2007–2009: Wild Hope and Amanda Leigh
In early 2006, Moore said that she missed her music career and that singing is what she was the "most passionate about". In 2004, Moore signed with Sire Records after her contract with Epic ended, but she left the label in May 2006 because of creative differences. She signed with The Firm Music, owned by EMI, in July that year, calling her recording contract "especially exciting", and saying that she left Sire because she did not want to "follow the mainstream", but rather have "complete control and freedom" over her music.
Moore co-starred with Diane Keaton, Gabriel Macht and Tom Everett Scott in the romantic comedy Because I Said So. The film was released on February 2, 2007, it was a financial success, earning $69 million worldwide at the box office. Reviews were generally negative. Later that year, Moore co-starred with John Krasinski and Robin Williams in the romantic comedy License to Wed which was released on July 3, 2007. The film received overwhelmingly negative reviews but was a financial success, grossing $43.8 million domestically and $69.3 million worldwide. Variety called the film "an astonishingly flat romantic comedy, filled with perplexing choices", but called Moore's performance "appealing".
On September 24, 2007, Moore guest-starred in the CBS sitcom How I Met Your Mother in the third-season premiere episode "Wait for It". Later that year, she co-starred with Billy Crudup, Tom Wilkinson and Dianne Wiest in the romantic comedy Dedication. She played Lucy Reilly, a struggling children's book illustrator who falls in love with Henry Roth (Crudup). The film premiered at the 2007 Sundance Film Festival and received mixed reviews from critics.
Moore's fourth studio album Wild Hope was released on June 19, 2007, and Moore collaborated with record producer John Alagía and a number of musicians on it, including Chantal Kreviazuk, Lori McKenna, Rachael Yamagata and The Weepies. Moore stayed alone in a house in Woodstock in Upstate New York while recording the album in late 2006. Moore performed the album's lead single "Extraordinary" at the Brick Awards on April 12, 2007, and launched a tour in the summer of 2007.
The album received mixed to positive reviews from critics. Billboard said that "Wild Hope is the gratifying sound of a singer finally finding her comfort zone. Gone is the sugary pop of Moore's early career, replaced instead by thoughtful musings on love and life…an album full of subtle, but undeniable hooks." The album debuted on the U.S. Billboard 200 at #30, selling 25,000 copies the first week of its release, according to Billboard. The album also reached No. 9 on The Top Internet albums. To date, the album has sold over 120,000 copies in the U.S. and more than 350,000 copies worldwide. On February 23, 2008, Moore released the album in Australia, and subsequently toured with musician Ben Lee and the West Australian Symphony Orchestra in Western Australia, supporting inaugural American Idol winner Kelly Clarkson on her tour.
Moore began working on her fifth studio album Amanda Leigh in 2008. Recording sessions for the album took place around December 2008 in Boston, Massachusetts with singer-songwriter, record producer, pianist, and guitarist Mike Viola. The album's lead single "I Could Break Your Heart Any Day of the Week" was released on March 17, 2009, and its music video premiered on April 20, 2009, on Yahoo! Music. The single failed to have an impact on any major charts.
Amanda Leigh was released on May 26, 2009. On the album, Moore said, "The music is all a reflection of me now, not somebody else's choices." To promote the release, Moore visited a number of talk shows, performing "I Could Break Your Heart Any Day of the Week" on shows including The Ellen DeGeneres Show and The Tonight Show with Jay Leno. On May 26, 2009, she performed songs from the album at Amoeba Music in Hollywood. The album received generally positive reviews. Time magazine called the album "impeccably recorded". An article on the album by Paper magazine said, "Mandy (in the album)... shows real thoughtful and emotional depth." Paper finished by saying that "Moore is a far better musician than she's often given credit for." It debuted at number 25 on the Billboard 200, selling 16,000 copies in the U.S. during the week of its release, and at number 4 on the Top Independent albums chart. To date, the album has sold an estimated 100,000 copies. The album was recorded just prior to Moore's marriage to musician Ryan Adams and was her final album for over ten years.