So let's see if Jeff and his team of experts can get this one. The gauntlet has been thrown down!
"Which original cast member from a well known Sondheim musical went on to become a popular Starfleet officer?"
More Broadway/Sci-Fi Trivia
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I don't know the answer, but I'm going to guess Brent Spiner.
I'm afraid that the other Jeff has faster researchers – Brent Spiner was in "Sunday in the Park with George." Although a connection can be made for non-officers Whoopi Goldberg (A Funny Thing Happened on the Way to the Forum) and Victor Garber (Sweeney Todd).
That's the actor – does anyone know the musical?
Spiner was also, post Star Trek, John Adams in a revival of 1776. That was the basis of my guessing he had been in a Broadway musical before Star Trek.
I suppose one could also assume that Spiner was one of the only series regulars with sufficient actual acting talent to have done these other things? Or perhaps that's unfair to Patrick Stewart (who was also an X-Man of course…)