Dick Winslow's parental units, Winonian Breazeala, a renowned writer, and Sidney R.Johnson, played a pivotal role in his early life. Upon graduating from Belmont High School in the city of angels, Los Angeles, Winslow made his film debut at the tender age of five. His impressive acting skills were first showcased on the stage, where he appeared in the notable play "Silver Thread" at the esteemed Egan Theatre in Los Angeles, and later in "The Emperor's Clothes" at the Belmont Theatre in the same city.
In addition to his captivating on-screen presence, Winslow was a multi-talented individual with a passion for music. He was well-versed in playing a wide range of instruments, including the pipe organ, piano, marimba, bagpipes, accordion, drums, and saxophone, among others. His impressive repertoire of musical skills only added to his already extensive filmography. By 1934, Winslow had already appeared in a staggering 75 films, solidifying his status as a prolific and talented actor of his time.