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Duff's first role in a theatrical motion picture was in Human Nature in 2002.
Most shows scheduled in the major cities were sold out.Duff also made several guest appearances in television shows, her first as a sick child in the medical drama Chicago Hope in March 2000. In a 2003 episode of George Lopez, she had a role as a makeup salesperson; she later reappeared in the show in 2005 as Kenzie, a feminist poet friend of the character Carmen (Masiela Lusha). While some critics praised Duff for appearing in a more mature and serious role than her previous films, the film itself was heavily panned and bombed at the box office. Several reviews were indifferent towards her acting performance and were critical of Duff's vocals, with critics pointing out what appeared to be her digitally enhanced voice. The same year, Duff received her first Razzie nomination for worst actress for her roles in Raise Your Voice and A Cinderella Story.In 2005, Duff starred in The Perfect Man, in which she played the eldest daughter of a divorced woman (Heather Locklear).
It attracted about 2.3 million viewers per episode. Her participation in the show made her popular among children between the ages of 7 and 14. Richard Huff, a New York Daily News critic, called her "a 2002 version of Annette Funicello". After Duff fulfilled her 65 episode contract with Lizzie Mc Guire, Disney considered expanding the franchise to films and a prime-time television series.
The plans failed, however, because Duff's representatives said she was not being paid enough for the proposed series. Duff also starred in the Disney Channel television film Cadet Kelly (2002), which became the network's most watched program in its 19-year history. In the movie, she plays a free-spirited girl who struggles in a strict military school.
Their mother moved with them to California, but their father stayed in Houston to maintain his business. Because she had been pursuing a professional acting career at such a young age, Duff was home-schooled. The sisters auditioned for several years and were cast in several television commercials.Early in her acting career, Duff primarily played minor roles.
In 1997, she appeared uncredited in the Hallmark Entertainment western miniseries True Women.