Yoshida spent six years in Osaka during his grade school days, and later grew up in Hino, Tokyo.
While a student at St. Paul High School, he saw the Shakespearean comedy "Twelfth Night" by the Kumo Theater Company and decided to become an actor.
He was valued as an actor capable of performing the roles required of foreign classics such as Shakespeare and Greek tragedies, and was a regular in Yukio Ninagawa's productions.
These performances attracted attention, which led to an increase in his appearances in films, his first starring role being in Tokyo Sentimental.
In October 2016, he succeeded Yukio Ninagawa as the second artistic director of the Sai no Kuni Shakespeare Series.