As I came up on a milestone birthday this past year, my wife asked me if there’s anything I wanted to do to celebrate. I was totally ready to make a suggestion and it was actually a pretty easy call. I wanted to go to a music festival.

We ultimately ended up traveling to Austin and spent three days at Austin City Limits. It was spectacular. As exhausted as I was after three days of dancing, drinking, and inhaling dirt, taking in all that good music only made me hungry for more. Now, I couldn’t be more excited to follow up that experience with what is low-key one of the chillest music events of the winter — Pegasus World Cup day at Gulfstream Park.

Scheduled for Saturday, Jan. 28, the music and entertainment lineup at the Pegasus serves as a complement to world-class racing action that takes place on the racetrack. I was pumped when it was announced that Kygo and One Republic will be playing the Pegasus World Cup this year. If you’re making plans to be there, you can expect the headliners to take the stage at the trackside Carousel Club sometime after the races finish around 6 p.m.

Since I’ve been fortunate to take in the Pegasus World Cup a number of times over the years, I’ve put together a quick list of some of the most memorable musical acts. Let’s start with the most recent.

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 Pegasus last year, there was hardly anyone missing from that peak 90s group of artists that brought us the sound and style of the genre that 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 below:

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 “Riders 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 heard 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 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 up Carousel Club tickets while they’re available. In addition to the music, your tickets also get you full open bar before the show (and during the races) from 11:00 a.m. to 4:00 p.m., complimentary bites and a $25 wagering credit compliments of 1/ST BET.