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In 20, Matsumoto was given his first lead stage play roles in Eden no Higashi.
Matsumoto gained further popularity as an actor in 2002 when he starred in the first season of Gokusen with Yukie Nakama, Shun Oguri, Tomohiro Waki, Hiroki Narimiya and Yuma Ishigaki.
He portrayed the lead character Yori Yūki, a high school student who falls in love and develops a romantic relationship with his younger twin sister.
In 2008, Matsumoto took on his first jidaigeki role in a re-make of Akira Kurosawa's The Hidden Fortress, Kakushi Toride no San-Akunin: The Last Princess, with award-winning actors Hiroshi Abe, Kippei Shiina and Masami Nagasawa.
His portrayal of the troubled but highly intelligent student, Shin Sawada, drew acclaim and won him Best Supporting Actor at the 33rd Television Drama Academy Awards..
In the same year, Matsumoto took another high-profile role in the live-action adaptation of manga series Kimi wa Pet as Takeshi "Momo" Goda, starring opposite Koyuki.
Soon after, TBS decided to end the Hana Yori Dango series through a film.
Hana Yori Dango Final, which hit the big screen on June 28, 2008 in Japan, became a box office hit.
Although the majority of Matsumoto's solos for albums and concerts are written by Arashi's staff, he has contributed lyrics for two of his solos: "La Familia" for the 2004 Arashi! and "Naked" in 2008 for the album Dream "A" Live under the penname "Jun".He also starred in the film Tokyo Tower as a womanizer with a preference for older women with Junichi Okada the same year.In 2007, Arashi starred in their third movie together Kiiroi Namida while Matsumoto was cast in the independent film Boku wa Imōto ni Koi o Suru with Nana Eikura as his co-star.but his breakthrough did not come until 2001 when he was cast as Hajime Kinda'ichi in the third season of Kinda'ichi Shōnen no Jikenbo, taking over the role from Tsuyoshi Domoto and co-starring opposite Anne Suzuki.In 2002, Arashi co-starred in their first movie together called Pikanchi Life is Hard Dakedo Happy in 2004.