- 1996 – Began his professional stage career with East West Players, appearing in productions including The Taste of Kona Coffee.
- 1999 – Gained early mainstream recognition through his brief but memorable role in American Pie.
- 2004 – Became a leading man opposite Kal Penn in Harold & Kumar Go to White Castle, launching the comedy franchise that established him more widely.
- 2009 – Entered a major global franchise as Hikaru Sulu in the Star Trek reboot; the cast shared the Boston Society of Film Critics award for Best Ensemble Cast.
- 2014 – Starred as Henry Higgs in ABC’s Selfie, a landmark casting widely reported as the first Asian American male romantic lead in a U.S. romantic-comedy series.
- 2017 – Expanded his reputation as a dramatic actor with the acclaimed independent film Columbus, earning some of the strongest reviews of his career.
- 2018 – Headlined Searching, becoming the first Asian American actor to lead a mainstream Hollywood thriller; his performance subsequently received a 2019 Independent Spirit Award nomination for Best Male Lead.
- 2021 – Shifted into an action-heavy television lead as Spike Spiegel in Netflix’s live-action adaptation of Cowboy Bebop.
- 2022 – Expanded beyond acting with Troublemaker, his debut middle-grade novel, written with Sarah Suk.
