talents coming together to create a very enjoyable yet heartfelt look at young love and the effects of time and change on that love.
The Last Five Years is, after all is said and sung, a love story. But like a relationship, it’s one that lingers in memory long after the goodbyes have been said, and the room grows quiet.
The Last Five Years runs through May 18 at the Stackner Cabaret, 108 E. Wells St. Running time: 90 minutes, no intermission. Recommended for ages 12 and up. For more information call the Rep Ticket Office at: 414-224-9490 or visit: milwaukeerep.com
