2004–2007: Cassie Ryan Leslie often saw Ventura at clubs and parties in late 2004. The two wrote a duet, "Kiss Me", and Leslie played a recording of it for music executive
Tommy Mottola. Leslie wrote and produced Ventura's first single, "
Me & U", in 2005. The song became a club hit in Germany. During this time,
Sean Combs 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 Ventura's debut album. She paid tribute to
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. Its lead single, "Me & U", peaked at number three on the
Billboard Hot 100, selling more than 1 million digital downloads. To promote her album, Ventura performed on
Total Request Live and ''
106 & Park: BET's Top 10 Live''. Her performances were described as "rocky" and "less-than-stellar", but Combs said that was due to her inexperience.
MTV News reported in June 2007 that, contrary to rumors, Bad Boy Records had not dropped Ventura after releasing two singles from
Cassie. Combs said she was working with producers
Kanye West and
Pharrell Williams on her second album. It was reported that Ventura was no longer collaborating with Leslie. Additional production on the album came from
Seven, LV, and Combs. Ventura said she had 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 on the album.
2008–2013: Acting debut and RockaByeBaby In 2008, Ventura made her acting debut as Sophie Donovan in the dance film
Step Up 2: The Streets. She also sang the lead single "
Is It You" on the
Step Up soundtrack. The song was released on November 13, 2007, and peaked at number 85 on the
Canadian Hot 100 and 52 in the UK's
The Official Charts Company. In July 2009, Ventura announced that her second studio album's title would be
Electro Love. Ventura described the album as "sensual" and said it would demonstrate more "independence" with a "difference in vocals, a little bit more personality". Three singles have been released from the album; "
Official Girl" featuring
Lil Wayne in August 2008, "
Must Be Love" featuring Combs in April 2009, and "
Let's Get Crazy" featuring Akon in August 2009. None of them charted in the United States. After several delays, it was announced in December 2009 that Ventura had signed a new record deal with
Interscope Records. She was featured in a spread in the August/September issue of
Bust, in which she said a new single would be released in the fall. At the time of an October 2010 interview with
HitQuarters, Mitchell said that Ventura had already recorded around 50 songs for the album and that she was taking her time because she wanted "it to be something that people are going to respect". On April 24, 2012, she performed the single live for the first time at BET's
106 & Park music video show. She concluded the performance with a brief dance number set to
Kanye West's remix of the song, along with four dancers. After the performance Ventura and 106 & Park were worldwide
trending topics on
Twitter and it received mostly mixed to positive reviews. The single "Balcony", featuring
Young Jeezy, was sent to U.S. urban radio stations on September 18, 2012. On September 13, 2012,
Nicki Minaj released the lead single off her re-release album
Pink Friday: Roman Reloaded – The Re-Up, titled "
The Boys", featuring Ventura. The song was sent to urban radios on September 25. A video was released on October 18. In July 2012, Ventura announced that she had been working simultaneously on her album and a new
mixtape,
RockaByeBaby. It was released on April 11, 2013, and was named the best mixtape of the year by
Dazed & Confused. The mixtape saw the release of "Numb" featuring Rick Ross on April 2, along with the song's video. "Paradise", featuring Wiz Khalifa, premiered on April 9, 2013, alongside the video on
BET 106 & Park. In April 2013 it was announced that Ventura was the face of the Summer 2013
Forever 21 collection.
2015–2019: Second studio album and other endeavors In March 2015, Ventura's then-boyfriend, Sean Combs, announced that he would return to producing and would produce songs for Ventura's second studio album. In 2016 it was announced that Ventura would return to acting, playing the lead role in the romantic comedy
The Perfect Match. It was released on March 11, 2016. In late 2017, she released the singles "Love a Loser" featuring American rapper
G-Eazy and "Don't Play It Safe". In January 2019, after ending her relationship with Combs and leaving Bad Boy Records, Ventura worked with producers Chris n Teeb and singer-songwriter
Ro James. In the summer of 2019, she released several singles on her Ventura Music label: "Moments" with The Code, "Excuses", "Hungover", "Don't Let Go", "Speaking Of", "Rollercoaster" featuring Ro James, "Teach Me", and "Simple Things". Ventura called the series of releases "Free Fridays". They served as a teaser for her second album's release. ==Artistry and public image==