14. Jiles Perry Richardson
Even though Jiles Perry Richardson, the number 14 on our list of male singers with deep voices, or known as The Big Bopper died at the age of 28, he still managed to leave a mark in this world as one of the deepest voices among male singers. Jiles Perry Richardson was born on October 24, 1930, in Sabine Pass, Texas, and died on February 3, 1959, in Clear Lake, Iowa in a plane crash. Two months after his death, his son was born who 48 years after his father’s’ death, requested an autopsy on the body due to rumors on the internet about shots fired on the plane.