Heads Up Key West – Tom Flip portraits capture locals again

Tom Flip takes Greta Holtkamp’s portrait again after five years.

Shel Silverstein wrote the lyrics, “Wanna see my smilin’ face, On the cover of the Rollin’ Stone… ” made famous when sung by Dr. Hook. Ironically, local photographer known as Tom Flip (officially Filipkowski) has taken a page from Silverstein’s songbook. As a child, Flip was inspired by Rolling Stone Magazine covers strewn on his parents’ coffee table in New Jersey. He didn’t just notice the cool portraiture Rolling Stone made famous, but realized there was a photographer behind the camera, and he wanted to be that photographer.  Getting a bachelor’s degree at The School of Visual Arts in New York and actually interning for Mark Selinger, Rolling Stone photographer, Flip learned to aim his lens at people and tell their story, not his.

Inspired by the people of Key West, Flip began the portrait series “Heads Up Key West” back in 2013, and more than 600 people showed up free of charge to have their Rolling Stone moment. So popular were the portraits that Flip is back photographing locals through September and will show the results at The Studios Of Key West Gallery October 1-14. 

“My interest isn’t water or boats or sunsets; it’s people more than anything else,” said Flip, who did his Key West artist penance photographing snorkel trips before there was even digital. He made a business out of wedding photography but recently stopped doing weddings altogether, saying, “I didn’t really go to school for that.” For now, Flip manages at Amigos Tortilla Bar and takes on projects that excite him and, obviously, the community. 

“So many things have happened to people here over the last five years, it’s fascinating to see the changes ” said Flip. This year, only about 200 people have shown up for portraits and he laments, “Maybe it’s because people can’t afford to live here any more.”

Helping with the exhibition is filmmaker Matthew Dockery, of DockLight Productions, who has been recording Flip’s conversations with the locals and recording the portrait process on video. Dockery would like to see this project get national recognition and hopes a film about Flip creating the project will work. The movie will premiere at Flip’s opening Oct.4 at the Studios of Key West.

“There is zero monetary gain; Tom and I just believe in the idea,” said Dockery.” Really it’s about and for the community.”

As Silverstsein wrote, “I ain’t kiddin’, we would make a beautiful cover, On the cover of the Rollin’ Stone.”  For more information go to TomFlip.com or Heads Up Key West on Facebook.

Portraits by Tom Flip

Hays Blinckmann
Hays Blinckmann is an oil painter, author of the novel “In The Salt,” lover of all things German including husband, children and Bundesliga. She spends her free time developing a font for sarcasm, testing foreign wines and failing miserably at home cooking.