| 1997 | "My Way" broke Usher into the mainstream, with "Nice & Slow" reaching No. 1 on the Billboard Hot 100 and "You Make Me Wanna..." establishing him as one of R&B's most compelling young voices. |
| 2001 | "8701" sold eight million copies and yielded back-to-back Hot 100 No. 1 singles "U Remind Me" and "U Got It Bad"; "U Remind Me" won the Grammy Award for Best Male R&B Vocal Performance. |
| 2004 | "Confessions" debuted at No. 1 with 1.1 million first-week sales and spent nine weeks atop the Billboard 200; "Yeah!" featuring Lil Jon and Ludacris held No. 1 for 12 consecutive weeks, and Usher won three Grammys at the 47th ceremony including Best Contemporary R&B Album. |
| 2008 | Billboard ranked Usher the 21st most successful Hot 100 Singles Artist of all time, recognizing nine No. 1 hits as a lead artist and 16 Top 10 entries on the Hot 100. |
| 2010 | "Raymond v. Raymond" topped the charts with "OMG" spending eight weeks at No. 1 on the Hot 100, with Billboard later naming Usher the No. 1 Hot 100 artist of the entire 2000s decade. |
| 2021 | Sold out all 20 shows of his debut Las Vegas residency at The Colosseum at Caesars Palace, then launched a second residency at Park MGM titled "My Way, The Las Vegas Residency" celebrating the 25th anniversary of his breakthrough album. |
| 2023 | Wrapped up his combined Las Vegas run of 100 shows across two residencies, cementing his status as one of the most successful residency headliners in the city's history. |
| 2024 | Headlined Super Bowl LVIII halftime show at Allegiant Stadium, drawing widespread critical acclaim, then released ninth studio album "Coming Home" featuring collaborations with Burna Boy, H.E.R., 21 Savage, and Jungkook. |
| 2024 | "Past Present Future" tour launched in support of "Coming Home," expanding from 24 original dates to 58 shows due to overwhelming ticket demand, running through 2025 with a final stop in London. |
| 2026 | Co-headlined "The R&B Tour" stadium run with Chris Brown, kicking off at Empower Field at Mile High in Denver for a major summer stadium circuit. |