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5 Things To Know About Cassie’s Music Career And Why She Only Released One Album Under Diddy

By Maurice - 2025/05/16
5 Things About Cassie's Music Career And Why She Only Released One Album Under Diddy

Long before Cassie and Diddy were facing off in a courtroom, the singer was a rising star signed to Bad Boy Records. Fans have often questioned how her signing with Diddy’s label first came about, as well as why she released music so rarely following the success of her debut album. From her breakout moment to her recent claims that her career was being held back due to Diddy’s “freak-offs,” here’s what to know.

RELATED: Beatings Diddy’s Staff Knew About, Self-Harm & Her Tell-All Book: Cassie Continues Testimony In Federal Trial (LIVE UPDATES)

Cassie’s Ex, Ryan Leslie, Helped Her Get The Deal

Cassie didn’t just stumble into the music industry; she had a man who claimed he would make her a star. Before Diddy even entered the picture, Cassie had signed to her then-boyfriend Ryan Leslie. He owned the record label NextSelection Lifestyle Group. While based in New York, the two had been cooking up music in the studio, including her debut single, ‘Me & U,’ which would go on to become her biggest hit to date.

Leslie was already a heavyweight, with a catalog of hits under his belt. And according to The New York Times, he brought in Tommy Mottola to manage Cassie under the executive’s management company. When ‘Me & U’ dropped, it shot up the charts, peaking at No. 3 on the Billboard Hot 100.

The general public was clearly feeling the song, and that’s when Leslie reportedly ran into Diddy at a club. He pitched him a partnership that would see Bad Boy Records team up with NextSelection to push Cassie’s already-finished debut album. Diddy agreed and signed her shortly after. Cassie’s self-titled album dropped in 2006, and she was officially on the map.

Cassie & Ryan Leslie Go Their Separate Ways

Within two years, Cassie wasn’t just Diddy’s artist; she was his leading lady. The tea on how things ended with Leslie remains unclear, but he’s always kept it classy. In a 2009 VLADTV sit-down, Leslie said, “I love Cassie. I fell in love with her, I fell in love with the music, I fell in love with her family.”

But when pressed about their fallout, he hinted at “specific characters” messing things up. Fast-forward to 2019, on The Breakfast Club, Leslie spilled that Cassie had started ghosting studio sessions for her second album with him, during which time she had already started dating Diddy.

@livefromtheplaza

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♬ Very Sad – Enchan

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Other Notable Songs And Projects Released By Cassie

Cassie was more than just a one-hit wonder, though. In her early Bad Boy days, she definitely had herself a run in the music industry. In 2008, she starred in ‘Step Up 2: The Streets,’ and sang the film’s soundtrack single ‘Is It You.’ That same year, she linked with Lil Wayne for ‘Official Girl’’ which was meant to be the lead single of her sophomore album.

However, that project was shelved for reasons that remain unknown. Furthermore, ‘Official Girl’ was her first track without Leslie’s pen or production, indicating a big switch-up in her career.

#2

Diddy And Cassie Collaborated

In 2009, Cassie and Diddy dropped their one and only collaboration together, titled ‘Must Be Love.’ The track was given the music video treatment, with both of them appearing in the visuals. Though the song wasn’t a major hit for either of them, Diddy and Cassie were sending a message, letting it be known they were in love they were through their music.

#3

Cassie Tries A Comeback?

After a brief hiatus, Cassie came back in 2012 with the Nicki Minaj collab on ‘The Boys,’ followed by the release of her electro-pop track ‘King of Hearts.’ Then, in 2013, she gagged us with her RockaByeBaby mixtape, her first full project since her debut, featuring ‘Numb’ with Rick Ross. By 2017, she was experimenting with ‘Love a Loser’ (ft. G-Eazy) and ‘Don’t Play It Safe,’ leaning into a more experimental sound.

#4

Cassie Says Diddy Held Her Back BIG TIME

In Diddy’s sex trafficking trial, she reportedly testified that her music career was “stifled” during their relationship. According to Business Insider, Cassie recorded hundreds of songs while with Diddy, but most never saw the light of day. She alleged Diddy’s control over her life and career kept her from focusing on music, claiming she was too caught up in his “freak-offs.”

#5

“He chose what was next for me, basically,” she said on the stand. Cassie also revealed those “freak-offs” went from once a week to way too often, overshadowing her intent to be an artist. Additionally, she claims she didn’t get paid for all that unreleased music either. “When I wasn’t working on my music, I was recovering from partying,” she said, with “partying” being the “freak-off” sessions. “That was a big chunk of my life.”

RELATED: Beatings Diddy’s Staff Knew About, Self-Harm & Her Tell-All Book: Cassie Continues Testimony In Federal Trial (Day Three)

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Maurice Cassidy

Maurice Cassidy

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