Yujiro grew up in Kobe, Hyogo Prefecture, in Otaru, Hokkaido, and in Zushi, Kanagawa. His father, an employee of Mitsui O.S.K. Lines, was from Ehime Prefecture, and his mother was from Miyajima, Hiroshima. Yujiro attended Otaru Fuji Kindergarten and then Otaru City Inaho Elementary School. During his elementary school years he participated in competitive swimming and skied on Mt. Tengu. He then attended Zushi City Zushi junior High School, where he began playing basketball. He aimed to enter Keio Senior High School, but did not pass the entrance examination. He enrolled at Keio Shiki Boys' Senior High School, but in 1951 was admitted to Keio Senior High School. Afterward he entered the political science department of the school of law at Keio University, associated with the high school, but reportedly spent all his time playing around.

Wanting to become an actor, he auditioned at Toho, Daiei Film and Nikkatsu, but did not pass any of his auditions. However, in 1956, with help from producer Takiko Mizunoe and his brother Shintaro, he received a bit-part in the film adaptation of Shintaro's Akutagawa Prize-winning Season of the Sun, making his film debut. Afterwards he withdrew from Keio University to work for Nikkatsu, playing the lead in the film adaptation of Shintaro's novel Crazed Fruit.

At the 1958 Blue Ribbon Awards Ishihara won the prize for best new actor for the 1957 films Washi to taka and Man Who Causes a Storm. He would go on to become one of the representative stars of the Showa Era with his twin acting and singing career, but his life was one made harder by illness and injury.

In 1960 he married actress Mie Kitahara, his co-star in a number of films beginning in 1956 with Crazed Fruit.

Yujiro survived a 1978 oral cancer of the tongue, and a 1981 aortic aneurysm, supported by friends, family and his legion of fans. However he was later diagonised with liver cancer and died at Keio University Hospital in 1987 on July 17 at 4:26. He was 52 years old.

Throughout his life Yujiro used alcohol and tobacco, and ate meals that were lacking in vegetables; this unhealthy lifestyle is generally acknowledged as contributing to his early death.

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