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How to Succeed in Business Without Really Trying at The Press Box Theater
Dates: 5/15/2026 - 5/24/2026
📍 Theatre: The Press Box Theater
55 Heritage Road
Southbury, CT
Tickets: $30-$45
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Winner of seven Tony Awards, including Best Musical, How to Succeed is one of the sharpest and most beloved comedies ever written for the stage — a gleeful satire of corporate ambition, office politics, and the fine art of getting ahead.
Directed by Carol Ziske, who co-starred alongside Tony winner Robert Morse in a production he both directed and starred in — bringing a rare, firsthand connection to one of musical theatre's most iconic roles.
Cast and Creative Team for How to Succeed in Business Without Really Trying at The Press Box Theater
Cast
Ben Goffredo
J. Pierrepont Finch
Lucrezia Zichichi
Rosemary Pilkington
Tyler Caisse
Bud Frump
Bob Filipowich
J. B. Biggley
Katherine Griffin
Smitty
Kadie Toderland
Hedy LaRue
Patti Rice
Miss Jones
Chris Guertin
Bert Bratt
Tyler Panek
Mr. Twimble
Charley Borden
Wally Womper
Douglas Schlicher
Book Voice
Katie Seppa
Ms. Krumholz/Ensemble
Steven Taliaferro
Gatch/Ensemble
Jon Ross
Ovington/Ensemble
Donovan Shaw
Ensemble
Griffin O'Neil
Ensemble
Sierra Magnavice
Ensemble
Creative Team
Carol Ziske
Director
William Linster
Music Director
Debra Cryan
Stage Manager
Chris Guertin
Set Construction
Choreography
Matthew Benson
Choreography
Katherine Griffin
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The Press Box Theater Frequently Asked QuestionsFAQ
Where is The Press Box Theater located?
The Press Box Theater is at 55 Heritage Road, Southbury, CT.
What shows have played recently at The Press Box Theater?
What shows are coming up next at The Press Box Theater?
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