Sugimura was born on 24 August 1973 in Aichi Prefecture, Japan. His parents operated a weaving equipment factory and performed an amateur magician show titled “Magical Takeshi and China Yuriko”. He attended the Aichi Prefectural Bisai High School and was a member of the school’s baseball club.

Sugiyama commenced his career in entertainment in 1995 after graduating from the Nagoya branch of the Yoshimoto Kogyo talent school in 1994. He joined the Yoshimoto Creative Agency and was briefly in a manzai duo named “Frankfurt” with a fellow Yoshimoto member. In April 1995, he formed the duo “Reiketsu Sunday” with Noriyuki Sawahara. In 1998, they moved to Tokyo and joined the Asai Kikaku agency. Around the same time they changed the name of their act to “Mekadog” (lit. “Mechanical Dog”).

In January 2008, Sugiyama left Asai Kikaku, and in April, Mekadog disbanded. At this time Sugiyama started performing as a solo act. In April 2011, he joined the Sun Music management agency.

Upon the advice of a fortune teller, Sugiyama adopted the stage name Sugi-chan in November 2011. In March 2012, he was runner-up in the annual “R-1 Grand Prix” for solo comedians, finishing behind Kenji Tada of Cowcow. His “Wild darō?” (lit. “I’m wild, right?”) catchphrase brought him national attention and an increase in his workload. In September 2012, he fractured the T-12 vertebra in his spine when diving from a 10 m high platform while filming a variety show for TV Asahi.

In December 2012, his catchphrase “Wild darō?” was chosen as the “New/Vogue Word of the Year” by the U-Can correspondence education group.