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| | Gigolo
The New Cole Porter Revue
March 14 - April 12, 2025
Previews: Mar. 13 at 7:30pm & Mar. 14 at 2:00pm
Music and Lyrics by Cole Porter
Conceived by Paul Gilger
An audience favorite from the Playhouse's 1st Annual Florida Festival of New Musicals! Inspired by the life of Porfirio Rubirosa, Gigolo uses a collection of iconic Cole Porter songs to tell the tale of a jet-setting, international playboy and his relationships with four beautiful women. The outstanding score features 25 Cole Porter classics including "You're the Top," "Let's Do It," "Why Can't You Behave," "I've Got You Under My Skin" and more!
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 - VIRTUAL
VIRTUAL DATES: April 11-14, 2025
Local Treasure Kevin Kelly debuts his latest cabaret, I've Heard That Song Before, 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 Mr. Kelly 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 Russell Stephens - LIVE
LIVE DATES:
April 23 & 24, 2025 @ 7:30pm
Playhouse veteran Russell Stephens debuts his latest cabaret in The Winter Park Playhouse Spotlight Cabaret Series. Join Russell for an entertaining evening of story and song!
Playhouse Patrons will remember Mr. Stephens from his Playhouse cabarets and Mainstage performances including Sh-Boom!, Christmas My Way, Crazy for Gershwin and A Swingin' Christmas! 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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| | Route 66
May 9 - 18 & May 29 - June 8, 2025
Previews: May 8 at 7:30pm & May 9 at 2:00pm
Written & Created by Roger Bean / Musical Arrangements by Brian Baker
Jump in the car and enjoy a high-octane musical celebration along the iconic ROUTE 66! Beginning with the sounds of 1950s Chicago and traveling along the "Main Street of America" to the California coast with surf music of the 1960's, this exciting musical revue features four men singing 34 of the greatest "Rock 'n' Road" hits of the 20th century. Songs include "Dead Man's Curve," "King of the Road," " Little Old Lady from Pasadena," "Beep Beep," "Little GTO," "Fun, Fun, Fun," and many more. Get your kicks with this smash coast-to-coast hit musical!
This production is suitable for all audiences. Age Requirements: Ages 15 & older.
NO LATE SEATING.
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| | Spotlight Cabaret Series
featuring Russell Stephens - VIRTUAL
VIRTUAL DATES: May 9-12, 2025
Playhouse veteran Russell Stephens debuts his latest cabaret in The Winter Park Playhouse Spotlight Cabaret Series. Join Russell for an entertaining evening of story and song!
Playhouse Patrons will remember Mr. Stephens from his Playhouse cabarets and Mainstage performances including Sh-Boom!, Christmas My Way, Crazy for Gershwin and A Swingin' Christmas! 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 Desiree Montes - LIVE
LIVE DATES:
May 28 & 29, 2025 @ 7:30pm
Superb vocalist Desiree Montes debuts her latest cabaret in The Winter Park Playhouse Spotlight Cabaret Series. Join Desiree for an entertaining evening of story and song!
Playhouse Patrons will remember Ms. Montes from her performances in the Florida Festival of New Musicals. 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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| | Sounds of the World Series: Spirituals, Jazz & Opera
Honoring Black Music Appreciation History Month
LIVE DATE:
Thursday, June 12, 2025 @ 7:30pm
In honor of Black Music Appreciation Month, The Winter Park Playhouse has teamed up with Barbara Chandler Productions to present Spirituals, Jazz & Opera, an evening celebrating black music featuring Mark Wright-Ahern. This unique one night event will take place in our beautiful lobby bar/cabaret space.
Mark Wright-Ahern will delight audiences with an evening of Spirituals, Pop, Broadway & Opera as he pays tribute to the legendary black music and musicians. These popular events sell out quickly so get your tickets today!
The performance is approximately 55 minutes in length with no intermission. Doors open at 6:30pm for general seating.
This production is suitable for all audiences. Age Requirements: Ages 15 & older.
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| | Spotlight Cabaret Series
featuring Desiree Montes - VIRTUAL
VIRTUAL DATES: June 13-16, 2025
Superb vocalist Desiree Montes debuts her latest cabaret in The Winter Park Playhouse Spotlight Cabaret Series. Join Desiree for an entertaining evening of story and song!
Playhouse Patrons will remember Ms. Montes from her performances in the Florida Festival of New Musicals. 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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