As I stood inside the Carousel Club at Gulfstream Park in late January last year, it dawned on me: The Pegasus World Cup had arrived – not just as a major racing event but as an entertainment experience.

At the center of it all was the sound of music, which has become the big selling point of the event that will be headlined this year by renowned DJ Calvin Harris.

Looking around that swanky Carousel Club outdoor bar and lounge space, located at the top of the racing stretch at Gulfstream, I saw hundreds of 20-somethings sipping cocktails, making bets, mingling, dancing, and just vibing out. Unlike in past years, the party started much earlier in the day and took on the feeling of a true festival.

As the day went on, anticipation kept building at the Pegasus World Cup until close to sunset when Kygo and One Republic took the stage. From there, the Pegasus World Cup escalated into an epic South Florida dance party. I can’t wait to see what this year’s Pegasus World Cup, on Saturday, Jan. 27, has in store.

Since I’ve been fortunate to take in the Pegasus World Cup a number of times over previous years as well, I’ve put together a quick list of some of the most memorable musical and entertainment experiences at Pegasus.

THE MOST RECENT

2023 Pegasus World Cup

I can’t say enough about how well the entire day was scheduled and planned out for attendees. If you arrived at noon, there was already so much to get distracted by at Gulfstream Park. The races were just starting so you could make a bet, hit the bar, and then walk around the grounds. There were food trucks set up, a cigar rolling stand, and the sounds of music keeping the energy high between races. One Republic took it all to another level and had lots of people standing on couches, dancing, and singing every single lyric out loud. It was an absolute scene.  

THE THROWBACK

2022 Pegasus World Cup

I’m not one of those music snobs who always trashes on anything new but I will always defend the OGs, especially the legends of hip-hop. At the 2022 Pegasus, there was hardly anyone missing from that cluster of peak 1990s artists who brought us the sound and style of the genre, which has carried through to today’s music. Performing on the Carousel Club stage in 2022 were Ja Rule, Lil’ Kim, Mase, Jadakiss and Lil’ Cease. I know! You can relive some of it here.

THE WILDEST

2019 Pegasus World Cup

Snoop Dogg

Racing fans might remember this rainy revival of the Pegasus World Cup as the year City of Light and Bricks and Mortar won the featured races. But if you were in attendance at Gulfstream Park you’d probably also know it as the “Snoop Dogg” year. From the moment he stepped on Pegasus’ patented “celebrity blue carpet” to him calling “Rider’s Up” before the big race, a buzz followed Snoop around the track. Then, Snoop absolutely crushed it while performing in the LIV Stretch Village after the races. He made waiting out the rain that day well worth it.

THE ONE I WISH I HAD BACK

2020 Pegasus World Cup

This was one that I was on-site for at Gulfstream Park but I wasn’t able to make the show after the races — and boy, do I regret it. I’ve seen several videos from that night and the images could’ve been pulled from any major outdoor music festival filled with a sea of well-dressed, free-spirited fans loving every second of a show headlined by T-Pain and Nelly. Among those in attendance were a who’s who of major celebrities including Jennifer Lopez, Alex Rodriguez, and Vin Diesel.

THE BEST

2018 Pegasus World Cup

Post Malone

In the house that day were established musical royalty Pharrell Williams, Lenny Kravtiz, Ludacris, and Jermaine Dupri, but it was a then up-and-coming Post Malone that stole the show. I’ll admit, I hadn’t hard much of his music up to that point but you’ve got to give the event organizers credit for booking Post Malone as the headliner of the Pegasus World Cup just as he was beginning to blow up. Only a few months prior, he’d released his hit “Rockstar” and I’ll never forget the energy in the air near the stage from literally the first words he uttered on stage to the last note that night. It was one of the cooler performances I’ve seen anywhere and it was made even more special in that the setting (the top of the stretch at a Gulfstream) was both unique and intimate.

As a reminder, if you want to catch the show after the races this year, your best bet is probably going to be locking down a spot in the Carousel Club while you still can. As of this writing, the Carousel Club is nearly entirely sold out with the exception of VIP Tickets.