On Sept. 30, 2014, Prince released two studio albums simultaneously. While Art Official Age showcased the singer’s R&B side, Plectrumelectrum delved into the world of funk-rock. The latter LP also featured an appearance from future superstar Lizzo.

The singer/rapper, real name Melissa Jefferson, had begun her career in Houston. After performing in a rock band with minimal success, she moved to Minneapolis to pursue further musical opportunities. While there, she became part of a female hip-hop collective called the Chalice.

Around the same time, Prince was enjoying a renewed sense of feminism, exemplified by his latest backing band, the all-female 3rdEyeGirl. “We're in the feminine aspect now," Prince told Rolling Stone in 2014. "That's where society is. You're gonna get a woman president soon. Men have gone as far as they can, right? I learn from women a lot quicker than I do from men.”

With female empowerment at the forefront of his mind, the music icon was introduced to the works of Lizzo. Prince liked what he heard and invited the songstress and fellow Chalice bandmate Sophia Eris to collaborate on his song “Boytrouble.”

“He let us do whatever we wanted,” Lizzo remembered during a 2016 interview with Fuse. Describing the recording session as a “fairytale,” the singer recalled the instructions Prince gave her. “He summoned us to Paisley Park and said, ‘Treat this song as if it’s your own.’ Me and Sophia Eris treated it like it was our own and he left everything in. Even the scream. I do this scream on there and I was like, ‘What would Prince do? Yaaaah!’ And he left it in there.”

The track featured the duo providing vocals over a mesmerizing funk groove. Eris took the first verse, with Lizzo jumping on for a part-rapped, part-sung delivery on the second. Meanwhile, Prince took a backseat on the song, eschewing any vocals at all and instead letting his guitar do the talking.

The experience had a profound effect on Lizzo. “It was extremely surreal,” she admitted during an interview with Rolling Stone. “Mind you, I’ve been doing music my whole life and I hadn’t been very successful at a music career. Then as soon as I get to Minneapolis on a whim, I get to do something that a very small percentage of people have gotten to do.”

“There was this wonderful moment when we were in the recording booth and there was this mic with all these scarves,” the singer recalled. “It was so plush and I was like, ‘This is Prince’s mic. Can I get some essence?’ And I felt like I kind of transcended from just being just a vocalist into an artist. And that was a huge confirmation in what I was doing.”

The recording session also spawned a mutual admiration between the artists. Prince would invite the women back to Paisley Park to perform and later invited them to attend a private performance of his own.

“It was just Prince and a piano,” Lizzo recalled in an interview with 247HH. “He sang ‘Purple Rain’ and it was so beautiful. I wept. Everyone wept. It was this very special moment.”

Since that time, Lizzo has gone on to worldwide fame of her own. The singer’s latest LP, Cuz I Love You has earned commercial and critical success, buoyed by the popular singles “Juice” and “Truth Hurts.” Even as her star continues to rise, Lizzo has maintained a profound respect for Prince. During her performance at the 2019 MTV Video Music Awards, the singer paid homage to the since-deceased icon with several visual tributes.

“The biggest thing I learned from (working with Prince) was to stay true to your art,” Lizzo admitted in an interview with Extra given shortly after her VMA performance. “That is how you become an artist. You can be a musician, you can be a singer, you can play the drums, but when you’re true to your art, and the things that you create and you’re true to yourself, that’s when you become an artist. When you do it unapologetically. Keep it authentically you.”

Who Played With Prince the Longest?