
Rivendell Theatre Ensemble, Chicago's only professional theater that seeks to advance women through the power of storytelling, announces the cast for the world premiere of Do Something Pretty by Melissa Ross (The Luckiest, Thinner Than Water, Nice Girl, A Life Extra Ordinary), directed by Rivendell favorite, Jessica Fisch (The Firebirds Take the Field, I Wanna F**king Tear You Apart). Do Something Pretty runs May 2 – June 7, 2026, as part of Rivendell's 30th Anniversary Season of new plays.
The 30th Anniversary Season takes place at Rivendell's home, 5779 N. Ridge Avenue in Chicago. Tickets are priced at $28 for previews and $38 for regular performances. Angel and Sponsor tickets are priced $58 and $88 and include a donation. Discounts are available for seniors, students, and military. Tickets go on sale March 23 at rivendelltheatre.org/dosomethingpretty and (773) 334-7728.
Summer of 1992. The United States is in a recession. Arkansas Governor Bill Clinton is about to run for president. Kurt is married to Courtney. Yo MTV Raps is on the TV. And Zach Morris is the only kid with a cell phone.
On a hot August night in a small Massachusetts town the last few weeks before school starts. Three teens try to navigate their way through the murky path to adulthood. Phoebe wants to grow up. Jason wants Evie. And Evie just wants to get as far away from everyone as she possibly can.
Artistic Director Tara Mallen comments, "A few years ago, I was inducted into to the world of Melissa Ross when I was cast in one of her (stunning) plays The Luckiest at Raven Theatre. What struck me most was these complicated, messy, outrageously human women that Melissa centers in all her plays are all portrayed as subjects rather than objects. In 2026, it shouldn't be the case that this is a rarity—but I promise you that it is. So, when Melissa reached out asking if Rivendell might be interested in her brand-new play depicting two sisters—one on the brink of teendom and the other on the edge of adulthood—I jumped at the chance. I am so delighted to welcome Chicago audiences to hearken back to 1992 and bring Do Something Pretty to our stage at Rivendell."
This world premiere production of Do Something Pretty marks ensemble member Katherine Mallen Kupferer's (Phoebe) Rivendell debut. The cast also features Jasper Johnson (Matt), Reilly Oh (Jason) and Jocelyn Zamudio (Evie).
The creative team includes Daira Rodriguez (Assistant Director), Lindsay Mummert (Scenic Design), Saawan Tiwari (Costume Design), Sierra Walker (Lighting Design), Eric Backus (Sound Design), and RTE Ensemble Members Sarah Slight (Dramaturg), and Caroline Michele Uy (Associate Dramaturg). The Production Stage Manager is Rita Vreeland and the Artistic Producer is RTE Member Pat Fries (Artistic Producer).
Rivendell is offering a special mid-season RivPass good for the remainder of its 30th Anniversary Season. The $65 subscription includes a ticket to the 2nd and 3rd mainstage shows. Purchase this offer atrivendelltheatre.org/tickets or by emailing General Manager Trisha Hooper at This email address is being protected from spambots. You need JavaScript enabled to view it..
The Do Something Pretty lead production sponsors are Maureen and Anna Miller. Rivendell's 30th Anniversary Season is sponsored by Sharon I. Furiya.
FACTS / Do Something Pretty
Do Something Pretty
A world premiere by Melissa Ross
Directed by Jessica Fisch
May 2 – June 7, 2026
Cast: RTE member Katherine Mallen Kupferer (Phoebe) with Jasper Johnson (Matt), Reilly Oh (Jason) and Jocelyn Zamudio (Evie).
Creative Team: Daira Rodriguez (Assistant Director), Lindsay Mummert (Scenic Design), Saawan Tiwari (Costume Design), Sierra Walker (Lighting Design), Eric Backus (Sound Design), and RTE Ensemble Members Sarah Slight (Co-Dramaturg), and Caroline Michele Uy (Co-Dramaturg). The Production Stage Manager is Rita Vreeland and the Artistic Producer is RTE Member Pat Fries.
Dates:
Previews: May 2-8, 2026
Saturday, May 2 at 8pm
Sunday, May 3 at 3 pm
Tuesday, May 5 at 8pm
Wednesday, May 6 at 8pm
Thursday, May 7 at 8pm
Friday, May 8, at 8pm
Gala Opening: Sunday, May 10 at 6pm
Press Opening: Monday, May 11 at 7pm
Regular Run: May 15 – June 7, 2026
Thursday-Saturday at 8pm; Saturday at 4pm
Added Performances: Sundays, May 24 and May 31 at 3pm
Open Caption: Thurs May 21 at 8pm; Saturday May 30 at 4pm
Town Halls: Friday May 8, Young Industry Professionals; Saturday May 23 after 4pm performance
Life comes at you fast. We go about our lives, navigating the ups and the downs, never really thinking of more than the day to day, the little irritations of work, or being consumed by a new love. Then, as it always seems to go, something upends our life, like a life threatening illness. Suddenly everything that once consumed our thoughts becomes trivial, eclipsed by the momumentalness of the new reality. While most could succumb to the pressure of such news, others persevere, determined to live their life on their terms, regardless of knowing what lies ahead of them. This very real life scenario played out in Melissa Ross’ 'The Luckiest'.
Lissette and Peter are best friends living their best lives. But when an out-of-nowhere diagnosis shatters Lissette's world, Peter is left trying to pick up the pieces. Suddenly finding herself at odds with her best friend and her mom – who each come bearing strong opinions wrapped in good intentions – Lissette is forced to navigate between the two while unflinchingly forging her own path for her future. This tender, funny, and keenly-observed play explores the uncertain and sometimes heartbreaking territory of how we choose to take ownership of our lives. Melissa Ross’ moving play, full of heartbreak and hilarity makes its Chicago Premiere.
As one who nows cries at every sad or beautiful movie, play, or song, I fully expected to be clutching a tissue all evening while watching The Luckiest. As I watched Lissette, played by Cassidy Slaughter-Mason, and Peter, played by Christopher Wayland, throughout their friendship we see a beautiful complex narrative that forces the question, “who really is the luckiest?” Is the luckiest Lissette, who, despite this life ending illness, chooses her own fate and lives her life unabashedly? Is she the luckiest to have had such a friend as Peter, who helped her navigate her life with the illness? Perhaps the luckiest is Peter, who is lucky to have met and befriended Lissette, lucky to have had him in her life. One could say Lissette’s mother, played by Tara Mallen, is the luckiest to hae been there for her daughter in her time of need. Consider for a moment that the luckiest people are the survivors, Peter and Lissette’s mother, who live on no longer under the weight of caretaking nor bearers of the weight of such a onerous decision. Maybe the luckiest person is the one who chooses to leave this world, no longer in pain or heartache.
The beauty of Melissa Ross’ 'The Luckiest' is that the lucky one is in the eye of the beholder. She holds a mirror to our lives with honesty, grounding, and even a little dark humor. I happen to think that we, the audience, are the lucky ones. We’re lucky to be spectators to such a story, to have our health and ability to see Lisette and hear her words, and walk away from the play knowing we too could have our lives changed at any moment; a reminder to live our lives. 'The Luckiest' is a substantioanlly light play that is sure to stay with you long after you leave the theatre, and we are all the more lucky for it.
'The Luckiest' is playing at Raven Theatre located at 6157 N. Clark Street, Chicago, IL 60660 through June 9th. Tickets are available at https://www.raventheatre.com/stage/the-luckiest/.
Having been wanting to check it out for quite a while, I was excited to go see Nice Girl at the Raven Theatre, the theatre’s latest offering, this one by Melissa Ross and directed by Lauren Shouse. Upon entering the Edgewater located venue, I walked into the warmth and was greeted by two friendly gentlemen. It is an unassuming, no thrills theatre, and unfortunately was missing a bar. As I went to find a seat, I noticed the sense of community at Raven Theatre. It was clear the staff was close-knit and well-connected in the theatre community.
I was immediately transported to Massachusetts as they play started. Both Josephine, played by Lucy Carapetyan, and her mother Francine, who is played by Lynne Baker, show fantastic chemistry from the get go and the banter between the two is strong, to say the least. In fact, their repartee is so realistic at times as they both pushed each other's buttons it made me uncomfortable.
The premise of the play is that Josephine is 37, single, and living with her mother. She befriends a coworker named Sherri (Stella Martin) who happens to be the saving grace of this play. She brings a much-needed energy to the sad life that Carapetyan so convincingly brought to her character. As the play progresses we are introduced to Donnie (Benjamin Sprunger) who is an old classmate of Josephine and they start to build a budding romance. But the characters prove to be bland.
There is a twist in the second half of the play in which I missed completely, most likely due to the lack of interest in the play’s characters. I truly struggled with the play and what it offers to its audience. It is sad and without much hope until the end of the show. What I yearned for was the steady, noticeable growth of Josephine throughout the challenges of her relationship with her mother but again, some changes occurred at the end.
Nice Girl is a bit hard to watch but it does have some humor breaks here and there, albeit on the more minor side – not enough to salvage the play. I struggled with feeling much hope for the main character. If seeing the play, be prepared to be sad and have a lot of hurt in your heart. However, when walking out of the Theatre many patrons commented that they enjoyed Nice Girl, obviously appealing to the taste of several theatre goers. Who’s to say who will enjoy what so, as always, check it out and make your own opinion.
Nice Girl is being performed at Raven Theatre where it is running until March 11th. Tickets available at www.raventheatre.com.
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