The road to Ruth: Talking with playwright Rupert Holmes

It’s pretty much common knowledge that Rupert Holmes, the Tony-winning playwright whose All Things Equal: The Life and Trials of Ruth Bader Ginsburg is onstage this month at freeFall Theatre, began his career as a singer/songwriter. He is the very same Rupert Holmes whose catchy “Escape (The Piña Colada Song)” topped the pop charts in 1979.

What’s less known is that Holmes first hit the “big time” years earlier. At 21, his song “Timothy” made the Top 20, recorded by an obscure Pennsylvania group called the Buoys. In the narrative, sung over a swinging country/rock beat, the narrator describes a mine collapse in which he and two other workers – Joe and Tim – were trapped underground, slowly starving to death.

When helped arrived, Joe and the narrator were found, with full stomachs – and an unshakeable feeling that something was terribly wrong. There was no sign of Tim. “God, what did we do?” went the chorus.

“For most people,” Holmes says with mock seriousness, “writing a song about cannibalism is the launching pad for writing a play about Ruth Bader Ginsburg.”

Holmes won three Tonys for his musical The Mystery of Edwin Drood in 1986, and has had many stage successes since, including Curtains, Say Goodnight Gracie, Solitary Confinement and (with Marvin Hamlisch) The Nutty Professor. He has written two novels, as well as all 56 episodes of the TV series Remember WENN, based on one of his songs. He’ll be back on Broadway shortly with an updated version of The Pirates of Penzance.

Yet it all started with “Timothy” in 1971.

“I’m very proud of that song,” Holmes tells the Catalyst. “I know that sounds perverse. It was a case of a young man trying desperately to find a way into the music business. And trying to psych out what could get some attention.”

In other words, Holmes was aware that the record’s chances at success were slim, unless he could come up with a subject matter so distasteful that it would get banned.

“It was on the charts for something like a year, and finally got to No. 17 with a bullet. And we could never get it above that because there were certain areas of the country where they simply would not play the record.”

New York, for example, wouldn’t give “Timothy” a spin. But WLCY in Tampa/St. Petersburg put it in heavy rotation, which is why the Buoys’ followup single, “Give Up Your Guns” (also written by Holmes) includes the line “I robbed a bank in Tampa.” Holmes knew they’d automatically get airplay here.

Rupert and Babs. CBS Records.

Nevertheless, the record bombed, but Rupert Holmes had a foot in the door. In 1975, he co-produced Barbra Streisand’s Lazy Afternoon album (and contributed three songs).

La Streisand had heard Holmes’ first singer/songwriter album, Widescreen, and sought him out. She also recorded two of his songs for the movie A Star is Born.

Then came “Escape” (“If you like piña coladas/and getting caught in the rain”) and Holmes’ own star was on the rise.

“From the very beginning, I wanted to tell stories and I wanted to write music,” he says. “And I had to find a way that I could do both. When I started out in high school, I didn’t know anyone in theater – but I could play a lot of instruments, I had long hair, and telling story-songs was my way of doing theater. I wrote songs that were narratives. ‘Timothy’ has a plot. ‘Escape’ is an O. Henry story with a twist ending. There aren’t many pop songs that have twist endings.”

Legendary Broadway producer Joseph Papp and his wife were fans, and after one of Holmes’ story-song cabaret shows, Papp approached him. He said ‘You know, you’re doing theater up there; have you ever thought of writing a musical?’ I said, I’ve been thinking about it for my whole career, and I laid out the idea for The Mystery of Edwin Drood for him.”

A whimsical, musical adaptation of Charles Dickens’ unfinished final novel, Drood introduced something unique in theater: There were several possible endings; the audience voted on which would be performed.

Michelle Azar onstage in “All Things Equal.” Photo: Dalton Hamilton.

The idea for All Things Equal came from a conversation Holmes had with his frequent producing partner, Scott Stander. In March 2020, the pandemic curtain came down on theater everywhere; what, the two wondered, would they be able to tackle next, under the circumstances?

The lightbulb moment arrived: “If anything is going to get out there in this climate, a one-actor show is the way to go,” Holmes remember saying.

“People on Broadway were belting into each other’s faces, and then the entire cast would get sick. It’s always been a standard thing in theater that when somebody gets the flu, everybody in the show knows they’re all going to get the flu. It will go through an entire cast over the course of a month.”

Ginsburg, the feisty and fearless jurist appointed to the United States Supreme Court by Bill Clinton, passed away that September, at 87. She was an outspoken and beloved defender of human rights. “Outside of Queen Elizabeth,’ Holmes says, “I don’t know of anyone else that we were hanging on like: ‘Please stay alive. Please stay alive.’”

Then came lightbulb moment No. 2.

“My wife is an attorney. All my life I’ve talked about Ruth Bader Ginsburg, and her cases and her rulings, her strategies in trying to get people to understand equal rights – not just women’s rights – and I was always fascinated by the fact that she defended men to make the case in front of men that women should have equal rights. It was a great strategy, and it was really the only way around facing all those grumpy old guys in the courtrooms.

“She already had a daughter when she went to Harvard, when she was one of those nine women who were accepted. What a task, to go to Harvard, going against the grain, raising a daughter and also taking care of your husband, who’s come down with cancer. This took all the scrappiness and spirit that she could possibly have.

“And in investigating her life, her youth in Brooklyn, and her mother and her feelings about her mother, I just thought ‘This is a good time to be sharing this information, and this personality, with an audience.’

“Also, she had an interesting sense of humor. She was so dry and so droll – I thought, on a stage, I think I can bring that out. I always love it if I can get some laughs, in any kind of play, because it’s human nature to make jokes. I always say that tragedy is what we inherit as human beings, but humor is what we as a species invented to cope with that.”

All Things Equal stars Los Angeles actress Michelle Azar; she’s alone on the stage for 90 minutes. “Michelle is doing a magnificent job, I can tell that,” says Holmes, who hasn’t been able to get to St Pete – yet – to see his show with an audience. “I would watch her in rehearsals, and there’s something about her that’s very special. She’s got something.”

The show world-premiered here and will remain at freeFall through the end of the month, before moving on to New York and a 14-city tour.

RELATED READING: ‘All Things Equal’: Michelle Azar as freeFall’s RGB

Is All Things Equal Broadway bound? “Say Goodnight Gracie was the third most successful one-person show on Broadway,” Holmes says. “One-person shows can work on Broadway. I think this one could work on Broadway.

“But it’s early days; I do think we’re going to learn a lot about this show. Getting the notes from the stage manager is telling me what is working, and where we can develop it even further.”

Bay area audiences have been rapturous in their enthusiasm for Azar-as-Ginsburg; Holmes says he’s thrilled by reports that when the character announces one court victory or another, there is thunderous applause. They’re laughing at Ginsburg’s occasional pithy jokes, too.

A one-person show, “if it works well, it can feel like a one-on-one,” he believes. “It can feel like you’re having a private conversation. You’ve somehow managed to get a lunch date with Ruth Bader Ginsburg, and to talk about things in her life not through headlines and articles, but have her level with you the way people do over a cup of coffee.

“And I love that. I like that the audience has a chance to feel ‘I’m with this person, I’m learning something about them that goes beyond. I’m learning about them as a human being. And what motivates them.”

Holmes was particularly surprised to learn that Ginsburg not only loved opera, but shared an interest in it with fellow Supreme Court Justice Antonin Scalia, with whom she disagreed on just about everything else.

As a lifelong opera fan himself, Holmes was overjoyed. “That, he says, “is where I feel Ruth and I really collaborated.”

All Things Equal details and tickets are here.