It’s no secret that our corner of Southeastern Kentucky is home to a fantastic music scene. On the weekends you can take your pick of live music events, and come summertime, Master Musicians Festival draws in crowds by the thousands. You might not know yet however, that opportunities to see live music extend beyond traditional concerts. In fact, Flashback Theater Co., Somerset’s professional producing theater company, boasts that their upcoming production of Jason Robert Brown’s The Last Five Years is practically bursting with musical talent. Local singers Jenny Cleberg and Michael Taylor will be accompanied by accomplished pianist Debby McDonald in this intimate musical. Billy Christopher Maupin, Theresa Jean Kibby, and Renate Dopp, all talented artists in their own right, will serve as the production team. Live music fans are advised to get their tickets now for performances running December 12-20, 2025 at First United Methodist Church.

What is The Last Five Years?

The Last Five Years is a deeply personal account of one couple’s life over the course of five years as they fall in (and out) of love. The musical’s honest exploration of the highs and lows of young love has resonated with audiences across the globe; the show has enjoyed wildly successful runs on and off Broadway, on the West End, and even received a film adaptation in 2014. Critics praise Jason Robert Brown’s dynamic and rich score; which borrows from a range of musical genres including pop, jazz, classical, Klezmer, Latin, Blues, Rock, and Folk. Through the story of one relationship, Brown explores universally compelling themes of love, regret, ambition, and heartbreak.

Meet the Cast

Flashback’s All-star cast of performers includes Jenny Cleberg of Somerset and Michael Taylor of Danville in the leading roles of Cathy and Jamie. Debby McDonald of Somerset will join the cast onstage as their sole accompaniment.

Jenny Cleberg serves as the Director of Choirs and Theater at Southwestern High School. She made her FbTC debut in the spring of 2022 in Mary: Her Story and has since been featured in several productions, including Sweeney Todd: The Demon Barber of Fleet Street, The Thin Place, The 39 Steps, Uncle Vanya, and most recently, The Wickhams: Christmas at Pemberley.

Michael Taylor is delighted to return to Flashback Theatre, trading barber shops for broken hearts after his turn as Anthony in Sweeney Todd. He’s performed everywhere from Dollywood (Victorian Carolers, Dreamland Drive-In, Clifford the Big Red Dog Live) to Six Flags (Disco Inferno), to the high seas with Celebrity Cruises. When not on stage, Michael enjoys pretending he has free time. He thanks Flashback for letting him sing about love in his dream role instead of questionable baked goods this time. #nomorebirdcages.

Debby McDonald is excited to be the pianist for The Last Five Years!  She serves as the pianist/organist for First Presbyterian Church in Somerset.  Previous Flashback credits include accompanist for Sweeney Todd, Mary: Her Story, Pirates of Penzance, and annual Season Announcement Cabarets.  Debby would like to thank her husband Jerry for all his support.

Meet the Production Team

The outstanding production team includes award-winning Director Billy Christopher Maupin of Wayne County, Music Director Theresa Jean Kibby of Somerset, Stage Manager Renate Dopp of Somerset, with set, costume, and lighting design from Sommer Schoch of Russell Springs.

Billy Christopher Maupin returns to the directing chair with FbTC following last season’s incisive When We Get Good Again, Sweeney Todd, and All Together Now! and having appeared in Brother Wolf, The 39 Steps, and The Mousetrap.
His productions of Dave Malloy’s Preludes and Carrie the Musical were met with Richmond Theatre Critics Circle Awards for Best Director of a Musical, while his production of Lillian Hellman’s haunting The Children’s Hour  earned him a Tabby Award for Best Director. His other favorite directing credits include Dog Sees God: Confessions of a Teenage Blockhead  and You’re A Good Man, Charlie Brown (in rotating rep with the same cast; Firehouse Theatre Project); Becky’s New Car (Virginia Repertory Theatre); and A Gender-Reversed Exploration of Macbeth (Richmond Shakespeare). In 2020, he was featured in THE NEW YORK TIMES and THE WASHINGTON POST for his one-man adaptation of The Picture of Dorian Gray which he co-adapted and starred in.
Some of his other favorite acting credits include Reverend Oglethorpe in the Smoke on the Mountain trilogy, the Fool in Twelfth Night,  and Ronald in the world premiere of Austin’s Bridge (co-starring Jeremy Jordan). Billy Christopher is an Associate Artist with Carpenter Science Theatre Company and is the co-founder and Associate Artistic Director Emeritus of 5th Wall Theatre.

Theresa Jean Kibby is an evolving actress with many years of screen and stage experience. This is her first time back as music director since her debut in the position during FbTC’s The Pirates of Penzance in 2019. FbTC Credits: Sweeney Todd (Mrs. Lovett) The Mousetrap (Mollie) All Together Now! (soloist), Rosencrantz and Guildenstern are Dead (Alfred), Rosies: the Women Who Riveted the Nation (Kay), and Little Shop of Horrors (Chiffon). Kibby’s experience also includes numerous film and theater projects with Somerset Community college including Steve Cleberg’s Radio Suspense Theatre series.

Renate Dopp is a veteran stage manager with FbTC and occasional performer. Fave stage management moments include: Count Dracula, Brother Wolf, Sweeney Todd, Every Christmas Story Ever Told (2016 & 2021), Pirates and R&G. Performances include: Mary: Her Story (Elder Mary), Little Shop of Horrors (Voice of Audrey II), A Nightmare on Backstreet (Teddy Crooner), and season announcement cabarets.

Sommer Schoch is the founder and Producing Artistic Director of FbTC. In a decade of Flashback history: she has directed numerous productions; overseen the development of programming that drives artists to develop their skills and talents through masterclasses, workshops, and new play development; and established connections to a community that values experiencing art in our world. Before FbTC, Sommer graduated from Cincinnati’s College-Conservatory of Music with dual Master’s degrees in Arts Administration and Business Administration.

The Last Five Years


by Jason Robert Brown
December 12-21, 2025
Directed by Billy Christopher Maupin
Music Direction by Theresa Jean Kibby
at Somerset First United Methodist Church

Over the course of five years, two twenty-something working artists fall in and out of love in New York City. In this intimate and emotionally powerful musical, both are given the chance to share their side of the story. Cathy tells her story backwards while Jamie tells his story chronologically; the two characters only meet once, at their bittersweet wedding in the middle of the show. 

Performance Dates and Times

Friday, December 12, 7:30 p.m.
Sunday, December 14, 2:30 p.m.
Friday, December 19, 7:30 p.m.
Saturday, December 20, 2:30 p.m.

Ticket Information

Single tickets for each individual production are available for purchase throughout the year at the box office or online. Learn more at https://www.flashbacktheater.co/events/

Purchase online at this link or by visiting the box office in person at 209A E Mount Vernon St. during office hours, or by calling the box office at (888) 394-3282, ext. 1. Box office hours are Tuesday through Friday, 11:00 a.m. – 4:00 p.m.

Single ticket pricing for the 12th Season of Flashback productions will be:

Adults – $23 Advance, $25 Door
Students – $12 Advance, $15 Door
Seniors – $20 Advance and Door

Sponsors

The Last Five Years is brought to you in part by support from our Design Sponsors: South Kentucky RECC, Huffman and Huffman P.S.C., Citizens National Bank, Lake Cumberland Regional Hospital, and Southern Kentucky Eye.

Flashback Theater Co. is grateful to our 2025-26 Starlight Sponsors: Applied Behavioral Advancements, The City of Somerset, Kentucky Tourism Arts and Heritage Cabinet,  and The Shubert Foundation. Spotlight Sponsor: M&W Printing; as well as our Footlight Sponsors: David Daring Rentals,, First & Farmers National Bank, The Weigel Family, United Cumberland Bank, T. Ronald Kidd Trust, and Somerset Community College.

The Kentucky Arts Council, the state arts agency, provides operating support to Flashback Theater Co. with state tax dollars and federal funding from the National Endowment for the Arts.