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| | The Pin Up Girls
March 20 - March 29 & April 9 - 25, 2026
Previews: Mar. 19 at 7:30pm & Mar. 20 at 2:00pm
By James Hindman and Jeffrey Lodin
The performances of The Pin-Up Girls will take place in the Mandell Theater at Orlando Shakes located at 812 E. Rollins Street, Orlando, FL 32803.
Regional Premiere! From The Andrew Sisters to Hip-Hop and Gershwin to Beyoncé, The Pin-Up Girls sing a cavalcade of hits inspired by letters home from our troops overseas! While singing at the local VFW hall, the ladies stumble upon a huge stash of letters that date back 100 years. Inspired by what they find - funny, sexy, romantic and poignant - they put on a show that celebrates the men and woman who fight to defend out country.
"The show is a wonderful piece of entertainment. Memorable music, comedic characters and excellent performances." -Broadway World
This production is suitable for all audiences. Age Requirements: Ages 15 & older.
NO LATE SEATING.
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| | Spotlight Cabaret Series
featuring Kevin Kelly - LIVE
LIVE DATES:
March 25 & 26, 2026 @ 7:30pm
Local Treasure Kevin Kelly debuts his latest solo cabaret in The Winter Park Playhouse Spotlight Cabaret Series. Mr. Kelly will delight audiences with his cabaret evening full of standards! Cabaret audiences will love Kevin's renditions of classic songs from the collection of legendary performers and composers such as Tony Bennett, Duke Ellington, Frank Loesser, Johnny Mercer, Bobby Darin and Dean Martin.
Playhouse Patrons will remember Kevin from his numerous Playhouse cabarets and Mainstage performances including Murder For Two, Ruthless!, The Musical of Musicals and more! Musical Director Christopher Leavy will accompany on the piano. These popular cabarets sell out quickly so get your tickets today!
This unique form of entertainment showcases a different professional singer each month. A truly "New York-style" cabaret, each performance is approximately 55 minutes in length with no intermission. Doors open at 6:30pm for seating.
This production is suitable for all audiences. Age Requirements: Ages 15 & older.
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| | Stage to Screen!
Featuring Natalie Cordone & Shawn Kilgore
Wednesday, April 1, 2025
2:00pm & 7:30pm
A One-Night Only Fundraising Event
This 90-minute musical celebration of Broadway and movie musicals features the dynamic vocal duo of Natalie Cordone and Shawn Kilgore with their swinging trio of jazz musicians. The singing pair met years ago while performing on The Playhouse Mainstage in the Tony Award-winning musical Baby. This dynamic show promises an unforgettable experience where the magic of Broadway meets the enchantment of Hollywood. Net proceeds will go to support the quality musical programming on the Playhouse Mainstage and out in the community Tickets are only $65. Get yours before we sell out!
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| | Spotlight Cabaret Series
featuring Kevin Kelly - VIRTUAL CABARET
VIRTUAL DATES: Apr. 10 - 13, 2026
Local Treasure Kevin Kelly debuts his latest solo cabaret in The Winter Park Playhouse Spotlight Cabaret Series. Mr. Kelly will delight audiences with his cabaret evening full of standards! Cabaret audiences will love Kevin's renditions of classic songs from the collection of legendary performers and composers such as Tony Bennett, Duke Ellington, Frank Loesser, Johnny Mercer, Bobby Darin and Dean Martin.
Playhouse Patrons will remember Kevin from his numerous Playhouse cabarets and Mainstage performances including Murder For Two, Ruthless!, The Musical of Musicals and more! Musical Director Christopher Leavy will accompany on the piano. These popular cabarets sell out quickly so get your tickets today!
This unique form of entertainment showcases a different professional singer each month. A truly "New York-style" cabaret, each performance is approximately 55 minutes in length with no intermission.
This production is suitable for all audiences. Age Requirements: Ages 15 & older.
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| | Spotlight Cabaret Series
featuring Tonya Phillips Staples - LIVE
LIVE DATES:
April 22 & 23, 2026 @ 7:30pm
Tonya Phillips Staples debuts in The Winter Park Playhouse Spotlight Cabaret Series with an original solo cabaret. Join Tonya for an exciting evening of story and song.
Patrons will remember Ms. Staples from her Playhouse debut in The Bikinis. She also appeared in Sounds of the World, a Playhouse collaboration with Barbara Chandler Productions. Musical Director Christopher Leavy will accompany on the piano. These popular cabarets sell out quickly to get your tickets today!
This unique form of entertainment showcases a different professional singer each month. A truly "New York-style" cabaret, each performance is approximately 55 minutes in length with no intermission. Doors open at 6:30pm for seating.
This production is suitable for all audiences. Age Requirements: Ages 15 & older.
| Buy tickets |
| | Spotlight Cabaret Series
featuring Tonya Phillips Staples - VIRTUAL CABARET
VIRTUAL DATES: May 8 - 11, 2026
Tonya Phillips Staples debuts in The Winter Park Playhouse Spotlight Cabaret Series with an original solo cabaret. Join Tonya for an exciting evening of story and song.
Patrons will remember Ms. Staples from her Playhouse debut in The Bikinis. She also appeared in Sounds of the World, a Playhouse collaboration with Barbara Chandler Productions. Musical Director Christopher Leavy will accompany on the piano. These popular cabarets sell out quickly to get your tickets today!
This unique form of entertainment showcases a different professional singer each month. A truly "New York-style" cabaret, each performance is approximately 55 minutes in length with no intermission.
This production is suitable for all audiences. Age Requirements: Ages 15 & older.
| Buy tickets |