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Usher has been a music superstar for two decades. Since the early days of his career, he was seen as a heartthrob with an undeniable voice and equally undeniable dance talents. But when he was just starting out, he was just a rising R&B singer working with some of the industry’s biggest names such as Diddy and Al B. Sure!.

Usher | Kevin Winter/Getty Images for iHeartMedia

Usher rose to fame in the 1990s

Usher released his self-titled debut album in 1994. The album was executive produced by Sean “Diddy” Combs, who helped launch his friend The Notorious B.I.G. to stardom just a month earlier with the release of his debut album Ready to Die.

Usher became more popular in the late ’90s after the release of his sophomore album My Way. The album contained his first No. 1 hit single on the Billboard Hot 100 chart, “Nice & Slow,” as well as the top-two singles “You Make Me Wanna…” and “My Way.” He earned more No. 1 singles with his Grammy-winning 2001 album 8701, which spawned the hits “U Remind Me” and “U Got It Bad.” His 2004 album Confessions cemented him into one of the industry’s bestselling artists in the 2000s decade, with over 20 million copies sold and four consecutive No. 1 singles: “Yeah!”, “Burn,” “Confessions Part II,” and “My Boo.”

Usher wearing sunglasses
Usher | Emma McIntyre/Getty Images for iHeartMedia

Usher’s ‘first celebrity kiss’ was Monica

During his rise to fame in the 1990s, Usher crossed paths with singer Monica Arnold, who released her debut album Miss Thang in 1995. The pair were reportedly romantically involved for eight months that same year.

In a 2022 appearance on E!’s series Daily Pop, Usher revealed that Monica was in fact his first celebrity kiss. And not only that: he added that she was a good kisser. The two singers later collabed on the song “Slow Jam” from Usher’s 1997 album My Way.

Since then, Usher has become a father of four children, while Monica has three children of her own. Usher has been romantically linked to musical director Jenn Goicoechea since 2019; the pair welcomed their first child together in 2020, and their second in 2021.

Monica | Axelle/Bauer-Griffin/WireImage

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Usher wanted to date Aaliyah

When speaking on Daily Pop, Usher looked back on another romantic interest from the 1990s: the Princess of R&B, Aaliyah. But while he and Monica officially dated, he and Aaliyah were only friends and never struck up a relationship.

“Somebody that I was really good friends with that I wish I would have taken more serious because she was a really close friend of mine for a small amount of time and we just kind of disconnected was Aaliyah,” he said honestly. “I think I would’ve dated Aaliyah and we just didn’t get around to it. We just kind of talked but didn’t do it.”

Usher’s hit album 8701, which introduced the singer to audiences around the world, was released just two weeks before Aaliyah’s untimely death in August 2001.