In 1989, Sakurai started working at HAL Laboratory, where he created the game Kirby's Dream Land and the character Kirby at 19 years. He worked on more Kirby titles until he concieved and directed the original Super Smash Bros. on Nintendo 64.
After his further work on titles like Super Smash Bros. Melee and Kirby Air Ride, he resigned from HAL Laboratory on August 5, 2003, since he was seeking more freedom and was not happy with the structure of HAL, or the sequelization of the industry. After leaving HAL, Sakurai began working with Q Entertainment with Tetsuya Muzuguchi, which resulted in the creation of Meteos, a game for the Nintendo DS.
In September 30, 2005, he founded Sora, Ltd., a freelance video game company. Despite his departure from HAL, he still kept directing the following entries in the Smash Bros. series, as well as Kid Icarus: Uprising. His wife, Michiko Sakurai, has designed the menus and UI of several of his games. He also writes a weekly column in the Famitsu magazine.
- Kirby's Dream Land (1992) - Director, Chief Designer (as Masa Sakurai)
- Kirby's Adventure (1993) - Director & Game Designer
- Kirby Super Star (1996) - Director
- Super Smash Bros. (1999) - Director (Game Design, Planning, Direction, Motion Coaching, Kirby Original Design)
- Kirby 64: The Crystal Shards (2000) - Voice Actor (King Dedede)
- Super Smash Bros. Melee (2001) - Chief Director (Planning / Game Design; Motion, Movie & Game Direction; Data Design / Figure Explanation; Character Design for Kirby)
- Kirby: Nightmare in Dream Land (2002) - Chief Director
- Kirby Air Ride (2003) - Director
- Kirby & the Amazing Mirror (2004) - Special Advisor
- Meteos (2005) - Game Design
- Mushiking: The King of Beetles (2005) - Designer
- Meteos: Disney Magic (2007) - Meteos Original Game Design
- Super Smash Bros. Brawl (2008) - Director, Voice (King Dedede)
- Kid Icarus: Uprising (2012) - Director & Scenario
- Super Smash Bros. for Nintendo 3DS and Wii U (2014) - Director, Voice (King Dedede)
- Super Smash Bros. Ultimate (2018) - Director