Chester Charles Bennington was born on March 20, 1976, in Phoenix, Arizona. His mother was a nurse, while his father was a police detective who worked on child sexual abuse cases. Bennington took interest in music at a young age, citing the bands Depeche Mode and Stone Temple Pilots as his earliest inspirations, and dreamed of becoming a member of Stone Temple Pilots, which he later achieved when he became their lead singer. Bennington suffered sexual abuse from an older male friend when he was seven years old.

Bennington was frustrated and almost ready to quit his musical career altogether when Jeff Blue, the vice president of artists and repertoire at Zomba Music in Los Angeles, offered him an audition with the future members of Linkin Park. Bennington quit his day job at a digital services firm and took his family to California, where he had a successful audition with Linkin Park, who were then called Xero. He managed to record the song for his audition in a day, missing his own birthday celebration in the process. Bennington and Mike Shinoda, the band's other vocalist, made significant progress together, but failed to find a record deal. After facing numerous rejections, Blue, now a vice president of artists and repertoire at Warner Bros., intervened again to help the band sign with Warner Bros. Records.  On October 24, 2000, Linkin Park released their debut album, Hybrid Theory, through Warner Bros. Records. Bennington and Shinoda wrote the lyrics to Hybrid Theory based on some early material. Shinoda characterized the lyrics as interpretations of universal feelings, emotions, and experiences, and as "everyday emotions you talk about and think about." Bennington later described the songwriting experience to Rolling Stone magazine in early 2002, "It's easy to fall into that thing - 'poor, poor me', that's where songs like 'Crawling' come from: I can't take myself. But that song is about taking responsibility for your actions. I don't say 'you' at any point. It's about how I'm the reason that I feel this way. There's something inside me that pulls me down."  Bennington primarily served as Linkin Park's lead vocalist, but occasionally shared the role with Shinoda. All Music Guide described Bennington's vocals as "higher-pitched" and "emotional", in contrast to Shinoda's hip-hop-style delivery. Both members also worked together to write lyrics for the band's songs.

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