Libby Dean Lee: She’s in for the laughs



Libby Dean Lee grew up in Barrington, Rhode Island, and came to Key West 32 years ago because “it is the perfect place to live.” For the most part, Libby has led a fairly uncomplicated life in paradise and dedicating herself to only one job at the infamous easy breezy outdoor tiki bar overlooking where the gulf meets the Atlantic at Ocean Key Resort, since moving to the island. Now do the math. That means she has been working there for 32 years, which is pretty impressive regardless of what profession you are in. She has seen the luxury vacation destination go through decades of transformation, first as a bartender in the lobby where the gift shop now is, and then with Billyfish Bar & Grill before it officially became Sunset Pier which is what it is known as to this day.

“It was weird,” Libby says jokingly when remembering the history of the building. As you’ll come to find out, Libby is full of dry humor and a witty sarcasm that keep her customers happily engaged the whole time they are at the bar. She’s kind of known for it, somehow always gets away with it and it is kind of what gives her a part of her charm. There are not a lot of people who can do that and manage to avoid getting into trouble. She knows how to dish out just the right amount, at just the right time without crossing the line. In fact, people love her for it.

“I like everything about bartending. I even enjoy the idiots” she chuckles. “I’m always in it for the laughs.”

A customer catches on to her slight cheekiness and says, “I like this lady,” and then proceeds to join in on the fun. They go back and forth while he orders his girlfriend a drink in a carved coconut shell souvenir cup and the couple end up leaving with big smiles on their faces. Her character seems to be contagious.

But lately thing’s haven’t been as uncomplicated as they might look for Libby out on the easy breezy pier. Libby lives on Big Pine Key in one of the areas hit the worst by Category 4 Hurricane Irma. It happened so recently, that it is still a major topic of conversation up and down the Florida Keys. Even visitors from far away stop by to hear her side of the story, but not all are ready for what she has to say. After all, she is still a victim living in the aftermath of the storm. On top of that, the 120-foot pier itself was so badly damaged that is has been closed for remodeling, resulting in a loss of business.

When Libby returned from the mandatory evacuation, she found her home flooded with 2 feet of water that had ruined almost all of her furniture and put the structure itself in a jeopardy. Although they have been able to get their gas stove going again so that they don’t have to exclusively use the barbecue anymore, and have an outdoor shower that is very refreshing except when the temperature drops down to the low 70s and then refreshing becomes freezing, Libby and her boyfriend are still waiting for FEMA to give them some sort of answer that is positive among many scenarios that each have their own problems.

“We had to tear everything up,” Libby explains, “we don’t yet know if we are going to have to demolish the house, sell the property, or if we have to rebuild.”

All of this occurring just when she was about to retire so that she could focus on some of her favorite things like reading a book, going to the beach, taking professional quality nature-inspired photos that you can view on her Facebook page Sunrise of the Florida Keys, or “staying away from people.”

Again, the customers smile along with her as she tells me this.

Then suddenly, Libby decides to direct her harmless banter at me when I ask her how she would describe her bartending style.

“How would you describe me?” she quips to the amusement of her small fan club. I can tell that these are regulars who go to see her almost every day and who have become her friends.

Besides Sunset Pier, Libby has only had one other bartending job back in Providence at a place called Last Call Saloon that she compares to being a lot like Sloppy Joe’s. She started bartending because it seemed like an easy way to go out and socialize, and it has now become a big part of what defines who she is. Libby spends half of her week at Sunset Pier every Friday through Monday from 11 a.m. until about 4 p.m. or later depending on what time of the year you are there and when the sun goes down. Not only does Sunset Pier serve a full menu for lunch and dinner, but it is also one of the best spots on the island to enjoy the daily sunset celebration as it is situated adjacent to Mallory Square and directly across from an open horizon.

I think I’ve given everyone an idea of what you might encounter if you go to see Libby for one of her famous piña coladas on the rocks or fresh lemonade cocktails with muddled lemon and simple syrup. She’s probably gonna make you giggle a little, she might even make fun of you, but she’s also really exceptional at making people feel comfortable. She’s a really good listener and is willing to give discerning advice even if she is going through something terrible as well. I guess you could say that Libby just has a natural knack for finding the right words to fit into any moment. There is absolutely nothing phony about her bartending; it’s just her being herself and enjoying what she does.

“Sunset Pier is a great place to be on the ocean, with amazing food, really, really good drinks, and good people watching.” ¦

Sunset Pier @ Ocean Key Resort 0 Duval Street

8 responses to “BARTENDER OF THE WEEK”

  1. Libby says:

    Thanks Jen!

  2. Eva Grace says:

    i Know Libby from her Last Call bartending days. She was always fun to hang out with and a great person.

  3. Steve & Linda from Cincinnati says:

    My wife and I are in Key West every May. The first bar we hit is Sunset Pier and hope Libby is behind the bar. It’s always good to see a friend that treats you like a local. Libby, see you on May 12!

  4. Emerson Torrey says:

    I grew up with Libby. She has always had a knack for putting people in there place using just a few words. But as her boyfriend Greg (also and old friend) could tell you she doesn’t need words to put you in your place. Just a look. Certainly one of my favorite people on the planet!!

  5. Mark Love says:

    I worked with Libby directly and indirectly at The SSP for 12 years. I don’t think I have fonder memories of a nicer person than Libby.

  6. Elizabeth Sonaglia says:

    Very well written article. It translates exactly who Libby is. That dry sense of humor is definitely her trademark. My favorite person at the Sunset Pier. Wishing life becomes uncomplicated for her again soon.

  7. Scott says:

    Nice to hear good things about friends from my home town.Know you guys will come back stronger.

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