She received her third award from Guillermo Mendoza Memorial Scholarship Foundation. In early June 1999, Santos starred in the Boots Plata-directed action comedy "Isusumbong Kita Sa Tatay Ko", appearing opposite Fernando Poe, Jr., which tells a story of a father-daughter relationship, Badong and Joey, the latter resentful with the idea of losing her father's love to another woman. The film received predominately favorable reviews and proved a commercial success. Sol Jose Vanzi of "Philippine Headline News Online" noted, "It's a match produced in celluloid heaven, because he [Poe] is king of Philippine movies while she [Santos] is considered today's drama princess." "Isusumbong Kita Sa Tatay Ko" marked the first Philippine-produced film to have reached and exceeded Php100 million in box office gross. The film's box office performance earned Santos a Guillermo Mendoza Memorial Scholarship Foundation Citation as Box Office Queen. For her next feature television drama, Santos starred in her titular weekly anthology "Judy Ann Drama Special" (1999). The making of the television drama also gave Santos significant acting experience; as she said, "It's so surreal that I'm doing my very own anthology. I've always dreamed about having one, though it came unexpectedly so soon. I'm ecstatic – and nervous altogether – but we've worked hard for each episode." On referencing her name for a drama series, she said, "I'm overwhelmed that a drama series has been named after me [...] you get to work with different actors, directors [...] we get to offer different stories each week." In September 2000, Santos released her self-titled debut album. Owing to the success of the lead-off single, "I Won't Last a Day Without You" (a cover of The Carpenters' song from the 1974 album "A Song For You"), the album was critically panned but received generally favorable commercial success, eventually certified platinum for thirty-thousand copies sold. Other singles that achieved moderate success included "You" (a cover of The Carpenters' song from the 1976 album "A Kind of Hush"), and "Longer" (a cover of Dan Fogelberg's song from the 1979 album "Phoenix"). In 2000, Santos had the lead role in "Kahit Isang Saglit". She portrayed Annie, a budding architect romantically torn between two best friends (played by Piolo Pascual and Leandro Munoz).