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Review: IT SHOULDA BEEN YOU at Good Theater

What did our critic think of IT SHOULDA BEEN YOU at Good Theater?

By: Oct. 06, 2025
Review: IT SHOULDA BEEN YOU at Good Theater  Image

Are weddings where people sometimes find themselves “happily unhappy”?  That contradiction and it’s overcoming is at the heart of It Shoulda Been You, the first mainstage production presented at the new home of Portland’s Good Theater.

At a Saturday matinee, the converted high school auditorium on Stevens Avenue proved a warm and comfortable spot to enjoy a slightly twisted musical comedy of recent Broadway vintage directed by Good Theater co-founder Brian P. Allen.

Perhaps a bit familiar to those who enjoy wedding comedies, sibling, parental, financial, religious, ethnic, and various other conflicts are rampant in this play, enlivened by fine performances from a cast of mostly local actors.  The play by Brian Hargrove and Barbara Anselmi supplies them all with plenty of entertaining song and dance moments as well as an abundance of fast-paced laugh lines, all covered with a sweet glace of farce.

Rachel Lotstein plays the central character of Jenny Steinberg, the slightly plump (as her mother constantly reminds her) sister of the bride who finds it hard to admit she wishes it was her wedding.  She accidently calls Marty Kaufman (David Bass-Clark), her sister’s ex-boyfriend and when he races to the wedding, taking the call as “a sign” of, well, something, the fun begins.

Meanwhile, the caustic, Jewish mother of Jenny and the bride is stewing for a confrontation with the groom’s mom, an equally feisty Gentile woman.   Denise Poirier and Lindsay Conrad are, respectively, very funny as they snark and snap at each other while attempting to be “nice.”  They are barely held back by their put-upon spouses, played by Mark Rubin and Steve Underwood.

The bride, played by Colleen Clark, reconnects with ex Marty in a puzzling way while she bonds awkwardly with groom Brian, played by Thomas Ian Campbell.  All the threads are further complicated by the increasing involvement of friends Greg (Nate Stephenson) and Annie (Mikayla Jane).

Lotstein (“Jenny’s Blues”) and Clark (“A Little Bit Less Than”) reveal strong vocal talents among the many fine performances

Secondary roles belong to Marie Dittmer, Jonathan Miele, and Paul Haley, the latter stealing scenes as a wedding planner who always knows just what to say.

The choreography by Betsy Melarkey Dunphy and Keating Babcock mixes traditional stage styling effectively and the musical trio, led by Victoria Stubbs, is on the mark.  The hotel set design by Steve Underwood and Tracy Washburn, costume design by Justin Cote, lighting design by Jamie Grant, and sound design by Cory Macgowan all serve the show well.

A bit of a twist at the end further confirms that quality mainstage entertainment from Good Theater is back.       

It Shoulda Been You runs through Oct. 19.

Photo by Hannah Daly  

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