The 150th running of the Preakness Stakes wasn’t just about fast horses and fine hats — it was a spectacle of music, celebrity, and celebration that brought the Pimlico Race Course to life like never before. For its milestone event and final race before a long-awaited reconstruction, the Preakness pulled out all the stops with headline performances from Grammy-winning artists Wyclef Jean and T-Pain.

Set in the heart of Baltimore, the historic track became a star-studded stage on May 17, 2025, where race fans and celebrities collided for a day of high energy and glamour. Wyclef Jean kicked off the party with a vibrant, genre-blending performance that mixed hip-hop, reggae, and rock — all while giving a shout-out to Belinda Stronach, the 1/ST CEO who recently sold the racetrack to the state for $1 in a landmark deal tied to massive redevelopment plans.

Wyclef didn’t hold back. His performance was bold, dynamic, and filled with celebratory undertones as he helped set the mood for what would become a historic farewell to the old Pimlico. “This place has soul,” he told the crowd. “And tonight, we honor that history.”

After the races concluded — including jockey Umberto Rispoli’s thrilling victory aboard Journalism — it was T-Pain’s time to shine. The multi-platinum artist delivered an electrifying nighttime performance, performing hit after hit like “Buy U a Drank,” “Bartender,” and “Up Down,” much to the delight of VIP guests who had gathered for the exclusive post-race celebration.

T-Pain’s performance wasn’t just a concert — it was a party. The VIP section was filled with athletes, reality stars, and business moguls, all vibing to the beat. Among those spotted in the crowd were former NFL greats like Ray Lewis and Cam Newton, NBA star Carmelo Anthony, and former MLB pitcher CC Sabathia. The presence of high-profile athletes added even more gravity to the night, highlighting the cultural clout of the Preakness.

Also joining the festivities were familiar faces from the world of reality TV — including cast members from shows like Summer House, The Bachelor, and Love Is Blind. With Bravo stars mingling beside sports icons and local officials, the Preakness felt less like a traditional horse race and more like a Coachella-style social event, all under the banner of Maryland’s most iconic race.

Governor Wes Moore and Baltimore Mayor Brandon Scott were also in attendance, lending the event an air of official significance. The two public figures were seen enjoying the performances, chatting with celebrities, and paying tribute to the historic significance of the racetrack.

One particularly notable attendee was celebrity chef and restaurateur Bobby Flay. But Flay wasn’t just there for the food or the music — he was celebrating his horse Candied’s big win in the Allaire du Pont Distaff Stakes earlier that day. The victory added a personal triumph to the festivities and gave Flay even more reason to raise a glass during the after-party.

That after-party, by the way, was one for the books. Held at the exclusive Elk Room, the event brought together the who’s-who of Baltimore nightlife. Belinda Stronach, whose bold decisions over the past year reshaped the future of Pimlico, was spotted dancing as her own son took over the DJ booth. It was a surreal and symbolic moment — the past, present, and future of Pimlico blending into one unforgettable celebration.

The Preakness Stakes of 2025 will be remembered not just for its races or winners but for the way it said goodbye to an era. With reconstruction on the horizon, the night served as a poignant yet joyous farewell to the Pimlico many have known for decades.

Even the performers seemed aware of the night’s significance. T-Pain, known for his auto-tuned vocals and party anthems, paused mid-set to thank the crowd and reflect on the power of legacy. “You can rebuild a track,” he said, “but you can’t rebuild memories. Let’s make this one count.”

That energy carried through the rest of the evening, as laughter, dancing, and toasts filled the Elk Room and echoed across Baltimore. It wasn’t just an end — it was a celebration of everything Pimlico has been and everything it might become.

In the days following the event, social media lit up with clips from both Wyclef and T-Pain’s performances. Fans praised the event’s energy, diversity, and seamless blend of music and sports culture. “Best Preakness ever,” one Instagram user wrote, sharing a video of T-Pain performing against a backdrop of flashing lights and waving hands.

If there was any doubt about the cultural relevance of the Preakness Stakes in the 21st century, the 2025 edition shattered them. It proved that horse racing, when paired with world-class entertainment and a touch of star power, can remain vibrant and relevant in a changing world.

As Pimlico closes its gates for renovation, one thing is certain: it won’t be easy to top the final night of the old track. T-Pain, Wyclef, and a guest list straight out of a Hollywood party gave it a send-off worthy of its legendary name.