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In 1998, Monica's second album, The Boy Is Mine, earned her major international chart success.

Pushed by its Grammy Award-winning number-one hit title track, a duet with singer Brandy, it spawned two further Billboard Hot 100 chart-toppers, "The First Night" and "Angel of Mine", and established her position as one of the most successful urban R&B female vocalists to emerge in the mid to late-1990s.

The film was released on April 30, 2002 and in Felicity (2001) and American Dreams (2003) playing Mary Wells, singing "My Guy".

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The same year, she made a cameo appearance in the American comedy-drama film ATL, playing the Waffle House waitress.

In August 2008, Monica appeared in the Peachtree TV reality show special Monica: The Single which tracked the recording of the song "Still Standing" for her same-titled sixth studio album.

A year later, Monica channeled much of her heavily media-discussed experiences into the production of her third studio album, All Eyez on Me, her first release on mentor Clive Davis newly founded J Records label.

"I just wanted to give the people back something that had personal passion, instead of just, 'Oh, let's dance to this record'," she said about the issues worked into the tracks. "I don't think people wanted to hear a big fun record from me, after knowing all the things that I had personally experienced," Monica second-guessed her new material which saw both early and heavy bootlegging via internet at that time.

Monica also ventured into acting, with a supporting role in Boys and Girls (2000), and starring roles in television film Love Song (2000).