Kenny Chesney, Ashanti and Ja Rule

Out of context, Kenny Chesney seems like a strange addition to this picture of hip-hop stars Ja Rule and Ashanti.

The two collaborated often in the early 2000s and maybe even (probably?) dated (she says probably not). “Mesmerize” and “Always on Time” are two examples of Ja Rule and Ashanti’s chemistry. So what in the heck is a country singer doing in their space?

It turns out he was invited.

Twenty years ago, Ashanti held court at a since-shuttered New York City club called Crobar. Her concert was filmed for the Oxygen network. The Oxygen: Custom Concert found her performing solo songs between collabs with Ja Rule and Irv Gotti.

Chesney was also on the bill, singing some of his biggest hits after singing Oleta Adams’ “Get Here” with Ashanti. A 43-minute-long video of the set can be found on YouTube (and below) — go ahead and skip ahead to 25:00 to watch the start of his segment.

“He’s dope. He’s just got this aura about him,” Ashanti says in a pre-recorded interview. “A lot of people love Kenny.”

For his part, Chesney named Ashanti as an artist he always wanted to perform with. Here he gets his chance. His warm, patient vocals prove to be a great fit for the soaring vocalist.

After “Get Here,” Chesney gets to show off with one of his own (fan-selected) songs, “When the Sun Goes Down.”

Here we can add some context to why the country star was chosen. His career was on fire at the time; in fact, two weeks earlier he won his first CMA Entertainer of the Year award.

Additionally, country music and hip-hop were merging in ways never seen before. Two months before the show, Tim McGraw and rapper Nelly dropped “Over and Over” and garnered significant critical acclaim and fan response. Ironically, Nelly and Ashanti are now married.

These days, we think nothing of it when a rapper and a country star team up, but back then it was uncharted territory and a huge risk professionally.

In the two decades that followed, Chesney would rarely share a song with an artist from the pop music world (Dave Matthews and Pink are two notable exceptions), and his music didn’t stray from his established canon of poignant ballads and beachy country-rockers.

Billy Dukes is a Senior Editor and Executive Producer of Video Content at Taste of Country. He specializes in country music interviews, trend analysis and the Secret History of Country Music. Additionally, Billy covers Yellowstone, 1923 and related television shows through the Dutton Rules podcast. To date, he’s written more than 13,000 articles for Taste of Country and produced over 3,000 videos for the Taste of Country YouTube channel.