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Cassie Ventura was born in 1986 in New London, Connecticut; the daughter of a Filipino father and a mother of African-American, Mexican and West Indian descent. She attended the Williams School, a preparatory school, located on the Connecticut College campus. At age 14 Cassie began modeling, and when she was sixteen, she was modeling for local department stores, Delia's fashion catalog, and Seventeen. Cassie also briefly appeared in R&B singer Mario's "Just a Friend 2002" music video.

Ryan Leslie spotted Cassie at clubs and parties in late 2002 frequently. The two wrote a duet called "Kiss Me", and after recording the track, Leslie played the song for music executive Tommy Mottola. Mottola offered Cassie a management deal, and Leslie signed her to NextSelection Lifestyle Group, his music-media company he founded with online marketing partner Rasheed Richmond. Leslie wrote and produced Cassie's first single, "Me & U", in 2005. The song became a club hit in Germany. During this time, Diddy heard "Me & U" in a club, and Leslie convinced him to partner his Bad Boy Records with Leslie's NextSelection imprint for the release of Cassie's debut album.  Ryan Leslie produced most of the album, which is a mix of R&B/hip hop/pop. Ventura said in an interview, "I rap, I sing, I do my R&B, I do my slow songs and stuff that the girls will love, I have a down South joint, I have a rock song that I did with my girls this band called Pretty Boys." She paid tribute to her Filipino culture by incorporating OPM sounds into some of the ballads. The album, Cassie, was released on August 8, 2006 and sold 321,000 copies in the United States. The album's lead single "Me & U" peaked at number three on the Billboard Hot 100, selling more than 1 million digital downloads. To promote her album, Cassie performed on Total Request Live and 106 & Park: BET's Top 10 Live. Her performances were described as "rocky" and "less-than-stellar", but Diddy said that it was due to her inexperience. He said that he would be "with her through her development", and that he has no "question on her ability [to sing]". Cassie addressed the events on her MySpace page, saying that she is aware that her performances were "pretty bad", and that she was "still getting over stage fright".  MTV News reported in June 2007 that contrary to rumors, Cassie had not been dropped from Bad Boy Records after releasing two singles from her self-titled debut album. Diddy said that she was in the studio working with producers Kanye West and Pharrell Williams on her second album. It was also reported that Cassie was no longer collaborating with Ryan Leslie, who had produced the majority of her debut album. However, the singer later stated that she was open to collaborating with Leslie again. According to Bad Boy A&R Daniel 'Skid' Mitchell, rather than largely relying on the one songwriter-producer, the new album's mix of writers and producers, as well as her own co-write input, makes it a more personal record for her. Additional production on the album came from Seven and LV, as well as Diddy himself. Cassie said that she had also collaborated with Akon, The Neptunes, Danja, Eric Hudson, The Surf Club and Rob Holiday, although she was not sure which tracks were going to be included on the album. Commenting on the number of producers on the album, Cassie said that she "collaborated with a lot of different producers and a lot of different writers, which was an amazing opportunity for me, because on my first album, one producer [Ryan Leslie] straight through...which was fun, but it was nice to experience other people."
Cassie Ventura