Kyle Caskey

In Memory.

Kyle Caskey

Kyle Caskey has had the wonderful opportunity to take the stage of the Waterfront Playhouse in twelve productions. In 2011, he appeared in August Osage County as Little Charles. Favorite past roles include the Bellhop in Lend Me A Tenor, Mr. McQueen in Urinetown!, Juror #2 in Twelve Angry Men, Sheldon Marcus in The Best Man & Merlin Magenta in The Red Head Dilemma, an original children’s theatre production which he wrote & premiered in Chicago. He most recently performed in the world premier of Conch Republic The Musical! with the Key West Fringe Theater. He has also performed with the Studios of Key West’s One Night Stand & has six productions on his resume with The Red Barn Theatre. Prior to his arrival to Key West he was a summer stock performer with the Little Theatre-On-The Square, a repertory performer with the American Theatre Company at the Edinburgh Festival Fringe and toured for ten years with Kaleidoscope Children’s Theatre Company as a founding member. He holds a B.F.A. in Theatre Arts from Chicago’s Columbia College

 

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The latest happenings at The Waterfront Playhouse.

Announcing Waterfront Playhouse’s 86th Season

The Waterfront Playhouse, named the “Best Professional Theatre in Florida” and Florida’s oldest theatre, is proud to announce its 2024/2025 season, the 86th season in its rich history. The first show of the season, which shouldn [...]

Neil Simon’s Pulitzer Prize Winning Masterpiece to open at Key West’s Waterfront Playhouse

The award winning Waterfront Playhouse on Mallory Square has begun rehearsals for “Lost in Yonkers”- the fi [...]