With Raynor, the group recorded their first demo, Buddha (1994), their debut album, Cheshire Cat (1995), as well as the gold-certified Dude Ranch (1997).

Since then, Raynor has performed with a wide variety of groups, including post-punk band the Wraith, and contributed to the charity StandUp for Kids.

The duo were initially inspired by Metallica, but found their material far too technical; they instead played "Twist of Cain" by Danzig and "London Dungeon" by the Misfits.

[1] While at the competition, new transfer student Tom DeLonge, who had been expelled from Poway High School for attending a basketball game while drunk,[1] performed an original song titled "Who's Gonna Shave Your Back Tonight?"

[5] The trio began to practice in Raynor's room (amid complaints from neighbors), which was soundproofed with empty egg cartons.

"It's difficult to describe, in words, the nauseous mix of fear and excitement that would hit me when I first started seeing lines of people wanting to hear us play," said Raynor.

[13] His parents allowed him to drop out of full-time school to move back and play with the band, but he would continue to finish his diploma by bringing homework on tour.

"[13] By March 1996, the trio began to accumulate a genuine buzz among major labels, resulting in a bidding war between Interscope, MCA, and Epitaph.

[17] Desperate for a break due to extended touring, the overworked band began to argue and tensions formed, centering largely around Raynor.

"[19] Shortly after the band released Dude Ranch, Raynor began to think outside of the situation, viewing the major label experience as nothing like he had hoped.

[20] Following a largely successful Australian tour in the spring, Hoppus and DeLonge presented an ultimatum: quit drinking or go to an in-patient rehab.

[28] By the time the deal went through, Raynor was having disputes with the group and quit; the band later released their debut album as Death on Wednesday through Vagrant in 2000.

Recorded live over the course of a day, Raynor has described it as dark comedy, "a Black Sabbath, Ramones, and "Weird Al" Yankovic milkshake.

"[30] Raynor fulfilled a long-held ambition to work with Nirvana producer Jack Endino on an extended play recorded with The Spazms in 2004.

[citation needed] In the 2000s, he began contributing to a charity called StandUp for Kids, an outreach organization that helped street and homeless youth.

[28] In 2003, a rumor circulated on the Internet that Raynor had been shot dead; he addressed the hoax via a letter he e-mailed to the sites in question, that instead directed the attention to the StandUp for Kids organization.

[31] Raynor appears in the music video for the song "Wing of Night", although he didn't take part in the writing process.