Into the Woods

One of the funniest pranks I ever pulled was as the wardrobe manager for a large summer-stock season. The calendar was in rotation, meaning we flip-flopped what show we did night to night. The schedule got confusing to the cast and crew, to say the least, but it gave actors a little bit of breathing room. An actor might have a taxing, leading role in one show, and then be in the chorus of another the next night.

Just for giggles, I rolled the racks with the costumes for The King and I into the dressing rooms on a night we were doing Into the Woods. It brought sighs of relief to some actors, and panicked screams from others. One actor just put on his eyeliner and got dressed for Siam. He would have looked strange dressed that way in the woods.

Stephen Sondheim’s musical Into the Woods is one of my favorites. I was proud to be a part of this wonderful summer-stock production. Yet, solid acting, directing, and design didn’t exempt it from one of the longest and most painful onstage flubs I have ever seen in my entire career.

Act One of this musical is jolly and fun, but in Act Two, the show gets dark and deals with serious conflict between the storybook characters.

The actor who played Jack (from Jack and the Beanstalk) had shoulder length, dirty blond hair in real life. For the show, he wore a cheap Little Orphan Annie wig — short, bright red curls. He had a fetching green hat, which he wore on top of the wig.

I would pin-curl Jack’s long hair and help him into his wig cap, yet he would put his own Little Orphan Annie wig on whenever he was ready.

Near the end of the Into the Woods, there’s a very emotional scene when the Baker tells Jack that his mother has been murdered by the giant. The heart-wrenching scene between the two men was long and rather quiet.

It was the middle of the run. The Baker got bored and decided to do something new with the scene. In a moment of acting fervor, he reached up and yanked Jack’s green hat off his head, and hurled it at his chest. It was a spontaneous gesture to punctuate the seriousness of the moment.

The problem was that Jack had pinned his green hat to his Little Orphan Annie wig — rather than pinning the wig to his head. The Baker had yanked both the hat AND the wig completely off.

Stage management paged me over the intercom to the wings. I saw Jack standing center stage. He was sullen — holding the red wig and green hat in his hands. His wig cap was hanging off his head, and a couple of pin curls had come undone. Random messy strands of his real hair were sticking up all over.

The audience was silent.

The Baker’s face was purple.

The two men kept the scene going.


I asked the stage manager what she wanted me to do. We had a little bit of time at the end of the scene when Jack would exit before re-entering for his next scene. Do we put the Little Orphan Annie wig back on Jack, or do we take the pin-curls out and reveal his whole head of dirty blond hair for the end of that performance?

The stage manager paused and thought deeply. Lord knows we could have all taken a straw poll of everyone backstage and voted on it, because the scene went on and on and on with Jack standing center stage holding his bright red wig.

“Ditch the wig. But you don’t have much time to get all the pins out of his hair,” I was told.

By this point, everyone backstage was in the wings watching the farce onstage: some were laughing; others were horrified.

I gathered my other two dressers and grabbed a hairbrush. Jack finally exited the longest scene in musical theatre history. My wardrobe staff attacked his head. Hairpins were flying everywhere. People got out of our way for fear they might lose an eye. The poor actor no idea what the plan was, he just stood there as we tore at him like a piñata exploding.

Jack’s real hair had been coiled and tightly pinned up on his hot and sweaty head for over two hours. It looked like he had gotten a crazy Medusa perm. I tried to brush his hair out the best I could, but it got bigger and bigger.

“I have to go,” Jack said as he ran to his next entrance.

He entered and everyone backstage gasped. His hair was bouncing and flying all over the place –Jack and the Beanstalk in a shampoo commercial. It was priceless.

A few phone calls and meetings occured after the show.

“How did this happen?!?!?”

There was no wig department or wig person. It was just store-bought stretch wigs and everyone had to fend for themselves. Many opinions were voiced on whether or not the bright red Little Orphan Annie wig should be cut from the show for the remaining performances.

The Little Orphan Annie wig stayed in.

For the rest of the run, I personally pinned and double-checked Jack’s head. The wig and hat would cause no more drama.

We lived happily ever after.

Image of Siena College’s Into the Woods via

Dennis Milam Bensie is a writer and, for thirty years, has made his living as a dresser in professional theatre all over the United States. Short stories and poetry by Dennis have been featured in numerous publications and his essays have been seen in The Huffington Post, Boys on the Brink, and The Good Men Project. He has three books published by Coffeetown Press. This essay is the fourth in a series of essays for Queen Mob's Teahouse on his experience as a dresser.

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