Oguri made his TV debut in NHK's drama Hachidai Shogun Yoshimune in 1995.
In 1998, after playing the bullied and abused child Noboru Yoshikawa in the drama Great Teacher Onizuka, he started to be recognized by the public. His acting in that drama attracted attention, and led to bigger roles. In 2000, he played a deaf person in Summer Snow. In 2002, he starred in the popular drama Gokusen, in which he played a part of a bully, rather than the bullied, as he did in Great Teacher Onizuka. Oguri rose to prominence after his breakthrough role in 2005, as 'Hanazawa Rui' in the popular drama Hana Yori Dango. In 2007, he starred in the drama Hanazakari no Kimitachi e as 'Izumi Sano', co-starring with Toma Ikuta and Maki Horikita. In 2008, Oguri took up another lead drama role in Binbō Danshi by playing an optimistic poor college student named 'Kazumi Koyama'. In 2009, he appeared as lead in the drama Tokyo Dogs as American detective 'So Takakura'. He reunited with Hana Yori Dango co-star Mao Inoue for the drama Jūi Dolittle (獣医ドリトル), which began airing in October 2010. In 2012, he costarred with Satomi Ishihara in Fuji TV's Rich man, poor woman as a young wealthy man 'Toru Hyuga', which earned him the first Best Actor award in 74th Drama Academy Award. 1n 2014, Oguri starred in semi-historic anime live action drama Nobunaga Concerto, as both high school student 'Saburo' and the warlord 'Nobunaga Oda'. He continued to appear in other history-based dramas. In 2015, he reunited with Toma Ikuta after seven years in the TBS drama Ouroboros as 'Tatsuya Danno'.
Oguri appeared in 2006 as 'Shinichi Kudo' in the first Detective Conan live action movie Detective Conan: Shinichi Kudo's Written Challenge. In 2014, he was in the anime live action movie Lupin the third as the main character. And in 2017, he gave life to character Gintoki Sakata in the 1st. movie of the live action adaptation of anime Gintama, a role he reprised in 2 mini-series and another movie.
In November 2018, Oguri was cast in Godzilla vs. Kong, his Hollywood debut. The movie was released in theaters and on HBO Max in March 2021. He also appeared in films such as Sukiyaki Western Django, Let Me Eat Your Pancreas and Tsumi no Koe directed by Nobuhiro Doi (best known for directed Strawberry on the Shortcake, Be with You and Flying Colors)
In 2005, Oguri lent his voice as a voice actor in Fullmetal Alchemist the Movie: Conqueror of Shamballa, together with his brother Ryo. In 2009, he lent his voice as a voice actor once again in Wangan Midnight as 'Akio Asakura'.
He is also a director. His directorial debut was directing a commercial in 2009, but his major directorial debut on the big screen was a movie titled Surely Someday, which was released on July 17, 2010 nationwide in Japan. Oguri cast several of his good friends within the entertainment industry in the movie, such as Keisuke Koide as the lead starring role, Actresses Mao Inoue and Aya Ueto as cameos, and himself also making a cameo appearance in the movie.
On 2007, Oguri began appearing as navigator in Nippon Broadcasting System's radio program "All Night Nippon", which he carried (as "Oguri Shun no All Night Nippon") until 2010, with occasional special appearances after that. He was suggested to act as part of All Night Nippon for the PV of the song "Karensou" by newcomer group KEY GOT CREW.
In 2011, after the Tohoku earthquake and tsunami, he was part of a group of 71 actors and singers that appeared in the Suntory beverage company's commercials, singing the songs Miagete goran yoru no hoshi wo and Ue wo muite arukō. His singing voice has also been included in several stage appearances.
