A Tampa native is stepping into the role of one of literature's most patient women, and audience demand has already pushed Jobsite Theater to add extra performances before the show even opens. Colleen Cherry stars as the title character in Penelope: An Epic New Musical, a one-woman folk-pop retelling of the back half of Homer's Odyssey, running select days and nights from August 21 through September 6 at the Shimberg Playhouse inside the Straz Center for the Performing Arts in downtown Tampa.
The show reimagines the epic entirely from the perspective of Penelope, wife of Odysseus, mother of Telemachus, and queen of Ithaca, who spends two decades waiting for her husband's return while fending off suitors and holding her kingdom together. As reported by Creative Loafing Tampa, Jobsite Theater tapped Cherry for the solo turn as the company closes out its 27th season, and added Saturday matinee performances because of strong audience interest, along with a special preview scheduled for Wednesday night. Tickets start at $50, and the 90-minute production is staged in the Shimberg Playhouse at 1010 N. MacInnes Pl., the most intimate of the Straz Center's five venues, with roughly 98 to 130 seats, according to the Straz Center for the Performing Arts.
A Local Star With Deep Jobsite Roots
Cherry is a Jobsite Theater Artistic Associate with a long history on the company's stages, having previously earned a Theatre Tampa Bay award for her work in The Threepenny Opera and starred in Jobsite's production of LIZZIE, per Jobsite Theater. Promotional character portraits of Cherry as Penelope were photographed by James Zambon ahead of the run. The production is directed by Katherine Yacko, with choreography by Alexander Jones, and features an accompaniment of strings, piano, and drums that underscores the show's folk-pop sound.
Jobsite Theater has operated as the Straz Center's resident independent, nonprofit theater company since producing artistic director David Jenkins co-founded it in 1998, according to 83 Degrees Media. The company's season closer arrives as the surrounding Straz Center complex undergoes a $100 million “Boundless” renovation and expansion along the Tampa Riverwalk, a project adding riverfront dining, outdoor staging, and expanded conservatory space through 2027, as Hoodline has previously reported on the riverwalk overhaul.
Written In Isolation, Now Bound For Broadway Recognition
Penelope was created by Alex Bechtel, Grace McLean, and Eva Steinmetz, and Bechtel has said he began writing the piece during the 2020 pandemic lockdown, while isolated hundreds of miles from his romantic partner, channeling that separation into a musical meditation on solitude, waiting, and self-reliance. The show explores those same themes of loneliness and self-reliance through Penelope's own voice rather than her husband's adventures.
The piece premiered under a tent at the Hudson Valley Shakespeare Festival in Garrison, New York, in September 2023, with actress Tatiana Wechsler originating the title role, according to Hudson Valley Shakespeare Festival. Since then, the show has built serious momentum: it ran at Signature Theatre in Arlington, Virginia, played the 2026 Edinburgh Fringe Festival in the UK, and in February 2026 the American Academy of Arts and Letters named it one of two recipients of the 2026 Richard Rodgers Award for Musical Theater, an honor that comes with funding toward a New York City staging. Jobsite's run marks the show's Southern United States premiere, following that trajectory through some of the country's most prominent stages.
Just weeks before the Tampa opening, Joy Machine Records released the official cast recording, Penelope: Live from Joe's Pub, capturing concert performances in New York City starring co-creator Grace McLean. The same Richard Rodgers Award panel that recognized Penelope this year also honored Bludline: A Hip-Hop Odyssey, a sign of a broader trend among contemporary theater makers reworking Homer's epic through folk-pop, hip-hop, and other modern musical genres, per the American Academy of Arts and Letters.
