Who Are The Characters In It Should Have Been You?

I love the chaotic charm of the wedding world in 'It Shoulda Been You' — the character lineup is what makes the whole thing sing. The core family at the center is the Steinbergs and the Howards: Jenny Steinberg who’s the anxious, long-suffering sister; Rebecca Steinberg the bride; Judy Steinberg their fiercely opinionated mother; and Murray Steinberg their easygoing father. On the other side are Brian Howard the groom, Georgette Howard his very image-conscious mother, and George Howard his steadier father. Beyond the parents and newlyweds, the plot leans on a handful of scene-stealers. Marty Kaufman is Rebecca’s old flame who stirs trouble the morning of the wedding. Greg Madison is the best man with secrets of his own and Annie Shepard is a close friend/bridal party figure who gets swept up in the drama. Albert is the veteran wedding planner who tosses out calming tropes while chaos erupts around him. There are also delightfully comic smaller roles that double up in productions, like Aunt Sheila who sometimes appears with an alternate identity as Mimsy, and Uncle Morty who can also be played as Walt in some stagings. The show blooms because those personalities collide — jealous moms, secret romances, and the wedding-team pros all push the action. Productions have cast the principals in slightly different ways, but the character core stays the same and that’s why the story works as both farce and tender family portrait. I always end up rooting for Jenny and grinning at the chaos the supporting characters unleash.

The character list for 'It Shoulda Been You' is deliciously theatrical and very archetypal, which is why it plays so well. At the center are the two sisters Jenny and Rebecca Steinberg. Jenny is the put-upon sibling who narrates a lot of her discomfort, while Rebecca is the bride whose wedding sets everything off. Their parents Judy and Murray Steinberg create family pressure and comic heat, with Judy often stealing scenes with her blunt observations. On the groom’s side Brian Howard is the man Rebecca marries, and his parents Georgette and George Howard bring a contrasting social vibe to the event. Rounding the cast are the wedding complications: Marty Kaufman shows up with unresolved history, Greg Madison is the best man whose personal life becomes entwined with others, and Annie Shepard is involved in romantic entanglements that add complexity. Albert the wedding planner has witty asides and practical perspective. Productions also commonly use doubling for amusing small parts like Aunt Sheila and Uncle Morty who can morph into Mimsy and Walt, respectively, in some stagings. That compact ensemble gives each production room to emphasize farce, heart, or both. All in all, the roster is small but theatrical, which makes every scene feel crowded in the best way and keeps the jokes and reveals tight and fast.