In 2002, after a break and some touring, Crow released C'mon, C'mon. Musically unlike any of her other records, the project had a more pop feel. Videos and promotional photos also found Crow more scantily clad than ever before, in bikinis and hot pants. Crow stated she was making a statement that women over 40 were still sexy. Whether a statement or a marketing tool, C'mon, C'mon spawned hits in "Soak Up the Sun" and 2002 Best Female Rock Performance Grammy winner "Steve McQueen". Crow also performed the song "Safe & Sound" from this album at a television benefit for the victims of September 11th, 2001 terrorist attacks. 2002 also found Crow collaborating with Stevie Nicks, and releasing a successful single called "Picture" with rumored boyfriend Kid Rock. Later Crow said they were good friends.
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Crow opposed the 2003 invasion of Iraq, wearing a shirt that read "I don't believe in your war, Mr. Bush!" during a performance on Good Morning America and posting an open letter explaining her opposition on her website. Her public stance attracted so many supporters of the war to her website that the message board was closed for a number of days.
In 2003, Crow released a greatest hits compilation called The Very Best of Sheryl Crow. It featured many of her hit singles, as well as some new tracks. Among them was the ballad "The First Cut is the Deepest" (a song originally composed and performed by Cat Stevens), which became her biggest radio hit since her first, "All I Wanna Do," which hit #2 in 1994.
2004 saw Crow appear as a musical theater performer in the Cole Porter biopic De-Lovely. Her performance within the film of the Porter classic "Begin the Beguine" was critically panned by film reviewers.
She is now dating cycling great Lance Armstrong, almost 10 years her junior. The couple have announced they are engaged to be married in Spring 2007. The "celebrity couple" aspect of the relationship landed them on the talk shows celebrity circuit (she appeared with him on the Oprah Winfrey Show and with Barbara Walters) and helped keep her in the public eye.
Crow was a main stage act at Lilith Fair and has contributed many songs to movie soundtracks and special projects that were never made available elsewhere, among them: "D'yer Maker" (Encomium: Led Zeppelin Tribute), "La Ci Darem la Mano" from Don Giovanni (Pavarotti & Friends For War Child), and "Resuscitation" (The Faculty). Her album Wildflower which had a more orchestral feel than her previous albums was released in September 2005 to mixed reviews. It spawned a minor hit "Good is Good" and though the album debuted at #2, it quickly dropped making it one of her least successful albums to date.