Sakurai began his career in the entertainment industry when he joined the Japanese talent agency Johnny & Associates in 1995 at the age of 13.

[1] For his work as an actor, singer and newscaster, Sakurai became one of the recipients of GQ Japan's Men of the Year award in 2009.

[5] From age three to ten, he did many extracurricular activities, including kendo, swimming, football, oil painting, calligraphy, and scouting.

[11] He began music lessons in early childhood, starting with the electric organ at age three and switching to piano in fourth grade.

[23][24] Sakurai is the designated rapper of Arashi and, although he had written rap lyrics (known to fans as Sakurap) for some of the group's earlier releases under the pen name "Show", his first major contribution was for the A-side song "Kotoba Yori Taisetsu na Mono".

These songs are "Movin' On," "Mada Ue o", "Taboo" (Sho Sakurai solo), "Let Me Down," "Sora Takaku", and "Summer Splash!".

[30] In February 2022, KAT-TUN announced the release of their digital single "Crystal Moment", as the theme song for NTV's coverage of the Beijing 2022 Winter Olympics, the rap lyrics were written by Sakurai.

[31] One year later, Sakurai was announced by KAT-TUN'S Ueda as a co-writer for two songs he would be singing in his solo concert in January 2024.

[35] On January 9, 2010, Sakurai co-starred with the other members of Arashi in the human suspense drama special Saigo no Yakusoku.

In 2001, he took part in his first drama series called Tengoku ni Ichiban Chikai Otoko 2 (天国に一番近い男 – 教師編, The Man Closest to Heaven 2) with Masahiro Matsuoka as his teacher.

His role as a student with two conflicting characters won him Best Newcomer in the 5th Nikkan Sports Drama Grand Prix Awards.

In January 2023, Sakurai appears in his 5th drama with NTV, after Yoiko no Mikata (2003), The Quiz Show 2 (2009), Saki ni Umareta Dake no Boku (2017) and Nemesis (2021).

In 2007, all the members of Arashi co-starred in their third movie together, Kiiroi Namida (黄色い涙, Yellow Tears), with Sakurai playing the role of an aspiring writer.

[50] In 2002, in the drama Kisarazu Cat's Eye, he took on the role of Bambi, a college student who becomes part of a burglar ring at the beckoning of his cancer-stricken friend Bussan (played by Junichi Okada) to make his final days worthwhile.

By the end of 2007, it was announced that he would star as Gan-chan in the Takashi Miike movie Yatterman, which was not released in theaters until the beginning of 2009.

[53] It was announced on June 8, 2010, that Sakurai would co-star with Aoi Miyazaki in the novel-based movie Kamisama no Karute (神様のカルテ, God's Medical Records), released in theaters in 2011.

In the first movie, Dr. Ichito Kurihara (Sakurai) was struggling with work life in a countryside hospital on the alert 365 days a year.

[57] On June 4, 2012, the movie version of the popular drama Nazotoki wa Dinner no Ato de (謎解きはディナーのあとで, lit.

The International Gala Premiere was held in Singapore on July 27, 2013, at Marina Bay Sands, where about 2,000 fans from Singapore, Thailand and other countries in the region were treated to face-to-face interactions with the main cast of Sakurai and his fellow cast members, Keiko Kitagawa and Shinai Kippei.

[107] In July 2010, Sakurai traveled to Romania, Germany, and Russia to do a special report on world poverty for NTV's 24-Hour Television, which was broadcast on August 29, 2010.

He interviewed former Soviet Union General Secretary and Nobel Peace Prize winner Mikhail Gorbachev about nuclear disarmament and poverty.

This one dealt with a historical look of the Great Eastern Japan Earthquake 5 years after, primarily, and other disasters around the world such as eruptions, landslides, floods and typhoons, and how to deal with them and prepare in order to save lives.

On this one, Sakurai and Ikegami talked about "Unexpected Japan", dealing with politics and its relationship to the Olympic Games, North Korea and the imperial family.

[112][113] A fourth installment of the series aired on May 4, 2020, where they talked about the "ultra difficult problems" facing Japan, like the coronavirus and all that happened around the pandemic, such as the closing of schools, delays in services and postponement of big events, like the Tokyo Olympics and Paralympics.

With the theme "clear and present danger", Ikegami and Sakurai, together with guests, talked about the ongoing investigation on coronavirus, its sequelae and the fight against it and new viruses.

It also included a talk about new AI technology and the risk of it being misused and abused, like in drones, which could be used as weapons, and the so-called "Deepfake", in which false images are used to replace someone else in order to commit crimes, like fraud.

[132] On May 13, 2012, NTV announced the appointment of Sakurai as the main caster for their coverage of the 2012 London Summer Olympics, from July 27 to August 12, 2012.

He was chosen, alongside his Arashi co-member Masaki Aiba, to host the NHK special program coverage for the Tokyo Olympics and Paralympics, celebrated from July 23, 2021.

[136] The NTV programs in which he has appeared covering rugby, including the sports section in News Zero, has had Arashi's song Brave, for which he wrote the rap, as background music.

[138] Sakurai was named host of the NTV program "One Rugby", a monthly special (September 6, 2019 – March 24, 2022; May 21, 2022, July 4, 2022) that analyzed the matches for both the local games and for the World Cup.