Rep’s ‘Last Five Years’ a Smart Sweet Modern Musical

Milwaukee Repertory Theater presents The Last Five Years in the Stackner Cabaret, March 21 – May 18, 2025. Pictured Asher Muldoon and Grace Bobber. Photo by Michael Brosilow.

Few musicals written in the 21^st century speak directly to the young adults who came to maturity in the 21^st century, confronting and analyzing the domestic realities of how they try to live. One such musical began in Chicago in 2001 and went on to New York and Hollywood versions, not to mention international engagements.

It gains much of its notoriety for what some took as a chronological gimmick in storytelling. But that exploration of the disintegration of a marriage is much more than a gimmick. It allows The Last Five Years at the Rep’s Stackner Cabaret to unfold in smart lyrics and musical-emotional counterpoint. Jamie tells things from his perspective from start to finish while Cathy starts off at the end “Still Hurting” and leaps back to such beliefs in love as “Climbing Uphill.”

Composer lyricist writer Jason Robert Brown based the musical on his own failed marriage – Jamie is a struggling writer at the start while Cathy is a struggling actress — but Brown is also a cultural whiz whipping through musical forms. These include but are not limited to pop, jazz, boogie, Klezmer strains a la Fiddler on the Roof and echoes of Sondheim musicals.

The Last Five Years may feel American Idol-ish in its extended high notes, challenging every singer who attempts them. But its lyrics are punchy, poetic, filled with cultural references and attuned to the emotions of young love and rising and ebbing social fortunes —  funny, sad and immediate in emotional hooks.

The couple only occasionally get together in song, usually at their emotional highs in the middle and at the end. But the Stackner version, intelligent for its space, has them next to each other when emotionally apart. Not all productions do this – the musical lends itself to different styles of how to imagine the characters’ separation and intimacy, different ways for the couple to be aware of each other. These performers play instruments as well as sing.

Here they sit side by side playing the piano and exchanging guitar riffs while a lone musician – the talented Scott Cook – turns his cello into a mournful echo or rollicking background, occasionally using drums as well. While in other productions the score is done with a small orchestra, music director Ryan Touhey and arranger Alex Bechtel have created a magical underride with minimal visible instruments. As much as I enjoyed the cascading notes, my personal feeling would be to devote even more time and space to savoring the lyrics.

Director Kelley Faulkner, known mainly to Rep patrons as a performer, understands the power of body tableaus, the sideways looks to bridge the emotional gaps and the calculated music crescendos to tell the story and build the charm of the performers. Her experience with musical comedy guides the two talents in the leads, both new to Rep audiences.

Asher Muldoon, a great fit with his background in comedy as well as singing, captures the slyness and dilemmas of Jamie. The character’s solos use his Jewish heritage in the witty “Shiska Goddess,” explore the humor and offbeat romance of that heritage in “The Schmuel Song” and he still makes us feel the pain of Jamie’s adulterous wanderings in “Nobody Needs to Know.”

A Mequon native with considerable stage experience, a warm manner and a great smile, Grace Bobber plays Cathy, emphasizing the cabaret style singing. While Muldoon relies more on acting chops within the songs, Bobber throws her body and her heart into the big finishes – the laments, the angry criticism of show business and the happier moods reflected in “I Can Do Better Than That.”

Audiences may best remember how their stage finesse fits the story rather than the estrangement being explored, but both performers impress us in the catchy but difficult songs. The production is also notable for how hidden yet exceptional are the technical crafts involved.

The Last Five Years is suitable for any of the Rep’s stages. This Rep Cabaret, a dinner theater of sorts, has staged lighter plays and several tributes to musical comedy stars and styles, but this one is more current. It should draw a younger crowd than some shows in the past and is well anchored and conceived. While emphasizing the music it lands the emotional domestic blows the original intended.

The Last Five Years at the Stackner will run through May 18 with various times and a menu available at https://www.milwaukeerep.com. 

The Last Five Years Gallery

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Dominique Paul Noth served for decades as film and drama critic, later senior editor for features at the Milwaukee Journal. You’ll find his blog here and here.