Deryck was in several bands before he met Steve Jocz in high school, but was in a band called "Doors of Draven" with Dave Baksh. His first band was called "The Powerful Young Hustlerz", a Hip Hop band that covered Beastie Boys songs. Deryck and Steve became good friends and started a band called Kaspir. The band consisted of Whibley as lead singer, Jocz on drums, Mark Spicoluk on bass, Dave Baksh and Marc Costanzo on Guitar. They later kicked Spicoluk out due to him getting into too much trouble, and Costanzo left to form the pop band, Len. Deryck then became the other guitarist. They changed their name from Kaspir to Sum 41 for a supernova show. They got Cone McCaslin to play bass in 1999 after having many other bassists. Among the first songs they wrote are "I Like Meat", "Astronaut", and "5-0 Grind"

In January of 2004, Deryck began dating fellow Canadian rocker Avril Lavigne. During the last part of Lavigne’s European Tour for the Bonez Tour shows, she and Whibley took a trip to Venice and got engaged. The couple married in a traditional ceremony on July 15, 2006, at a private estate in the California coastal city of Montecito, located about 87 miles (140 km) northwest of Los Angeles. Lavigne wore a Vera Wang gown, carried pearl-white Australian roses, and was walked down the aisle by her father. Whibley wore a Hugo Boss suit and was accompanied by four groomsmen, Steve Jocz (his best man), Jason "Cone" McCaslin, Avril`s older brother Matt Lavigne, and Sum 41`s close friend, Robb Dipple (well known for frequently accompanying Sum 41 to film their crazy antics). Lavigne`s younger sister, Michelle Lavigne, was one of the bridesmaids. About 110 guests attended the wedding, and their first dance as a married couple was to the Goo Goo Dolls song "Iris".[3] They currently live in Bel Air, Los Angeles, California.[4][5]

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