USHER entered public consciousness in the early ’90s as a smooth, baby-faced teenager whose lack of vocal bass didn’t quite match up with the sexual undertones of his music. His 1994 self-titled debut was foundational in furthering Combs’ development of a new R&B sound that took production cues from hip-hop—but much of the album felt like an artist figuring out his sound in real time. When he returned three years later with a deeper voice, a jawline that was no longer boyishly round, and musical direction from Atlanta producer extraordinaire Jermaine Dupri, the Usher Raymond we’ve grown to know and adore was introduced to the world. His sophomore album, My Way, traded those overtly hip-hop beats from The Hitmen for more fitting silky arrangements from Dupri and R&B maestro Babyface, which made a world of difference. “After that first album, I really decided that I wanted to do things my way,” USHER told Apple Music’s Estelle in 2022, and he found the inspiration and validation to do so in the form of—who else?—Frank Sinatra. “Hearing him tell his story, hearing him express how, ‘Hey, listen, good, bad or whatever it might be, I did it my way.’ To me, that's where I was in my life at the age of 16, 17. It was almost like the permission that I needed. So I was like, ‘I want to name this album My Way. I want to have something that I can say I'm proud of.’” On the album’s lead track “You Make Me Wanna…” USHER convincingly built on the soul music tradition of bellowing out to a prospective lover who makes you reconsider the lacklustre relationship you’re currently enduring—a concept he landed on after being stymied by a Dupri beat. “Me and my homie were playing basketball outside,” he said. “I had a Jeep back then, so I would crank the record up, playing out in the middle of the street, and would just listen to this track over and over and over again, like, ‘Yo, what do you think this is making you feel?’ He's like, ‘I don't know. I ain't never heard nothing like this. This shit is crazy.’ So I came back to the studio. I was like, ‘Yo, after about three days of listening, I don't know what I want to talk about.’ And then the more we just hung out, kicked it at the studio, he overheard a conversation I was having with this chick—and I'm in a relationship. I'm a scum guy.” “Slow Jam,” a cover of a song that Babyface wrote for Midnight Star in the ’80s, recruited another teenage R&B phenom in Monica for a sultry ballad. And a Lil’ Kim appearance on “Just Like Me” provided USHER with useful grit. A sweet falsetto, guitar strums that acted as ad libs, and dramatic heavy breathing helped “Nice & Slow” effectively melt the hearts of teenage girls through Walkman headphones and radio speakers—but maybe its most seductive move was USHER spelling out his name. “I was really looking for something to introduce myself,” he said. “So I was like, ‘I want a song that's going to spell my name out: They call me U-S-H-E-R R-A-Y-M-O-N-D.’ That was like Snoop's ‘Snoop Dogg’ or Eminem's ‘My Name Is’. For me, it was my introduction to the world over an R&B classic record that people celebrate all over the world.” All throughout My Way, it became clear that he was more than the potential that was teased a few years prior. Now with proven juggernauts in his corner, USHER was becoming the model for a young star in the genre—clean-cut, a big smile, designer goggles cocked to the side of his head, and a voice that resonated with Black youth. More than two decades after USHER found his voice, he had a clear sense of what the album meant, not just to him personally, but to pop music in general. “R&B assists us in all of these other areas, whether it became authentic hip-hop, or rock ’n’ roll, or any of it,” he said. “My version of it is a combination of those things. If you hear a rock guitar in a song, that doesn't make it a rock song, that makes it a rock solo. If you hear a rap in a song, that doesn't make it a rap song, that makes it a song that has new arms and connects with a bigger audience. So My Way gave me that opportunity to spread my wings and also to explore some things that I was inspired by.”