I spent two weeks dressing the men’s chorus in a national tour of the musical Grease. Rosie O’Donnell played Rizzo and her name was plastered all over everything. It seemed odd to me that she got top billing for a supporting character. Shouldn’t the stars of Grease be Danny and Sandy?

The show was slated to go to Broadway after it made it’s way around the country. Good Morning America came to the theater and shot a segment in Rosie’s dressing room.

“There are some amazing singers in this production of Grease. I’m not going to say that I’m one of them,” she said right into the camera. Good for her for being so candid in the interview.

Perhaps her lack of a singing voice didn’t matter, because Rosie was well on her way to stardom and would have her own hugely successful syndicated talk show not long after she made her Broadway debut.

My first face-to-face encounter with Rosie during Grease was very telling.

The only crossover to get from stage left to stage right in this theatre was to go through the basement and pass by my dressing room. Every night after “Born to Hand Jive” a parade of the cast would laugh and giggle as they ran past me. Rosie was always last, dragging herself behind. She looked a little ragged in her giant prom dress. One night she paused in my dressing room. I was the only one around.

“I am too old and too fat to be doing this,” she said to me and went on her hand-jiving way.

Rosie O’Donnell celebrated her birthday while she was in town starring in Grease. The traveling wardrobe head was dispatched to Baskin Robbins to get a couple of giant ice cream cakes for the company to celebrate. Each cake was customized with “Happy Birthday, Rosie” on it. And, of course, the folks at Baskin Robbins figured out that the cake was for the Rosie O’Donnell, star of A League of Their Own and Sleepless in Seattle.

When the head of wardrobe returned to the theatre with the cakes, there was a large envelope with a note inside one of the boxes:

“If you ever need anyone to jump into the tour give me a call.”

A young fringe theatre actress was moonlighting at Baskin Robbins (or was the ice cream girl moonlighting as an actress?) The girl included her resume and headshot with the cake. A few of my fellow dressers perused her stage credits. She had done some high school plays, but Widow Corney in a community theatre production of Oliver! was her claim to fame. Poor thing had no idea how show business really worked. The wardrobe head was kind enough to toss the envelope in the trash and not embarrass her further.

The movie version of The Flintstones had just come just out a few weeks before the Grease tour started. Rosie played Betty Rubble and was asked to present two Oscars at the Academy Awards: one for Best Animated Short Film and one for Best Live Action Short Film. The ceremony was happening while she was in town and there was a lot of backstage talk about her taking the night off from Grease to attend.

There was even more chatter about her Oscar gown. A famous designer was custom making her a dress. Rosie and the traveling wardrobe head for Grease were very nervous because the dress hadn’t found her on the tour yet. It would require a fitting backstage at the theatre and then rushed back to the designer to finish. Time was ticking.

In a huff, Rosie went to Nordstrom a few blocks away and bought a backup outfit to wear if the dress got lost. All by herself, she picked out the plainest black pantsuit that ever existed. I was asked to hem the sleeves and pants for her.

“Dear God, she’ll look like the hostess at a steak house. That dress better get here,” was all I could think while I sewed her boring backup outfit.

The designer dress never made it to town. Hopefully it would find her in Los Angeles or Rosie would be wearing PANTS to the Academy Awards.

On Oscar night, the understudy went on for Rosie O’Donnell and, for the first time, I got to hear Rizzo belt her solo to the rafters. She was sensational but I couldn’t stop thinking about Rosie O’Donnell down in Los Angeles.

There was no television backstage at Grease. This was many years before smartphones. Of course, I taped the Oscars and dashed home to watch it on my VCR after the show. I had to see what Rosie wore: did she present the Oscars in the steak house pantsuit I hemmed or the designer couture?

I sat patiently as Oscars statues were handed out one by one to Anna Paquin, Tommy Lee Jones, Jurassic Park and Schindler’s List (which sort of swept the evening).

Finally, host Whoopi Goldberg introduced Rosie.

“The star of the new Broadway production of Grease, Miss Rosie O’Donnell.”

I held my breath as Rosie made her entrance from stage left of the Dorothy Chandler Pavilion.

It’s a dress! Thank goodness! No steak house pantsuit!

The situation obviously worked out fine and Rosie O’Donnell looked amazing all dolled-up in her custom gown and jewels. I thought it was ironic that one of the two Oscars she handed out that evening was for a film called The Wrong Trousers.

Without fanfare, Rosie came back to the theatre the next night and timidly pushed through “There Are Worse Things I Can Do” seven more times before the tour left town. I missed her understudy’s rendition of the song.

Grease was nominated for Best Revival of a Musical at the Tony Awards a few months later (it didn’t win). I watched the ceremony on TV and quickly noticed that Rosie O’Donnell was suspiciously absent when the cast did their number. The dance captain filled in for Rizzo. It was probably for the best.

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 part of a series for Queen Mob's Teahouse on his experience working backstage.