Cheri Dennis first appeared on the Mase tracks "No Matter What", "All I Ever Wanted" and "If You Want to Party" from his album Double Up (1999), after running into Diddy during a party in New York. After appearing briefly on Puff Daddy's Forever album ("Is This the End? (Pt. 2)") also in 1999, in 2001 she reappeared signed to Bad Boy Entertainment with her first solo track "So Complete" from the P. Diddy and The Bad Boy Family album "The Saga Continues...". Afterwards she was heard on several mixtapes, before finally releasing her first single, the Ryan Leslie produced track "I Love You", in fall 2005. The music video was filmed in March 2006 before premiering on BET's 106 & Park on May 1. "I Love You" peaked at #38 on Billboard's Hot R&B/Hip-Hop Singles & Tracks. Dennis' second single "Portrait of Love" peaked at #55 before her debut album In and Out of Love finally released in February 2008, debuting at #74 on the Billboard 200. Her song "Ooh La La" was originally used as an opener for Making The Band 3, which suggested that the final band recorded the song.