Dylan was born in Toronto, Ontario, Canada. His first role was playing Streeter in the Canadian children's series The Doodlebops for two episodes at the age of 10. He then played roles in movies such as The Devil's Mercy, Booky & the Secret Santa, Everything Is Connected, Breakfast with Scot, For All the Marbles and made a guest appearance in The Dresden Files as Scott Sharpe. At the age of 13 he played 'Big Ben' in the Family Channel series The Latest Buzz. He also voiced 'Wolfy' in the series Super Why!. He then appeared in other roles until his big break in 2009 with How To Be Indie as Marlon Parks and then went on in 2010 to play the lead character in the Family Channel series Wingin' It.
In 2010, Everett reprised his role in Wingin' It as Carl Montclaire for another thirteen episodes. He reprised his character as Marlon Parks to film a second series of YTV's How To Be Indie, which premiered in Canada's fall 2010 and he reprised his role as Carl Montclaire for another season in the Family Channel series, Wingin' It that premiered in January 2011.