McCracken was born in Provo, Utah, and grew up in Orem, Utah. He was raised in a Mormon family with three sisters (Katie, Melanie, Rachel) and one younger brother (Joseph Taylor). McCracken has stated that he read quite voraciously growing up, due to the influence of his mother, who was a schoolteacher. At age 12, he started playing the trumpet in a local band called “I’m With Stupid”. He attended Timpanogos High School for a brief time, before dropping out at 16.
Eldest son of the household, Bert enjoyed a happy home life as a child, but as he grew into a teenager his and his parents’ views conflicted. He rebelled against his parents and against their Mormon religion, eventually leaving the Latter-Day Saint Church. He dropped out of high school; soon after, he left his home at the age of 16. For some time he was homeless until he found enough money for an apartment, moving in with then-girlfriend Kate.