| 1995 | Launched his recording career with his self-titled Spanish debut album, which produced five consecutive number-ones on Billboard's Hot Latin Tracks chart and won the Grammy Award for Best Latin Pop Performance at the 39th Grammy Awards. |
| 1999 | Crossed over to English-language pop with the album 'Enrique,' establishing him as one of the few artists to dominate both Latin and mainstream charts simultaneously. |
| 2001 | "Hero," from the album 'Escape,' became one of his best-selling singles with 8 million copies sold worldwide and debuted at number one in the UK, cementing his global crossover status. |
| 2010 | "I Like It" featuring Pitbull reached the top five on the Billboard Hot 100, extending his record-setting run on Billboard's Dance charts where he holds more number-ones than any single male artist in the chart's history. |
| 2014 | Released 'Sex and Love,' his tenth studio album, which became his second English-language album to debut at number one on Billboard's Top Latin Albums chart. |
| 2016 | Billboard named him the top male dance club artist of all time and dubbed him The King of Latin Pop, citing his 70 number-one rankings across various Billboard charts. |
| 2021 | Released 'Final (Vol. 1),' his eleventh studio album, announcing it as the first of two farewell albums and his 27th number-one on Billboard's Hot Latin Songs chart. |
| 2023 | Headlined The Trilogy Tour with Ricky Martin and Pitbull, a sold-out 19-date North American arena run produced by Live Nation that marked the first time all three superstars co-headlined together. |
| 2024 | Released 'Final (Vol. 2),' his twelfth and final studio album, featuring collaborations with El Alfa and Belinda, closing a recording career that totaled more than 100 million units sold worldwide. |
| 2024 | Completed the second leg of The Trilogy Tour, an arena run that stretched from Fresno to Tampa and reinforced his standing as the biggest-selling Latin recording artist in history with 154 number-ones across Billboard charts. |