Ranking the three most memorable Pegasus World Cup musical performances

Great musical acts are a staple at events like the Super Bowl and the NBA All-Star Game but, for years, if you wanted to catch a buzz-worthy performance at a racetrack, you had to go to the Preakness Stakes – the second leg of the Triple Crown of horse racing.

That changed in 2017 when the same people who run Preakness (1/ST Racing) decided to bring an elevated experience (no shade if you like drinking and playing in the mud off the pitch at Preakness) to the south of Florida in the form of the Pegasus World Cup.

The 2022 Pegasus World Cup, taking place on Saturday, January 29 at Gulfstream Park, will once again feature top musical talent to accompany the day’s lineup of world-class racing. This year’s entertainment portion of the Pegasus sticks to its theme of “legends” with a cast that will take you back to the late 1990s, even if you weren’t alive back then. Hip-hop icons are scheduled to perform Rule Ja, Lil’ Kimand Mase, as part of DJ Cassidy’s famous “Pass the Mic” series.

Since I’ve been blessed with the Pegasus World Cup—both the races and the music—over the years, here’s my list of the three most memorable musical acts. This list, of course, will likely be revamped after this year’s event, which has the potential to blow up any musical performance we’ve ever seen at a racetrack.


Pegasus World Cup 2018

In the house that day sat musical royalty Pharrell Williams, Lenny Kravtiz, Ludacris and Jermaine Dupri, but it was a then-promising Post Malone who stole the show. I’ll admit I hadn’t heard much about his music until then, but you have the event organizers to thank for booking Post Malone as the Pegasus World Cup headliner at the time. even where it was beginning to explode. . Only months before he released his hit ‘Rockstar’ and I’ll never forget the energy in the air near the stage from literally the first words he spoke on stage to the last note tonight. -the. It was one of the coolest performances I’ve seen anywhere, and it was even more special in that the setting (the top of the stretch at Gulfstream) was both unique and intimate.


Pegasus World Cup 2019

Racing fans may 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 present at Gulfstream, you would probably also know it as the “Snoop Dogg” year. From the moment he stepped on Pegasus’ patented “celebrity blue carpet” until he called “Rider’s Up” before the big race, a buzz followed Snoop around the track. Then Snoop absolutely crushed it by performing in the LIV Stretch Village after the races. He made waiting for the rain that day was worth it.


Pegasus World Cup 2020

It was the one I was there for but couldn’t put on the show after the races – and my God, I’m sorry. I’ve seen several videos of that night and the footage could have been taken from any large 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 was a who’s who of big-name celebrities, including Jennifer Lopez, Alex Rodriguez and Vin Diesel.