Arts & Culture

Webb’s City: The Musical — A Nostalgic Celebration of St. Pete’s Eclectic History

todayMarch 20, 2019 12

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>> Article originally published in St. Pete Life Magazine <<

Dancing chickens? Mermaids swimming in a tank by the gift shop? Maybe you’d like a haircut and a shoe shine while having your prescriptions filled and new tires put on your car. Oh, and don’t forget the toothpaste and some socks. Sounds like the ultimate retail/entertainment fever dream, but as Dorothy would say about Oz, “It was a really truly live place”. St. Pete natives of a “certain age” have direct knowledge of this bizarre retail reality and they remember Webb’s City with fond nostalgia and the inevitable chuckle.

The brain child of medicine man turned entrepreneur, James Earl “Doc” Webb, Webb’s City became the forerunner of the megastore shopping center. Desperate to attract customers during the Great Depression, Doc Webb incorporated the popular Florida tourist attraction vibe to go along with the meat market, hardware store, beauty salon, travel agency, cafeteria, clothing store, and of course, pharmacy. And that just scratches the surface! Doc’s prevailing philosophy was, “stack it high and sell it cheap”. He was a loveable huckster, known as the “P.T. Barnum of retail”, and he was a driven man, bent on success at any cost. To attract the coveted tourist trade, beside the chickens and mermaids, there were also chimps, baseball playing ducks, zucchinis shot from cannons in the parking lot, citrus shipping, and an Arthur Murray dance studio on the roof. And it worked! At the height of its success in the 40’s, Webb City encompassed 10 city blocks with some 77 different stores and grossed $4 million dollars per year. Thousands came from near and far to see the wonder that was Webb’s City. It was known as the ‘World’s Most Unusual Drug Store” and is even credited with the invention of the “10 items or less” express lane.

But all good dreams must come to an end. With the advent of widely available shopping centers and some questionable business moves like 2 cent breakfasts and 1 dollar bills sold for 95 cents (sometimes a volume business just doesn’t quite add up), sales and crowds dwindled until, finally, the doors closed for good in 1979. But 5 decades is a pretty good run by any standard, and the legacy will live on forever.

Enter playwright, Bill Leavengood (pictured right). A St. Pete native, Leavengood is a prolific story teller and educator. Though he has been the playwrighting and theater director at Shorecrest Preparatory School for over a decade and adjunct professor at USF, Leavengood is a 2-time Eugene O’Neil Award winner with Off-Broadway success at Circle Repertory, Primary Stages, Town Hall, and The Chelsea Playhouse. His 50+ plays have also been produced around the country, and if that isn’t enough, he is a successful author, screenwriter, documentary filmmaker, and dramaturge.

In 1999, as Pinellas County was preparing to celebrate it’s centennial, Leavengood wanted to participate with a local story, produced for the stage. When his first idea of Gasparilla met with stony silence (The organizers weren’t keen on celebrating a Tampa event for a Pinellas celebration), Leavengood came up with the concept for Webb’s City. The play was a rousing success and before long, made the rounds at venues such as the Mahaffey and Ruth Eckerd Hall. With performers like Eric Davis (founder and artistic director at freeFall Theatre Company), and Roxanne Fay in early productions, “Webb’s City: The Musical” achieved such great popularity, that Leavengood and his wife decided to start a not for profit company, “Will Not Di Artists” to keep it going for future audiences.

Enter Paul Wilbourn, Executive Director of the historic Palladium Theater. Wilbourn is a Tampa native, but he was working as a journalist in LA at the time of the first “Webb’s City: The Musical” production. An accomplished musician himself, Wilbourn recounts: “When I returned to town to take over the helm at the Palladium in 2007, someone gave me a soundtrack and I was blown away. I knew that a show of this quality with a local theme was just what I was looking for.” The current upcoming production, in concert format, will be the show’s third time on the Palladium stage. “Lee Ahlin’s music is original, authentic, and just stays in your head”, says Wilbourn. Ahlin, the composer, was a co-worker of Leavengood’s at Shorecrest and is widely considered one of the best by all who have had the pleasure of performing his songs. Wilbourn says that one of his favorite songs in the show, “Wasn’t it a Good Ride”, has been requested by many friends for multiple events – even a funeral. “I’m thrilled to have “Webb’s City: The Musical” back at the Palladium.”

Enter the cast. For this interview, I had the pleasure of meeting, not only with Bill Leavengood and Paul Wilbourn, but also with Jim Sorensen (left), actor and managing director at American Stage, Cranston Cumberbatch, actor and filmmaker, and Charles Reynolds, an attorney and lifelong friend of Leavengood. Sorenson plays Doc Webb himself, conspicuously against type, as Webb was notably short and Sorenson tops 6 feet. “They had to edit all dialogue and song references that dealt with height. All the “littles” and “smalls” had to go”, Sorenson chuckled. The lone man in the room not from the Bay area, Sorenson enjoyed learning about Webb and all of his entrepreneurial shenanigans. “I was especially taken with how much Doc Webb was ultimately loved by the community, but also moved by how much his most intimate relationships suffered as a result of his ambition. He is a full, rich character that translates well in any story.”

Cranston Cumberbatch plays Leo, Webb’s lifelong friend, confidant, and advisor. The Leo character is a fictional amalgam representing the African American community of the time, but it was important to Leavengood to have the role be that of peer and friend, not subordinate. “ I am thrilled to be part of this production”, Cumberbatch says. “I remember a little about Webb’s City growing up….something about chickens”, he smiles. “But it was on its way out when I was small.” A scene near the end between Webb and Leo at the Green Benches in Williams Park is especially moving, both historically and emotionally. But, I’m a writer not a spoiler, so you’ll just have to go to the show to see it!

Charles Reynolds grew up in St. Pete with Leavengood. They were students together at Shorecrest, and though he is an attorney, not a professional actor, Reynolds loves getting to indulge his thespian pursuits for Webb’s City: The Musical. He plays the key antagonist, Frank Hubert, another character amalgam that represents a very oppositional business community. “The best part of playing Frank, is getting actual jeers and hisses from audience members leaving the theater. That’s when I feel I’ve delivered”, Reynolds laughs.

Of course, real life characters figure prominently in Doc Webb’s story. For instance, Webb’s 2 wives and his embattled son are present, clearly portraying the sometimes wrenching cost of success. Local legends Nelson Poynter Jr. and Lou Brown of the long defunct Evening Independent make appearances as well, adding to the historical authenticity of the piece. Ever loyal to his local talent resources, Leavengood uses his Shorecrest students in the cast and ensemble as well.

Everyone in the room agrees that “Webb’s City: The Musical” is a universal, yet locally inspired story, expertly told with complex characters and beautiful, Broadway quality music. It has all the history, conflict, love, loss, and laughter that you could ever possibly want in a stage show. Leavengood sums it up: “It’s five decades of the American Dream in the story of one man.”

Webb’s City: The Musical will be shown at The Palladium Theater on Friday, Saturday, and Sunday, September 21st, 22nd, and 23rd.


For ticket info:
To learn more about Bill Leavengood, visit

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Written by: #HeliumRadio

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