Duff's third album, Most Wanted (2005), comprised her favorite tracks from her previous two albums, remixes, and new songs inspired by pop-rock musicians such as The Killers and Muse. In an appearance on Total Request Live, Duff stated that it was not a greatest hits album, but that her label told her it was time to release a new album. She had more creative control over Most Wanted compared to her previous releases, co-writing the new material with producers Joel Madden and his brother, Benji, both members of Good Charlotte. The lead single, "Wake Up", nina friederike gnaedig photo sexy became Duff's highest peaking single on the U.S. Hot 100 at the time,^[30] and its video received heavy rotation on MTV. The video for the second single, "Beat of My Heart", was also popular, but the single itself did not chart in the U.S.^[30] The album debuted at number one on the Billboard 200^[54] and became her third number one debut in Canada. An Italy-only compilation, 4Ever, was released in 2006. Duff recorded new songs for her movie, Material Girls, which included a Timbaland-produced cover version of Madonna's "Material Girl" with her sister.^[55]

During her Most Wanted tour, she performed in Guadalajara, Mexico, where she filmed a brief appearance on the soap opera Rebelde. She was also the guest star on The Andy Milonakis Show for its third season premiere in 2007.^[66] In April 2008, Duff was offered the lead role of Annie Mills in the CW Network's Beverly Hills, 90210 spinoff, but she turned it down because she was more interested in hilary pics.com looking for projects outside the teen genre.^[67][68] She is also a model signed to IMG Models New York.^[69]

In 1999, Duff appeared in a supporting role in the television film The Soul Collector, which was, nina friederike gnaedig photo sexy based on a Kathleen Kane novel and starred Bruce Greenwood and Melissa Gilbert. Duff won a Young Artist Award for "Best Performance in a TV Movie or Pilot (Supporting Young Actress)" for her role in the movie.^[10]

In 2003, Duff got her first major role in a feature film when she was cast alongside Frankie Muniz in Agent Cody Banks. The film received positive reviews and was successful enough to spawn a sequel, in which Duff did not participate. The same year, Duff reprised her role as Lizzie McGuire for The Lizzie McGuire Movie, which exceeded box office expectations, earning $42.6 million at the US box office^[18] and $55 million hilary pics.com worldwide.^[19] It received mixed reviews, with certain critics calling it "an unabashed promotion of Duff’s image, just as Crossroads was for Spears",^[20] while other reviews were generally positive and encouraging.^[21][22][23] Later that year, Duff played one of the 12 children of Steve Martin and Bonnie Hunt in the family film Cheaper by the Dozen, which remains her highest grossing film to date.^[24] She reprised her role in the sequel to the film called Cheaper by the Dozen 2 (2005), which failed to be as successful as the original film and was panned by critics.^[25][26]

In 2004 Duff began dating Good Charlotte singer Joel Madden.^{trailers of what are dreams made of by hillary duff class="reference">[90]} After a long period of tabloid speculation, Duff's mother Susan announced their relationship in a June 2005 interview for Seventeen magazine.^[94] In a June 2006 interview with Elle, Duff stated

In 2004 Duff starred in the romantic comedy A Cinderella Story. Though the reviews were mostly negative, the film went on to become a moderate box office hit, and critics were impressed by Duff's performance.^[38][39] A Cinderella Story earned $70,067,909 worldwide and was a commercial success.^[40] Later that year, hilary duff naked she starred in the film Raise Your Voice, her first role in a drama film. While some critics praised Duff for appearing in a more mature and serious role than her previous films, the film itself was heavily panned, with the Las Vegas Weekly writing: "Effortlessly combining Duff's bad acting and bad singing with bad writing and bad direction, Raise Your Voice is an insulting waste of time that begs to be silenced."^[41] Several reviews were indifferent towards her acting performance and were particularly harsh towards Duff's vocals, with critics pointing out what appeared to be her digitally enhanced voice.^{[42][43][44][45]} The film received a lukewarm response at the box office, and is Duff's least successful film commercially, with total theater receipts of $14,867,514.^[46] The same year, Duff received her first Razzie nomination for worst actress for her roles in Raise Your Voice and A Cinderella Story.^[47]

In 2005, Duff starred in The Perfect Man in which she played the eldest daughter of a divorced woman (Heather Locklear). The film received mostly harsh reviews and did not live up to box office expectations, grossing $19,770,475 globally.^[48][49] In the same year, Duff was again nominated for a Razzie Award, for The Perfect Man and Cheaper by the Dozen 2.^{trailers of what are dreams made of by hillary duff id="cite_ref-razzies2005_49-0" class="reference">[50]} The 2006 satirical comedy Material Girls, in which she co-starred with her sister Haylie, was also not well received by critics, grossing only $16,907,561 worldwide.^[51][52] The film, directed by Martha Coolidge and co-produced by Madonna's independent film production company Maverick Entertainment, starred the Duff sisters as wealthy siblings who must fight to reclaim their fortune following a scandal. Duff along with her sister Haylie, received two more nominations for Razzie awards for their role in the film.^[53]