Early next month, Emmy- and Halo Award-winning artists — several with Wilton ties and family connections — will be staging a new production of Jason Robert Brown’s The Last Five Years for two nights only at the Wilton Playshop.

Eight-time Emmy award-winning director and a two-time Director’s Guild of America honoree Joe Michaels will be directing. The former Wilton resident was the director of NBC’s “Today” show for 20 years and began his career in television as an associate director and director for NBC Sports. His work on other Emmy-winning telecasts includes the World Series, the Super Bowl, Wimbledon Tennis, and the Olympics, among many others, and he has directed commercials, stage productions, and special events.

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Manhattan-based singer/actress/puppeteer Natalie Michaels will play ‘Cathy Hiatt’. The Wilton native (and Joe’s daughter) said she’s honored to take a role she calls one of her all-time favorites “in the theater that practically raised her.” Her most recent work includes performances with The Very Hungry Caterpillar Show, both off-Broadway at DR2 and on the national tour; and on YouTube with “The World of Eric Carle” series. Natalie has also had residencies as a cabaret singer with the Rose Room in New York City and at the Greenbrier Resort in West Virginia.

Wilton resident Sarah Lee Michaels is the show’s musical director (as well as Natalie’s mom). Sarah has made a career in performing arts on both sides of the stage over the last 30 years. She has performed in local, regional, and Off-Broadway theaters as a singer/dancer/actor, and as a musical director, producer, choreographer, and vocal coach in Connecticut. Recent productions include Wizard of Oz (as musical director); and Evita, Art, [title of show], Lion in Winter, and Jekyll and Hyde (as producer). Sarah is the current executive producer of the Wilton Playshop. She owns the Voice Studio of Performing Arts in Wilton and is the artistic/musical director of Break A Leg Productions, LLC, a youth musical theater training program formed with colleague Christine Titus in 2022.

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Halo award-winning actor and Wilton resident Dayo Garritano will star as ‘Jamie Wallenstein.’ Garritano has been singing and acting since he was in fifth grade and is excited to make his Wilton Playshop debut in The Last Five Years. He earned a Halo Award for Best Lead Actor in a Musical for his portrayal of ‘Archibald Craven’ in The Secret Garden, and has performed at Carnegie Hall three times and Lincoln Center once. Garritano received the Musical Theater Scholarship from Interlochen Arts Academy where he studied musical theater for three years, is an alumni of Wooster School in Danbury, and is currently getting his BFA in acting at the University of Connecticut.

Emmy award-winning artist Robyn Mola is the audio and lighting engineer on the project. As a mobile TV engineer, Mola has worked with WWE, Turner Basketball, Fox NFL, Australia’s “The Voice,” and Australia’s “Ninja Warrior,” and in 2020, she won a Daytime Emmy for her work on “The People’s Court.” She now serves on the board of Rising Stars Performing Arts in Norwalk as their technical director.

Drama Desk winner The Last Five Years ingeniously chronicles the five-year life of a marriage. This one-act modern musical has been translated into a handful of languages and was named one of Time Magazine‘s 10 best shows of 2001. A testament to the show’s longevity, and spurred by the show’s regional popularity, The Last Five Years enjoyed an Off-Broadway revival at Second Stage in 2013 and a film adaptation was released in 2014, starring Anna Kendrick and Jeremy Jordan.

An emotionally powerful and intimate musical about two New Yorkers in their 20s who fall in and out of love over the course of five years, the show’s unconventional structure consists of Cathy, the woman, telling her story backward while Jamie, the man, tells his story chronologically; the two characters only meet once, at their wedding in the middle of the show.

It’s a poignant show that will leave audience members speechless. The show will only run Friday, June 2 at 8 p.m. and Saturday, June 3 at 8 p.m. at the Wilton Playshop (15 Lovers Ln.). All tickets are $20 and are available for purchase online.