Another unique entertainment option at The Winter Park Playhouse is our Spotlight Cabaret Series in the beautiful lobby piano bar. Different professional singers are featured in this monthly series and the New York-style cabaret performances are approximately 55 minutes in length with no intermission. Tickets for this very popular offering are $20. Students must be 15 years of age or older to be admitted to our cabaret series.  
Tickets for this very popular offering are $20 with a one drink minimum. Advance reservations and early arrival are strongly recommended as seating is limited to 72. Tickets can be purchased online or by visiting or calling the box office at (407) 645-0145. Once sold-out, standing room tickets are available for $10. 


Johnathan Lee Iverson

The Last Ringmaster
A Musical Journey from Choirboy to the Big Top

Live performances at the Playhouse: May 18 & 19, 2022

Virtual encore viewing: June 3-5, 2022

Johnathan Lee Iverson brings his commanding presence and noteworthy professional vocals to his new solo cabaret, The Last Ringmaster: A Musical Journey from Choirboy to the Big Top, premiering at The Winter Park Playhouse in the Spotlight Cabaret Series on May 18 and 19, 2022. Playhouse Musical Director Christopher Leavy will accompany on piano.

Fresh off of The Winter Park Playhouse Critic's Choice production run of Trav'lin: A 1930's Harlem Musical Romance, Johnathan Lee Iverson will grace the Playhouse Cabaret stage with a remarkable evening of song and storytelling. From his youthful days with The Boys Choir of Harlem to his notable historic tenure as Ringmaster of the original Ringling Bros. and Barnum & Bailey Circus, Johnathan will delight the audience with a wide selection of music from opera (Turandot, Fedora) to standards (Duke Ellington) to Broadway (Jekyll and Hyde, Man of La Mancha, Sideshow) and more!

Mr. Iverson has had a storied career in entertainment. For this special evening, he will invite one and all to travel with him through a musical odyssey of a boy with a dream, who lives a life bigger than he could have ever imagined. Johnathan will not only weave a riveting tale of his journey, but also perform a wide range of vocal selections that will showcase his performing excellence.

Locally, Johnathan has graced The Playhouse stage in both Crazy For Gershwin and Trav'lin and was voted Broadway World's best actor for his portrayal of Reverend Moore in A Tennessee Walk (Garden Theatre). He has also been a featured performer with Opera Orlando. Johnathan serves as Board Chair for Omnium Circus, has been named one of Barbara Walters' 10 Most Fascinating People, and has even been a question on JEOPARDY!

"We are so thrilled that Johnathan has chosen to debut his new solo cabaret at The Playhouse! His outstanding talent along with his fascinating life stories and charm guarantee an extraordinary evening." —Heather Alexander, Playhouse Executive Director

General admision tickets for live cabarets are $20 plus a one drink minimum.

The cabaret will take place in the theatre on the mainstage. Assigned seating is limited and performances sell out quickly, so advance reservations are strongly recommended.


The live cabaret will be filmed and available to enjoy virtually June 3-5. Virtual tickets are $20 and can be purchased by clicking below. The private link and password to view the performance will be sent via email on Friday, June 3rd at 5pm.

If you have any questions regarding this purchase, please call our Box Office at 407-645-0145 and we will be happy to assist you.


Anastasia Remoundos

Sing Happy!

Virtual encore viewing: May 6-9, 2022

Anastasia Remoundos brings her dynamic vocals to a brand new solo cabaret, Sing Happy!, in The Winter Park Playhouse Spotlight Cabaret Series. Ms. Remoundos will delight audiences as she shares the story of her life and love for musical theatre. Anastasia will perform well-known Broadway hits from blockbuster productions like The Light In The Piazza, 110 In The Shade, My Fair Lady and Flora and the Red Menace, as well as songs from popular recording artists like Carole King, Lady Gaga and much more!

The virtual encore of Sing Happy! is May 6-9, 2022. Tickets are $20 per person viewing the performance. A link to the recorded performance will be sent to the patron's email on file.

The performance link will be sent Friday, May 6 at 5pm and will be valid through Monday, May 9 at 5pm. If you have any questions regarding this purchase, please call our Box Office at 407-645-0145 and we will be happy to assist you.