Review: Raven Theatre Stages The Luckiest, a Play About Love and Family—With an Ironic Title

The Luckiest is the ironic title of a superb play by Melissa Ross, now on stage at Raven Theatre. It’s a play about family, love and relationships and how they matter, even as life takes unfortunate twists and turns. It’s a helpful message in this Covid era, and it’s delivered in an appealing and humane way. Artistic director Cody Estle directs this three-hander with his usual skill, carefully building the drama and bringing out the unique qualities of each character. 

Cassidy Slaughter-Mason and Christopher Wayland play best friends Lissette and Peter. Early in the play, they meet at a boring party and strike up a lively conversation that quickly leads to a friendship that lasts. Cheryl, Lissette’s loving and hovering mom, is played with mom-like authenticity by Tara Mallen. 

Ross builds the story over the course of a dozen two-character scenes, interwoven over past and present, and set in New York City and Vermont over a decade. In each scene, the character pairs—Lissette and Peter, Lissette and Cheryl, Cheryl and Peter—develop their own friendships and interrelationships. 

We learn in scene one that Lissette has a serious illness but Peter keeps her laughing as he helps her plan the party she wants to hold so she can see all her friends. She’s wheelchair-bound but eager for the party to be a success. 

Cassidy Slaughter-Mason and Tara Mallen. Photo by Michael Brosilow.

The flashback scenes portray the decline in Lissette’s condition; she’s determined to have a plan for the course of her life and insists that Peter and Cheryl allow her to make her own decisions, like staying in New York City rather than moving to her mom’s home in Woburn, Massachusetts. She demands that Peter and Cheryl stop fussing over her. It’s an agonizing experience that many families go through in various ways and Ross’ script tells the story with immense humor as well as heart. Lissette’s relationships with her mom and with Peter are filled with anxiety, arguments and plenty of love. 

Near the end of the play, Lissette turns to the audience and tells us in great detail what her condition is like, how her body is changing and how she lives with it. During that 15-minute monologue, the audience is absolutely riveted to the actor on stage. 

The party preparation takes place in an Airbnb apartment in Vermont because of a Vermont law that is crucial to the way Lissette wants her story to end. Mom is there too and wants to be useful. When Cheryl asks Peter to assign her a role to play at the party, he advises her, “Just bring your amazingly delicious lasagna. Two pans, one for the vegetarians.”

The play’s title comes from Lissette’s habit of finding “lucky pennies” in the street and claiming that she’s “the luckiest person in the world.” She sometimes bestows these pennies on special friends, as she does in one scene with Peter. 

Tara Mallen and Christopher Wayland. Photo by Michael Brosilow.

In a followup message after the performance, Raven Theatre tells its patrons how they consulted with the organization and experts on conditions like Lissette’s so that the script, its setting and its performance could be done correctly. These experts worked with Raven from the very beginning of production.

All three actors are totally engaging performers. Lighting design is crucial here because it signals the quick scene changes; Becca Jeffords and Jesse Klug are lighting designers. The wide stage in Raven’s larger theater is a palette for Jeffrey D. Kmiec’s severely simple scenic design, based on bare brick walls and tiered gray flooring. For each scene, the performers bring on one major piece of furniture that defines the space and push it offstage afterwards. Movement consultant is Sam Hubbard. Costume design is by Izumi Inaba. Eric Backus is composer and sound designer. Eve Breneman is voice and dialect coach and succeeds with Cheryl’s Boston accent including the correct pronunciation of her home town of Woburn.

Playwright Ross is a graduate of the playwriting program at the Juilliard School and a member of both the Dorothy Strelsin New American Writers Group at Primary Stages and Labyrinth Theater Company. Her other plays include Nice Girl and Thinner Than Water.

The Luckiest continues through June 26 at Raven Theatre, 6157 N. Clark St. Running time is 90 minutes with no intermission. Performances  are Thursday-Sunday. Tickets are $40 with discounts available; buy them online or call 773-338-2177. Covid protocols require you to show proof of vaccination before entering and wearing a mask over your nose and mouth while you are in the theater building. 

For more information on this and other productions, see

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Nancy S Bishop

Nancy S. Bishop is publisher and Stages editor of Third Coast Review. She’s a member of the American Theatre Critics Association and a 2014 Fellow of the National Critics Institute at the Eugene O’Neill Theater Center. You can read her personal writing on pop culture at, and follow her on Twitter @nsbishop. She also writes about film, books, art, architecture and design.