Meet Freddy Stebbins: Miami's Homegrown Comic Who Nails Our Weird Cultural Mashup Perfectly

‍Freddy Stebbins, born and raised in Miami, is an easygoing guy. But try talking to him when he’s on a roll—it’s nearly impossible to keep a straight face or dry eyes. When this stand-up comedic genius starts improvising, belly laughs erupt, endorphins surge, and conversation just... pauses while everyone catches their breath.

Off stage, Stebbins is quiet, subdued, maybe even a little shy. In person, he’s a great conversationalist—genuine, warm-hearted, the real deal. But when he hits the spotlight, he becomes a perfect Miami anomaly: deadpan American one minute, deliciously Cuban the next. He barely speaks Spanish, yet he parodies every stereotype our Magic City has produced over the last century—and then some.

In character, Stebbins dishes out accents, mannerisms, and turns of phrase like the best steaming plate of fried plantains east of the Palmetto. If you’ve got a love/hate thing with Miami, he’s your guy. He’s onto you—and you’re laughing harder because you’re laughing with him.

From Scholar to Stage (and Back Again)

Stebbins wasn’t always chasing laughs. He enrolled at the University of Miami, became a politically active campus leader, earned Iron Arrow induction (UM’s highest honor) his senior year, and later completed a Master’s in Humanities. Today he’s still in academia, teaching Social Science at Miami Dade College’s Wolfson Campus. His classes fill up fast—students snap them up the moment enrollment opens.

No surprise there. Someone who slips into characters so effortlessly makes for an entertaining professor. He teaches a Social Environment course, including World History. “You should see me do Napoleon in class,” he said, tucking his right palm into his button-down shirt. “I’m the nutty professor.”

History runs in the family (sort of). Dr. Paul George, Miami’s foremost historian and tour guide, isn’t blood-related, but Stebbins calls him “uncle” because the Georges and Stebbins families have been close for generations—both deeply rooted in old Miami. Stebbins occasionally subs for Dr. G’s Little Havana tours. “I’m very passionate about the city,” he said. “I want people to understand Miami for the complex and colorful place it is. Being a true Miamian is a unique experience. I want to share that.”

His roots go way back—“B.C.,” as his character Freddy Stebbinowitz would say: Before Cubans. His father’s side traces to Miami-Dade pioneering stock—sturdy, plain-speaking folk. His mother is Colombian. That cultural collision produced a kid who “got” Miami early and loved it despite (or because of) its quirks.

“I was around when my American grandmother still called Miami ‘My-am-uh’ in a Southern accent,” Stebbins recalled. “I’d go home to a Southern household in southwest Miami after spending the day with Cuban friends at school.”

Most forget Miami was once a sleepy Southern backwater before the Caribbean and Latin American waves arrived. For Stebbins, family life could’ve been a 1940s Georgia postcard—until the Cubans changed everything overnight. He relates to the bicultural experience many of his forty-something, second-generation Cuban-American friends had, but with a gringo twist.

“We’d eat arroz con pollo and flan at the dinner table,” he continued, “but I’d have no choice but to hear bitter Anglo stories about the Cubans—even though I had Cuban buddies.”

That mix of accents, cultures, and home-vs-school tension fueled his comedy for years. His characters range from a hunchbacked, hilarious curmudgeon Jewish landlord (Freddy Stebbinowitz) to a buxom, bossy Cuban grandmother (Frederika)—all sharp social commentary on the wild variety that makes Miami Miami.

Stebbins is a living sponge, soaking up everything around him. Hints of his talent showed early. The awkward teen at Christopher Columbus High School discovered making people laugh helped navigate adolescence. “Cubans found me hysterical,” he said. “By 15, I knew I was really good at accents.”

Influences and Characters

He trained in Los Angeles with The Groundlings (one of the country’s top improv troupes) for five years, did radio with the LA Dodgers, and a full season on the Travel Channel’s Get Packing. But Miami always called him home. “My talent reflects the unique faces of Miami,” he said. “There are so many nuances. Personalities here aren’t just accents—they’re points of view.”

He knows why passion runs so hot here: “It’s raw. Old Southerners lived here, then overnight Spanish-speaking people came. My dad was a real gringo; my mom was Colombian. There was always conflict, tension at the dinner table. I was always caught in the middle.”

Growing up in Miami was a riot—but not always funny. “People up north have snow days,” he quipped. “In the 80s, we had riot days.”

He lived through the Mariel boatlift and Tent City—just 100 yards from his great-grandfather’s house on the Miami River (the first optometrist on the riverbank). Absorbing the city’s rich, controversial history, he built a pantheon of characters: Aunt Weezie (old Georgia cracker, based on his real great-aunt—“the last American to leave Miami,” he laughed, “taking her stars-and-stripes flag with her”); a bubbly young Latina FIU student with a quasi-Valley-girl accent (“too young to realize she loves Miami... materialistic, but you still have to love her”).

The 1970s sitcom Que Pasa, USA? was huge for him—especially Velia Martinez’s Cuban grandmother. “I loved the exaggeration, tackiness, cheesiness, flamboyance, even arrogance,” he said. “The color and confusion attracted me. It was a weird, freakin’ fruitcake. This fruitcake is still what we call Miami.”

Freddy Stebbins Today (2026 update)

Freddy’s still very much Miami’s homegrown comedic treasure. He continues teaching Social Sciences at Miami Dade College (his classes remain popular and fill quickly), while staying active in comedy—stand-up, improv, and character work. He’s also become a go-to Miami historian and tour guide through FreddyMiamiTours.com, leading engaging, insightful tours of South Florida/Miami that blend humor, history, and local insight.

Recent years have seen him hosting events, MCing parades, filming short films and TV pilots, performing at spots like Wynwood and Coral Gables, and staying connected with the community (including family traditions like the Turkey Bowl and collaborations with friends).

His social media (@freddystebbins on X and Instagram) is full of updates on shows, tours, and Miami life—still capturing the city’s quirks with the same sharp, affectionate eye.

Freddy’s passion for Miami hasn’t faded—he’s just expanded the ways he shares it. Catch him live when you can; the laughs (and the love for this “weird, freakin’ fruitcake” of a city) are as fresh as ever.

Editor’s Note: Originally published November 28, 2009, this article has been lightly polished for readability while preserving Maria de los Angeles' first-hand perspective on living in Miami.