| 1989 | Founded in Miami by Raul Malo and Paul Deakin as a defiant outlier in a local scene dominated by hair metal and punk, the band's Cuban-inflected grooves and Bakersfield twang caught the ear of super-producer Tony Brown, who signed them to MCA Nashville. |
| 1994 | Broke through commercially with 'What a Crying Shame,' their MCA Nashville album that went platinum in the US and earned the ACM Award for Top New Vocal Duet or Group, establishing them as one of country music's most unpredictable and thrilling live acts. |
| 1995 | Won the CMA Award for Vocal Group of the Year, with 'What a Crying Shame' simultaneously certified platinum, a rare double recognition that cemented their status as chart forces and award-circuit fixtures. |
| 1995 | 'Here Comes the Rain,' from 'Music for All Occasions,' won the Grammy Award for Best Country Performance by a Duo or Group with Vocal at the 38th Grammy Awards, validating the band's blend of Cuban grooves and Bakersfield-inspired twang with music's highest honor. |
| 2013 | Returned from a nine-year hiatus with 'In Time,' a full-scale comeback that frontman Raul Malo described as finding 'a brand new purpose, not just to go out and play for tickets and do the oldies,' reintroducing the band to both longtime fans and a new generation. |
| 2015 | Released 'Mono,' further deepening their Latin and pop palette and providing the refreshed, unmatched stage show that earned the band renewed praise as one of the finest live acts in the business. |
| 2020 | Released 'En Español,' their first all-Spanish-language album, which reached a career-best #6 on Billboard's Folk chart and underscored the Cuban roots at the heart of Malo's voice and songwriting. |
| 2024 | Released 'Moon & Stars' via Mono Mundo, their thirteenth studio album, then joined Dwight Yoakam on the Cosmic Roundup and Rodeo Tour, bringing the album to arenas and amphitheaters across the US. |
| 2025 | Raul Malo disclosed a Stage 4 colon cancer diagnosis that had progressed to leptomeningeal disease, forcing the cancellation of most tour dates; bandmates honored his legacy with a sold-out tribute show at the Ryman Auditorium, Nashville's most storied country venue. |
| 2025 | Malo passed away at age 60, closing one of country music's most singular careers, a golden-voiced maestro whose Cuban-Miami upbringing permanently bent the boundaries of the genre. |