
Stephen Sondheim fans, if they know the name Charles Gilbert, know it as the name of the fellow who wrote an unsuccessful play that gave Sondheim the germ of an idea that led to him and John Weidman developing the musical Assassins. And while that is correct as far as it goes, Charlie Gilbert has done far more than simply writing one unsuccessful play.
The way that came about is this. In 1977 Charlie Gilbert began to write a musical about men and women who tried to assassinate American presidents. It was produced by the Theatre Express in Pittsburgh, PA, in 1979. He also submitted the script to Stuart Ostrow’s Musical Theater Lab, which is where Sondheim happened to see it.
In 1988 Gilbert received a letter from Sondheim
writing to ask if you would object to my exploring the basic idea on my own or possibly with a collaborator.
I don’t know whether or not in the intervening years you decided to go back to the notion and redevelop it or to abandon it. Obviously, the idea of a show about assassins is not what the lawyers would call protectable, but I wouldn’t want to interfere in any way with any plans you might have for it. If, however, it has been indeed consigned to your creative attic, I would greatly appreciate your letting me know. As a matter of curiosity, I would also like to read your script once again, if you could spare a copy.
Gilbert and Sondheim did, of course, reach a legal agreement, and what resulted from that was the 1990 Sondheim/Weidman musical Assassins.
Which Charlie Gilbert went to see. He probably had complimentary house seats, I’m guessing.

By that time Gilbert was on the faculty of Philadelphia’s University of the Arts, and he was directing at least one musical with its students each year, very often a Sondheim musical.
Such as Into the Woods. I think that was the first show that he directed that I saw. He added a framing device that I didn’t think added anything helpful, but other than that, his student cast acquitted themselves wonderfully. By the time I saw it, I had already seen the show many times, so I knew it quite well, and I was impressed by some very different interpretations given by some of the cast members, and some of the lines which had always been played for laughs were now given more poignant readings.
Then in 1994 Charlie directed the Philadelphia premiere of the Sondheim/Weidman version of Assassins for the Philadelphia Area Repertory Theatre. He cast some of his former students as well as his wife D’Arcy Webb in some of the roles, and frankly I don’t expect to see a better production of that show—ever.

Other Sondheim shows that he directed and that I saw at the University of the Arts were Company and Sunday in the Park with George, both very well done.
Then in 1998 he exercised a different talent by playing keyboards in the orchestra of the Arden Theatre’s production of Sondheim and Furth’s Merrily We Roll Along. That was a terrific production, one of Arden’s best ever.
During that time period, I was active on a Sondheim mailing list, and Charlie Gilbert would drop in from time to time. I also exchanged a few private emails with Charlie. Alas, I no longer have those emails because I was with a different ISP at the time, and a different email address, etc. Although through the years I’ve tried to preserve those emails, somewhere along the line they were lost.

But I do recall a couple things that Charlie mentioned about that Merrily production. It featured Jilline Ringle, who had played Emma Goldman in Charlie’s production of Assassins, in the role of Mary—a role that she was born to play, according to Charlie.
Also, he wrote a fairly lengthy email comparing the Overture of Merrily to that of Gypsy, pointing out lots of musical similarities. I truly wish I still had that message.
Anyway, he’s done lots more in musical theater, not just the things that I’ve seen. And he has his own web site chasgilbert.com where he has more information.
And he’s aged a bit since that 1990 picture was taken.

Now after all that I truly wish I had a video of his powerful 1994 production of Assassins to offer you, but I don’t. So I’ll have to settle for this reasonably good version of “The Gun Song”.