Bennington first gained prominence as a vocalist following the release of Linkin Park's debut album, Hybrid Theory (2000), which was a worldwide commercial success.

"[7] Chester Charles Bennington was born in Phoenix, Arizona, on March 20, 1976,[8] to a mother who worked as a nurse and a father who investigated child sexual abuse[9] cases as a police detective.

[10] Bennington took an interest in music at a young age, citing the bands Depeche Mode and Stone Temple Pilots as his earliest inspirations.

[18] Bennington and Mike Shinoda, the band's other vocalist, made significant progress together but failed to find a record deal and faced numerous rejections.

[19][20] 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.

[29] In 2005, Bennington co-founded Dead by Sunrise, an electronic rock band from Los Angeles, California, with Orgy and Julien-K members Amir Derakh and Ryan Shuck.

The setlist included original Stone Temple Pilots songs, as well as their first single with Bennington on vocals called "Out of Time", which debuted on May 19 and was available for free download via their official website.

It was later announced by Bennington and the band in an exclusive KROQ interview that he was officially the new frontman of Stone Temple Pilots and discussed the possibility of a new album and tour.

[45] Althea Legaspi of Rolling Stone wrote, "Bennington's voice embodied the anguish and wide-ranging emotions of the lyrics, from capturing life's vulnerable moments to the fury and catharsis found in his belted screams, which he would often move between at the turn of a dime.

"[44][46] Bennington stated that he was influenced by Stone Temple Pilots, Alice in Chains, Arcade Fire, Circle Jerks, Descendents, Deftones, Jane's Addiction, Metallica, Fugazi, Refused, Ministry, Minor Threat, Misfits, The Naked and Famous, Nine Inch Nails, Nirvana, Pearl Jam, Skinny Puppy, Soundgarden, and A Tribe Called Quest.

[53] Chester and Talinda Bennington were harassed by a cyberstalker, who was later found guilty in 2008 of tampering with the couple's email and other personal information, as well as sending threatening messages, and was sentenced to two years in prison.

[62][63] This tweet resurfaced in July 2020 after Linkin Park sent Trump a cease and desist order for using "In the End" in an ad for his re-election campaign that year.

[68][69] In 2011, Bennington fell ill again, and Linkin Park was forced to cancel three shows and reschedule two from the A Thousand Suns World Tour.

[87] The band was due to record a live performance of their single "Heavy" on the show, but Bennington decided instead to play "One More Light" after hearing the news about Cornell's death.

[87] On May 26, 2017, a week after his Kimmel performance, Bennington sang Leonard Cohen's song "Hallelujah" at Cornell's funeral in Los Angeles with Brad Delson on guitar.

[94] On August 27, during the 2017 MTV Video Music Awards ceremony,[95] Jared Leto received media attention for his tribute to Bennington and Chris Cornell.

Coldplay's Chris Martin paid tribute to Bennington during the band's North American tour concert at MetLife Stadium, playing an acoustic version of "Crawling" on piano.

[102] Producer Markus Schulz made a trance remix of the Linkin Park song "In the End" as tribute to Bennington after his death, which he debuted at Tomorrowland.

Often those types of people have so much pain and torture inside that the last thing they want is to contaminate or break the spirit of others... As real and transparent as our conversations would be, he was always the one projecting light on the shadows.

[111][112] While describing the success of Bennington and Linkin Park, AllMusic's Andrew Leahey said, "Although rooted in alternative metal, Linkin Park became one of the most successful acts of the 2000s by welcoming elements of hip-hop, modern rock, and atmospheric electronica into their music ...focusing as much on the vocal interplay between singer Chester Bennington and rapper Mike Shinoda.

[7] Fred Durst, lead singer of Limp Bizkit, stated that if it were not for Bennington's voice and his words, nu metal "would never have reached the masses and affected so many lives".

[105] The New York Times' Jon Caramanica commented that Bennington's ability to "pair serrated rawness with sleek melody" separated him from other contemporary singers, and also from the artists he was influenced by.

As Bennington acquired influences from industrial and hardcore punk acts, the journalist believed this was the factor that made Linkin Park survive the "rise and precipitous fall of the rap-rock era", calling the musician "a rock music polymath".

[114] Mikael Wood of the Los Angeles Times argued, "Perhaps more than Linkin Park's influential sound, Bennington's real artistic legacy will be the message he put across – the reassurance he offered from the dark.

"[117] While talking about Linkin Park's popularity, Corey Apar, of AllMusic, commented, "Bennington's oft-tortured vocals became one of the most distinctive in the alternative rock scene.

"[118] Writing for the Guardian, Ben Beaumont-Thomas noted, "Bennington's decision to sing clearly and openly was, therefore, more radical than he is given credit for, and indeed more socially valuable."

[120] In the same topic, William Goodman from Billboard said Bennington and fellow musicians Chris Cornell and Scott Weiland "helped define a generation of the hard rock sound, who were tied together artistically and personally".

[123] In 2020, during a Twitch live-stream, Mike Shinoda confirmed the existence of an unreleased Linkin Park song, titled "Friendly Fire", which features vocal tracks Bennington recorded during the One More Light sessions.

"[128] A Decade Underground Bennington executive-produced the 2012 debut EP Us–You for Los Angeles hard rock band Hellflower, which is fronted by his long-time friend and Director of Activities (D.O.A.)

[139] Bennington was working with Church on developing an upcoming television show, Mayor of the World, with executive producer Trip Taylor.