| 1968 | Signed to Apple Records and released his self-titled debut, becoming one of the first American artists on the Beatles' label and planting his flag in the folk revolution sweeping the United States. |
| 1970 | 'Sweet Baby James' broke him to a mass audience, the album's lead single 'Fire and Rain' reached the Top 5 on the Billboard Hot 100 and made Taylor the emblem of the singer-songwriter movement he would go on to lead. |
| 1971 | Recorded Carole King's 'You've Got a Friend' for 'Mud Slide Slim and the Blue Horizon'; the single hit #1 on the Hot 100 and earned Taylor a Grammy for Best Pop Vocal Performance, Male. |
| 2015 | 'Before This World' became his first #1 album on the Billboard 200, more than four decades into his career, and sent him back out on the sold-out arena tours that affirmed his enduring global reach. |
| 2020 | 'American Standard', Taylor's take on the Great American Songbook, debuted at #1 on the Billboard 200, making him one of the few artists to place a Top 10 album in each of the past six consecutive decades. |
| 2020 | Won the Grammy Award for Best Traditional Pop Vocal Album for 'American Standard' at the 63rd Annual Grammy Awards, his sixth career Grammy. |
| 2022 | Performed to a sold-out crowd at Tanglewood with his All-Star Band during a North American tour that also included sold-out dates at Wrigley Field and Fenway Park. |
| 2024 | Marked 50 years since his Tanglewood debut with two-night anniversary concerts at the Koussevitzky Music Shed, then received the Tanglewood Medal from the Boston Symphony Orchestra in recognition of his career achievements. |
| 2025 | James Taylor and His All-Star Band headlined a 24-city summer tour across North America, with Tiny Habits as support, hitting amphitheaters from Phoenix to Boston and returning to Tanglewood for a fourth of July performance. |
