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At age 15, Matsuda was offered the role of the desirable young samurai Kanō Sōzaburō in Nagisa Ōshima's 1999 film Taboo. The role helped boost him from an entirely unknown actor to a film star, earning him a Japanese Academy award "Newcomer of the Year", as well as "Blue Ribbon", "Kinema Junpo", and "Yokohama Film Festival" Awards for the "Best New Actor". Since appearing in Taboo, Matsuda has played a wide range of roles, from the high school student Kujo in the 2001 film Blue Spring to the rock star Ren Honjo in the 2005 film Nana. In February 2013, it was revealed that Matsuda would play the part of a Japanese gangster in the sequel to the 2012 Indonesian film The Raid, named Berandal.

In 2020 portrayed Ryūnosuke Akutagawa in the film A Stranger in Shanghai. It depicts Akutagawa's time in as a reporter in the city. Since then, Matsuda has continued to work steadily across film and television. His notable award-winning period remains centered on his earlier career — most notably his Best Actor win at the 37th Japan Academy Film Prize in 2013 for The Great Passage, alongside a Best Actor win at the 2nd Hainan Island International Film Festival in 2019 for the film Shadow.

More recently, his credits include the films Ichigeki (2023), Who Were We? (2023–2024), and Transcending Dimensions (2025). On television, he starred in the Netflix drama Asura (2025), based on Kazuo Kikuta's play, and in Tokyo Salad Bowl (2025). His film Disaster was released on February 20, 2026, and was also selected for the competition section of the San Sebastián Film Festival. In January 2026, Matsuda took on his first-ever leading role in a TV Asahi drama with Hey Detective, Your Backpack Is Open!

He also appeared in UNDERGIRL a first movie from UNDERCOVER production, a superhero film released in Shibuya.