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 vidéo sexy hilary duff producers Joel Madden and his brother, Benji, both members of Good Charlotte. The lead single, "Wake Up", 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 Still 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.^{Friederike Gnädig nue id="cite_ref-65" class="reference">[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 looking for projects outside the teen genre.^[67][68] She is also a model signed to IMG Models New York.^[69]

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 vidéo sexy hilary duff Man and Cheaper by the Dozen 2.^[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]

In 2007 Duff was photographed many times with NHL player Mike Comrie. Although Duff never revealed much about Friederike Gnädig nue the relationship, the couple were seen hugging and kissing, with Duff even attending some of Comrie's games. Comrie bought Duff a brand new $100,000 car for her twentieth birthday.^[102]

In January 2004, the second DisneyMania disc, DisneyMania 2, was released and featured a duet, "The Siamese Cat Song" with her sister. Another song, "Circle of Life", featured Duff and other Disney Channel stars. Duff and her sister recorded a cover of The Go-Gos' "Our Lips Are Sealed" for the soundtrack to A Cinderella Story, which also included two other songs by Duff. The video for "Our Lips Are Sealed" was popular on MTV's Total Request Live, but the cool pics.com song failed to chart on the U.S. Billboard Hot 100.^[30]

In January 2008, videos of Duff surfaced on YouTube, which showed her singing into her microphone at her concert in Mexico, but her voice was inaudible, leading viewers to believe that she was lip-syncing. Duff's representative defended her saying, "She was not lip-synching. It was faulty equipment. There was no sound coming out, but she was singing". He also added that Duff was not using her regular sound equipment, but instead was using locally provided equipment and that her microphone nina friederike sexy was inadvertently set on mute for the first few minutes of the performance.^[77][78][79]

In June 2006, when asked about her then-boyfriend Joel Madden, a native of Waldorf, Maryland, in an interview with Elle, Duff replied, "He's very real, like, he's from a pretty ghetto place in Maryland... I like that".^[59] Duff's "ghetto" comments sparked a mixture of mild offense and bemusement from residents of the Waldorf area, as the suburban, mostly middle-class town did not fall into the traditional haylie duff nue impoverished inner city concept of a ghetto.^[60] Duff later claimed she was referring not to Waldorf, but actually a section of Baltimore where Madden lived briefly as a young adult.^[61]