Experience Key West Like a Local with Cabaret Superstar Randy Roberts

Whether it’s the tropical climate, the welcoming atmosphere, or its independent spirit, Key West has long been a haven for artists, performers and creatives. It’s not uncommon to spend an evening sharing drinks with an author, a painter or even Cher.

Okay, it might not be the actual Queen of Comebacks, but, if you’re lucky, you might find yourself belly up to the bar beside Key West’s cabaret superstar, Randy Roberts.


A master entertainer, Roberts has been delighting crowds with his performances as Cher, Bette Midler and more for decades. A trip to the Conch Republic simply isn’t complete without a stop at LaTeDa to see his Crystal Room Cabaret, but you may also have seen him perform on America’s Got Talent, the Vegas strip, or on ABC’s One Life to Live.

Of course, when you’re looking for the best, you always consult a queen. So, we chatted with Roberts about his favorite Key West spots and what makes performing on the island so special.

You’ve been performing for more than 30 years. How did you discover cabaret was your calling?

I don’t know that I discovered it necessarily. I started doing drag in the bars of Norfolk, Virginia, lip-syncing. At that time, people were at tables watching the show, it wasn’t standing around in a disco. Then I worked on harbor cruise ships where people were seated, so I was used to a captive audience. That’s what cabaret gives you as well, instead of a disco, where people just hand you a bunch of dollars, and you’re running around. I like a captive audience that’s not going anywhere, and they’re there to see what I’m doing. I’m theatrically trained, so that’s my goal. I have a beginning, middle, end, and in-between it’s very flexible. I like them to go for the ride, but I like to be the conductor!

As someone who’s performed all over the place, what’s unique about performing in Key West?

Key West is a tiny island where it’s summer ten months of the year, maybe even 11. And everybody comes here to get away. You have a captive audience. The whole island is two miles by four miles, and they’re all here to have a good time. If that’s what you offer them, you’re in the right place at the right time with the right product. I got lucky. Everyone loves to come here. Also, all [are] welcome. It used to be this was a gay destination, because everybody felt safe. Then everybody found out it was safe, and everybody came here! Isn’t that the way it is with all the gay destinations? If I see one more stroller with a dog in it and a kid on a leash…

You’re known for these impersonations, like Cher and Bette Midler. How do you choose your divas?

It’s a combination of things. Usually, it’s got to be either a really strong look-alike or look-enough-like and sound-enough-like. It’s illusion. You’ve got to give them enough that they believe what they’re seeing. I’m not a carbon copy. I’m not an illusionist who becomes the person, because I always kind of come through my characters … not “caricatures.” It’s not that. I don’t necessarily make fun of them, or, as the British says, “take the piss out of them.” You have to do a little more.

It’s a loving homage.

That’s a nice way to put it. And always in the best of taste — borderline, in the best of taste.

What surprised you most about your experience in Key West?

Acceptance across the board. Going to dinner at somebody’s house, and on your right is the CEO of some huge corporation, and on your left is the busboy from one of the restaurants, across the table is a retired millionaire and next to them is the waitress from Denny’s — everyone’s at the table, and there’s no judgment.

It’s funny you say that, because I’ve heard a very similar sentiment from lots of other people in Key West.

That’s why the motto is “One human family.”

Where in the city do you recharge?

I like restaurants. I like to go to Nine One Five and sit at the bar. I know the bartender there. After my show, I grab a drink and a bite there. They’ve got a second restaurant upstairs called Point5. I’ve been going there since they opened, it’s been, I think, 15 years now.

What’s your favorite dish or signature cocktail?

I like their ceviche. I’ve never had anything like it. It’s fresh and light and really good. And the fried calamari. They have the best french fries probably in Key West. Not that I eat carbs! Upstairs at Point5 they have a pistachio-walnut taco served on romaine. It’s unbelievable, you’d never know it was nuts. Another place I like to go is this little, tucked-away place called The Roost. It’s on Fleming. It’s a beautiful bar with two small tables or three small tables. It’s a liquor store, but a high-end liquor store. They have a happy hour with half-price caviar, and half-price smoked salmon and homemade deviled eggs and $10 martinis. So, it’s a little upscale, but you can still go in there in t-shirts and a tanktop.

Which is very Key West!

The Little Room Jazz Club is good for music at night. LaTeDa for tea dance on Sunday. If you want to get a little sun and good cocktails and fresh air, go to Louie’s Backyard deck. The backyard is the Atlantic Ocean. Go there for lunch or happy hour. If you go there for dinner, and it’s dark, you don’t see the ocean.

Besides seeing your show, of course, what’s the ONE thing everyone visiting Key West should do?

Go to the Butterfly Conservatory. It sounds hokey, but you walk in there, and you exhale. There’s butterflies, there’s quail running at your feet. If you’re there at the right time, they have two flamingos, Rhett and Scarlett, that they let out of their pen to run all over the place. If you’re there at the right time, they tell you to sit down on a bench, and the flamingos will come over and tussle your hair with their beaks. It’s bizarre! … You can also see great theater here. We get national tours. Kristen Chenoweth is coming to perform again, Sutton Foster is coming down to perform. I’m doing a show with Faith Prince in February, we’re doing a show together.

What’s a real authentic spot, where travelers can connect with the community?

There’s a place called Bobby’s Monkey Bar. Everybody goes there. You know if you go there, you don’t get out before 3:30. You stink of cigarette smoke, and you’ve sung bad karaoke, you feel like sh*t the next day. That’s really old Key West. And it’s gay-owned and operated, except for Elaine, ya gotta love her … Everyone should experience Bobby’s Monkey Bar … It’s a real old-fashioned Key West joint. Play pool, play darts, sing karaoke, have too much to drink, reek of cigarette smoke, see all your friends, stumble out at four in the morning — so I’ve heard!

What’s something you want people to know before they visit for the first time?

All are welcome here, as long as you welcome all.

Published at Thu, 14 Nov 2019 17:31:17 +0000