Q & A

Cliff Roles Is Retiring. Sarasota's Social Scene Will Never Be the Same.

One of Sarasota's go-to photographers, Roles has decided to put down the camera after suffering a stroke earlier this year.

By Cooper Levey-Baker November 10, 2023

Cliff Roles

If you've attended a gala, a fundraiser, a soirée, a fête, a shindig, a hootenanny or any other type of big public Sarasota social function in the last decade or so, you likely know Cliff Roles.

Camera in hand, Roles has been an inescapable presence on the Sarasota circuit for years, documenting events and functions for dozens of nonprofits and organizations. On too many occasions to count, I've walked into a room and heard Roles' booming voice shout my name and then usher me into a lineup for a group shot, followed by a quick catchup about our families and careers before he was off, sprinting to take more photos.

Which is why it came as such a shock to learn earlier this year that Roles is retiring. Roles suffered a stroke while traveling in South America this summer, and has made the decision to step back from work to focus on his recovery.

Well before becoming one of Sarasota's go-to photographers, Roles led a fascinating life. He grew up in England before moving to Germany and working in the music industry promoting artists like Bon Jovi and Metallica. He first came to Sarasota in 2001 and moved here permanently a year later. In Sarasota, he threw himself into acting and radio work and even did a stint as a circus ringmaster before launching his career behind the camera. In addition to shooting so many Sarasota scenes and events, he has taken headshots and portraits and has traveled the world creating images that he later published in books and shared with his many friends and followers on Facebook.

The stroke has affected Roles' speech, but through his friend Renee Phinney, we were recently able to catch up with him to learn more about his decision to put down the camera.

How are you feeling?

"I'm slowly improving with the help of my wife and a lot of therapy."

Can you describe your condition?

"The stroke happened on my left side, which affected my speech and the use of my right leg and arm. I'm gradually able to say full sentences and I'm walking much better. There's still weakness in my right leg, and, being right-handed, I have to relearn how to write and text. But with time and effort I'm hopeful for a full recovery."

Are you planning to stay in the Sarasota area?

"My wife and I have not made that decision yet. I have a lot of recovering to do. We are considering a couple options, but our granddaughters have moved away from this area and we are considering following them."

You've had such a long and varied career. Music, radio, photography—was there one aspect of your career that you enjoyed more than others?

"I enjoyed everything that I became involved in. It's hard to pick one aspect. One area that stands out, since it was fun and challenging, was my acting. I had so much fun being on stage. Another was my two years as ringmaster of Circus Sarasota. But photography gave me the freedom to not only earn a living, but to also be a part of the many productions and social events in Sarasota."

You've been such an integral part of Sarasota's social scene for so many years. Do any special memories stand out?

"The people I met will always be the standout memories. Without them and the friendships I made along the way, taking pictures would be boring. The interaction and conversations with everyone involved with the events, from the working staff to all the guests who participated, made it all worthwhile."

Your annual photography trips became somewhat of a ritual for you and your Facebook friends. Do you have any favorite trips or destinations?

"My three-month trip to Australia and New Zealand, I have to admit, was the most exciting. From sleeping in a tent in the middle of the desert to holding a kangaroo or watching the actions of a bearded dragon in the wild—I would return again in a heartbeat. The second standout would be my experience traveling to Antarctica."

Is there anything friends or fans can do to support you?

"I hope friends and fans will continue to enjoy looking at all the photos I've taken of them, in addition to the photos from my 'walkabouts.' They can all be viewed at cliffroles.smugmug.com, and shortly a calendar for 2024 will be available for purchase. I hope they will have fond memories of me and our conversations at the events I've photographed. I thank everyone for all the cards, flowers, gifts and warm thoughts and prayers. It has meant a lot and has helped me keep the faith during this recovery."

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