After being signed to Arista Records in November 2000 upon the authorization of the label's CEO, Antonio "L.A." Reid, Lavigne moved to New York with the assistance of Reid. There, she began working on her debut album, Let Go, collaborating with a host of prime songwriters and producers.[6] For six months, the label set up Lavigne with two co-writers, who worked with her upon Arista's instructions. Reid expected Lavigne to record folk songs because she auditioned to them in a "balladic, 'new country'" type. However, the collective failed to click "with a girl who'd just discovered guitar-based rock".[7] For a year, nothing was working for Lavigne and was on the verge of getting dropped off Arista.[8] The management pitched her songs written by other songwriters, but she declined, insisting she wanted to write songs herself.[9] Lavigne relocated to Los Angeles, where she collaborated with songwriter-producer Clif Magness, who gave her ample creative control in the writing process. Lavigne and Magness wrote "Losing Grip" and "Unwanted", songs that she deemed reflective of her vision for the entire album.[10] However, Arista was not thrilled with the heavy-guitar laden songs that Lavigne was writing, prompting the label to look for other producers to match their demands.[11]
Two years since she signed the deal, Lavigne came to the attention of the three-piece production team The Matrix. Arista could not find the right direction for Lavigne, so the team's manager, Sandy Roberton, suggested that they work together.[12] According to member Lauren Christy, they had been listening to Lavigne's early songs and felt they contained "a Faith Hill kind of vibe". As soon as they saw Lavigne coming into their studio, The Matrix felt that her musical direction was incongruous to her image and attitude.[12] After talking to Lavigne for an hour, the singer said she wanted songs with punk rock inclinations.[7] They told her to come back the following day, and in the afternoon during that day, they wrote a song that evolved into "Complicated" and another song called "Falling Down". They played it to Lavigne when she came back the following day, inspiring her what path she should take.[12]
When Josh Sarubin, the A&R executive who signed Lavigne to the imprint, heard the song, he knew it was right for her. Lavigne presented the song to Reid, who agreed the musical direction Lavigne and The Matrix were taking, and set "Complicated" as the album's lead single.[12]