Preakness 2024: Headliner Jack Harlow lovin’ on Baltimore as he shouts out Lamar Jackson, Orioles

The rapper from Louisville, Kentucky, worked in shoutouts to Baltimore throughout his 18-song set, which capped a rainy day of music and horse racing at Pimlico.

Jack Harlow finally made it to Baltimore.

His first show in the city was supposed to be in 2020 at The Ottobar, an intimate Charles Village venue. But that gig was canceled by the COVID-19 pandemic, the rapper told a much bigger audience at Pimlico Race Course on Saturday night.

He was scheduled to perform at the Preakness Stakes in 2021, but dropped out after his DJ was charged with murder.

Harlow’s first Charm City appearance ultimately came Saturday as the headliner of Preakness LIVE, the daylong music festival that runs parallel to the Preakness Stakes.

“Today is my first day in Baltimore, Maryland, ever,” he confessed. “This is my first time setting foot in this city, and I’ve heard a lot of great things.”

The 26-year-old rapper from Louisville, Kentucky, worked in shoutouts to Baltimore throughout his 18-song set, which capped a rainy day of music and horse racing at Pimlico. The sun began to peek through the clouds shortly before he took the stage.

Harlow changed a line in the hit song “What’s Poppin’” to incorporate a nod to Baltimore’s baseball team: “I’m at the club with the baseball team, me and the Orioles sharing a section.”

He praised Ravens quarterback Lamar Jackson, and the team’s Super Bowl chances: “I saw the MVP was on the track today. … It might be your year this year.”

He even asked the question many city natives ask when trying to gauge whether someone is truly Baltimore born-and-raised: “Who’s from Baltimore here? Like, who went to high school in Baltimore?”

Across a tight, 40-minute set, Harlow worked the crowd, complimenting a fan’s hat and later jumping off the stage to come face-to-face with the audience. His set spanned hits like “First Class,” “Industry Baby” and “Lovin On Me.”

Festivalgoers covered sundresses and striped button-downs with ponchos for much of the overcast day, which was punctuated by scattered showers that muddied the grassy Pimlico infield. Preakness LIVE kicked off at 11:15 a.m., bringing a day full of sets from artists and DJs including Chantel Jeffries, Frank Walker, Gryffin and Channel Tres.

Crystal Demas, of Columbia, and her friends planned a “moms’ day out” to take in the music, fashion and horse racing.

“I’m here for the drinks, I’m here for the packages, I’m here for the theme, the ‘fits; I’m definitely here for the fashion, and the food is bomb,” Demas said.

But the group was most excited about seeing Harlow perform.

“We’re here for the horses, but we’re here for Jack,” said Brittany Booker, of Pennsylvania. “We’re going to fangirl over Jack.”

Britt Arnett, of Catonsville, also proclaimed himself a “huge Jack Harlow fan.” The festival put him in a sunny mood despite the gloomy weather.

“I normally hate the rain,” he said, “but last year it was raining sideways and this is still the best time I’ve ever had. So I couldn’t wait to come back.”

Arnett said he had planned to see Harlow in Pennsylvania during the pandemic, but COVID canceled the show. Faced with the prospect of finally witnessing one of his favorite artists perform, he said he was “feeling euphoric but also anxious.”

“I’m just excited he made it.”