Gala Season Magic: Journey Through the Lens of Sarasota’s Celebrated Photographer, Cliff Roles

By Kaileia Suvannamaccha | November 2023 | Photos by Cliff Roles

In the heart of Sarasota’s vibrant arts and philanthropic scene, one name shines bright—Cliff Roles. A celebrated photographer, Cliff has dedicated his lens to immortalizing the glamour and elegance of Sarasota’s most prestigious events during the city’s annual “gala season.” While Cliff’s work is widely recognized in Sarasota, few may be aware of the extensive and diverse background that led him to become the iconic photographer he is today.

A Remarkable Journey

Before his photography career, Cliff Roles led a diverse and dynamic life. Originally from Croydon, England, he ventured into the world of sales and promotions. This journey led him to work with some of the biggest names in the music industry and witness pivotal moments in history, one of the most memorable of which was watching the fall of the Berlin Wall in 1989. In 1984, he charmed his way into a music-publishing company in Germany, where he worked in marketing and promotions for over 130 of the world’s most renowned rock and pop stars of the 80s and 90s, including Elton John, Celine Dion, Bon Jovi, Def Leppard, and Kiss, to name a few.

A Transition to Sarasota

The turn of the millennium marked a change in career path for Cliff. He became a professional German/English translator, an opportunity that gave him the flexibility to work from anywhere in the world. Captivated by the beauty of Florida, Cliff flirted with the idea of moving to the sunshine state before finally planting his roots in Sarasota after meeting his wife, Maria. 

Beyond the Lens

While Cliff is most often celebrated for his work behind the camera, he has also worn different hats in the world of entertainment and marketing. His commitment to putting the subject ahead of himself highlights his dedication to his craft.

In 2003, he discovered his love for acting, performing in various productions that showcased his versatility from the Asolo Repertory Theatre, Players of Sarasota, and Venice Theatre to the Manatee Players, Golden Apple Dinner Theatre, and the Backlot. Not only was he passionate, but also incredibly talented, recognized by nearly every local media publication and was awarded “Best Local Actor” two years in a row, and voted “Best Local Charismatic Actor,” among many other notable titles over the years. He was even asked to be Ringmaster of Circus Sarasota in 2006 and 2007.

Having an impressive ability to excel at anything creative he put his mind to, Cliff went on to host his very own talkshow that aired on WIBQ radio called “Talk Of The Sun Coast.” He also broadcasted through Sarasota’s Community Radio WSLR and local AM station WSRQ and was voted “Best Local Media Personality.”

Gala Season Extravaganza

Cliff’s journey into photography was serendipitous. It all began in 2007. At the time, he was emceeing a large number of non-profit events in Sarasota when he was asked to take pictures of a few attendees for their Black Tie pages. He had an obvious natural talent, and it led him to become the community’s premier event photographer, voted “Best Photographer” two years in a row. He has been heavily sought out and booked throughout Sarasota’s social season, lasting October through May ever since. 

As the city’s most highly anticipated fundraising events grew more extravagant year by year, Cliff was there to capture the magical moments that would have otherwise gone unseen. These galas, including The Orchid Ball, Sarasota Memorial Foundation, The Asolo, The Circus Sarasota, and Ringling College’s annual Avant Garde, have been his canvas, creating timeless memories. Reflecting on this time of year, he says, “I got to know the world’s best people, and I enjoyed getting involved in charities, especially children’s charities.”

Capturing Souls at Their Best

A down-to-earth and sociable individual, Cliff dedicated his life to capturing people at their best during these extravagant galas. 

“Amongst the countless events I’ve photographed through the years, I have a warm spot for the Asolo Repertory Theater, all the wonderful production events I was able to photograph, and the wonderful friendships with all the artists I was able to obtain,” he says. 

What makes his approach really standout is the emphasis he places on his role of ensuring that his subjects stand to their advantage, not his. He adds, “You must put the subject over yourself. You should know everything about the organization you’re going to photograph. You have to know their needs and passions to really understand what needs to be photographed.”

One of Cliff’s lifelong passions has been travel. In 2013, Cliff published his book, Walkabout Europe, based on his visit to 15 countries in 50 days with a backpack and his camera. Every summer, between June and September, he likes to “go walkabout” and discover new places across the globe. It has been an exciting way for him to expand his mind, and his portfolio.

Once the pandemic hit, Cliff offered “Coronicals,” short “drive-by” photo sessions at low cost that depicted how people were living during this time. At some point in the near future, he plans to publish a coffee-table book, “Cliff Roles’ Coronicals,” that will feature photos from this era. 

A Screeching Halt and a New Beginning

Cliff has reached a significant turning point in his life, a stroke that has unfortunately caused his life and career to come to a screeching halt. His physical therapy has been extensive, but slowly and surely, he is on his way to recovery.

While Cliff’s heart and soul are firmly anchored in Sarasota, he intends to spend more time with his grandchildren as he moves into his retirement years.

A Passion Beyond Profit

Throughout his journey, one thing remains clear – photography isn’t merely a means to make a living; it’s a means to make a difference. For Cliff, it’s about capturing the moments that matter, highlighting the organizations that shape Sarasota, and preserving the legacies of those who contribute to the community.

As Cliff Roles reflects on his life and career, it’s evident that he has not just been a witness to Sarasota’s transformation; he’s been an active participant in creating and quite literally framing the Sarasota we know and love today. His dedication to photography, his commitment to preserving memories, and his sociable nature have made him an icon in Sarasota’s vibrant arts and culture scene. Cliff Roles is more than a photographer. He’s an artist and a storyteller—a true Sarasota legend.

To view more of Cliff’s work, please visit his portfolio at www.cliffroles.smugmug.com.