Top 25 SOBEWFF Moments of the Past 25 Years

For 25 years, the South Beach Wine & Food Festival (SOBEWFF) has been defined by unforgettable moments, but no one has seen it all quite like founder and director Lee Schrager. In an exclusive interview with New Times, Schrager pulls back the curtain on the highs, the history, and the absolute chaos that helped shape one of the world’s most iconic food festivals. From Willie Nelson casually performing on the sand to Mario Batali going completely off the rails at a royal tribute dinner, these stories are as legendary as they are unbelievable.

As SOBEWFF gears up for its 25th year (February 19-22), Schrager reflects on the 25 moments that made the festival what it is today, the magical, the monumental, and the moments where everything almost went sideways. There are jaw-dropping celebrity appearances, behind-the-scenes mishaps, weather disasters, no-shows, and wild nights that prove this festival has always been about more than just food. Trust me, some of these stories are so outrageous you’ll wonder how they haven’t been told sooner. Buckle up, you’re going to want to read every single one.

1. Willie Nelson Takes the Stage at Bubble Q (2004)

One of the most legendary nights in festival history came early on, when Willie Nelson took the stage at the Bubble Q, an evening barbecue set right on the sand. With bites from culinary heavyweights like Bobby Flay and Dean Fearing, all washed down with Moët & Chandon Champagne, the night already felt surreal. Then Willie walked out and delivered a private beachfront concert, marking the first time a major music star ever performed at the festival. In 2004, that moment changed everything and signaled that the South Beach Wine & Food Festival had officially arrived on the national stage.

2. 10th Anniversary Party with Alain Ducasse and Martha Stewart (2011)

The festival’s ten-year anniversary party in 2011 at 1111 Lincoln Road was nothing short of magical, a night hosted by the biggest names and powered by pure Miami energy. With culinary icons like Alain Ducasse, Martha Stewart, and Rachael Ray presiding over the rooftop, the evening felt like a victory lap for everything the festival had become. Set against the dramatic backdrop of the Herzog & de Meuron-designed garage, the party delivered over-the-top desserts, Champagne-fueled toasts, and unforgettable spectacle. It was bold, joyful, and perfectly embodied the spirit of the South Beach Wine & Food Festival at its peak. According to Schrager himself, for this epic tenth anniversary celebration, celebrity chef and baker Duff Goldman made a life-size drag queen cake that “lasted for months after until it molded and was tossed!”

3. KC and the Sunshine Band Performs (2011)

Harry Wayne “K.C.” Casey of KC and the Sunshine Band performed during the 2011 South Beach Wine & Food Festival. The performance featured the iconic disco frontman as part of the event’s festivities. It was great, and the audience loved him.

4. Miami Heat Players Take on Cooking Competition (2014)

Heat-ing up the festival in a way only Miami could, Miami Heat legends Shane Battier, Chris Bosh, and Dwyane Wade turned the Kitchen Heat competition into pure showtime in 2014. Teaming up with top local chefs, the Heat stars, who were just coming off their 2013 NBA Championship win, went head-to-head in a cook-off that had the crowd chanting and cheering. It was a major get for the festival, bringing the Heat in their prime into the mix and drawing in a new demographic.

5. Emeril Lagasse’s Stamp of Approval (2002)

From the very beginning, Emeril Lagasse was a cornerstone of the South Beach Wine & Food Festival and a driving force in shaping what it would become. He was there in 2002 when the festival launched in its modern form, lending his star power and credibility at a moment when SOBEWFF was still a one-day fundraiser finding its footing. He was the first major Food Network star to do SOBEWFF, and he was the gold seal of approval.

6. Food Network Stars Orchestrate Flash Mob at Alex Guarnaschelli’s Tribute Dinner (2023)

One of the most joyful surprises in festival history unfolded during Alex Guarnaschelli’s tribute dinner, when Food Network stars ditched their chef coats for a full-on flash mob. Orchestrated by Antonia Lofaso, the performance had chefs dancing to LL Cool J’s “Headsprung,” turning an elegant dinner into an instant party. Guarnaschelli happily jumped in on the fun. It was a first-of-its-kind moment for the tribute dinners.

7. The Chainsmokers Perform for 20th Anniversary (2021)

SOBEWFF’s 20th-anniversary celebration, postponed to 2021 due to COVID, was a full-blown affair marked by food, drinks, star power, and an unforgettable performance by the Chainsmokers. Hosted by the ultimate duo, Martha Stewart and Miami hospitality king David Grutman, the party at Fontainebleau Miami Beach perfectly blended fried chicken indulgence with high-energy glamour. With the Chainsmokers delivering an electric soundtrack, the night felt big, bold, and unapologetically Miami. It was the kind of milestone moment that proved the festival doesn’t just celebrate food, it throws a party like no other.

8. Guy Fieri Attends Festival Before Making It Big Time (2006)

Guy Fieri’s loyalty to the South Beach Wine & Food Festival is one of my favorite full-circle stories. Fresh off his 2006 Next Food Network Star win, before the fame and the fan frenzy, Guy showed up to SOBEWFF walking the grounds and handing out his own postcards, signing them one by one. He’s come back every single year since, growing alongside the festival as both became bigger than anyone could have imagined. From those early hustle days to a 2021 Tribute Dinner and a Hollywood Walk of Fame star, Guy’s journey is a testament to loyalty, gratitude, and the heart of this festival.

9. Bobby Flay’s First SOBEWFF Rained Out, But Show Must Go On! (2006)

The 2006 Grand Tasting is remembered as one of the festival’s most unforgettable tests of endurance. A monumental downpour completely soaked Day 2, with no tents in sight, as chefs and guests powered through sheets of rain. Chef and TV personality Bobby Flay standing there in the storm perfectly captured the early, gritty spirit of SOBEWFF, when nothing, not even Miami weather, could stop the show.

10. Mario Batali at the Dinner Honoring the King and Queen of Spain (2009)

What began as a formal dinner honoring the King and Queen of Spain at the Biltmore quickly went off the rails. Mario Batali, hosting the evening, turned the buttoned-up affair into something far more unpredictable. Batali took the mic as MC and promptly shocked the well-heeled crowd. Possibly under the influence that night, he launched into a profanity-filled tirade that left jaws on the floor. It was wildly inappropriate, completely chaotic, and impossible to forget. “A night that I will never forget — likely no one who attended will ever forget — it’s best that you Google it. I don’t think I can bear to repeat it. All I can say is, I guarantee you that the king and queen never did another wine and food festival ever again!”

11. The Gordon Ramsay Saga

Gordon Ramsay arrived, checked into the Loews, and then vanished. He never showed up to his scheduled events and was never heard from again during the festival. To this day, it remains one of SOBEWFF’s great unsolved mysteries.

12. Launching Burger Bash (2006)

Burger Bash debuted in year five of SOBEWFF, conceived and created by Rachael Ray. Twenty years later, it remains the single most popular event in festival history. What started as a fun idea became an absolute juggernaut.

13. Year One: Six Events, Six Thousand People (2002)

The very first SOBEWFF had just six events and an unexpected attendance of 6,000. We were completely unprepared for the demand. That moment made it clear this festival was going to be much bigger than anyone imagined

14. Food Network Comes On Board (2006)

Securing Food Network as the title sponsor in year three was a game-changing moment. It instantly catapulted SOBEWFF onto the national stage. From that point on, the festival entered an entirely new era

15. Alice Waters’ Missing Car

Landing Alice Waters in the early years was a massive win for the festival. We did everything we could to make her experience perfect, but her car and driver never showed up. Not exactly the first impression we had hoped for.

16. The Entire Today Show Goes Live (2016)

Hosting the entire Today Show live from SOBEWFF was a monumental milestone. With Enrique Iglesias performing on the beach, the festival officially went mainstream. It was one of those moments where everything clicked at once.

17. Reuniting the Mondavi Brothers

18. Hosting Jamie Oliver

Bringing Jamie Oliver to SOBEWFF was a huge international get. The press attention was intense, and expectations were sky-high. At that moment, he was one of the biggest names in food on the planet.

19. Alain Ducasse in Year One

Securing Alain Ducasse for the inaugural festival was the biggest get imaginable. His presence instantly gave SOBEWFF credibility on the world stage. It set the tone for everything that followed.

20. Anthony Bourdain and Eric Ripert Spin the Wheel

Anthony Bourdain and Eric Ripert hosted a demo that featured a provocative spinning-wheel game. It pushed boundaries in the best possible way. The crowd absolutely loved them.

21. Danny DeVito, Mario Batali, and Rachael Ray at DeVito’s

DeVito’s had just opened on the beach when we hosted a late-night Italian event there. With Danny DeVito, Mario Batali, and Rachael Ray all in the mix, the energy was electric. It may have been the best party we ever threw.

22. Launching FoodieCon

In year 22, SOBEWFF launched FoodieCon. It brought together the top food influencers from across the country under one roof. It marked a bold step into the festival’s next generation.

23. The Missing MC and Alton Brown Saves the Day

A scheduled MC missed their flight on the morning of a Tribute Dinner. With hours to spare, Alton Brown stepped in at the last possible moment. He saved the day without missing a beat.

24. The New York Times Feature by Alan Salkin (2008)

Alan Salkin’s New York Times feature was a turning point for SOBEWFF. It reshaped how the festival was perceived nationally. From that moment on, everything changed.

25. Paula Deen Rides Robert Irvine (2014)

During a live demo, Paula Deen decided Robert Irvine should give her a pony ride. He got down on all fours and obliged, to the crowd’s absolute delight. It was outrageous, hilarious, and peak early SOBEWFF chaos.