Ricky Martin Remembers His Historic Grammy Performance, Getting Love From Madonna

On Feb. 11 at 5:30 p.m. PT/8:30 p.m. ET, Yahoo Live will live stream Ricky Martin's concert from the Gramercy in New York City. Tune in HERE to watch!

Delivering a show-stopping performance at the Grammy Awards isn't easy. There's tremendous pressure to wow an audience of musical peers, industry heavyweights, and, of course, millions of home viewers. But Ricky Martin defied expectations and accomplished this feat with his breakout performance at the 1999 Grammys, which is now widely considered to be one of the best in Grammy history. That one performance helped catapult him to household-name status in the U.S., and he went on to sell millions of albums around the world.

At the time, the Puerto Rican singer had yet to totally shake off his image as a former boy-band star in Menudo and catch the attention of mainstream American audiences. But his now-legendary Grammy performance changed all that.  

"I will always be incredibly thankful to the Grammys for letting me perform that night," Martin tells Yahoo Music. "There was definitely a before and after."

Singing his hit tune "The Cup of Life" (which was the official song of the 1998 FIFA World Cup), backed by a brass band and accompanied by circus performers, Martin confidently swayed his hips, busted out some salsa moves, flashed an irresistible grin, and exuded such charisma that his star quality was undeniable.  

Grammy telecast viewers and music superstars alike stood up and took notice. Madonna even famously ambushed him backstage to congratulate him on his performance. "Madonna showed up in my press conference that night," recalls Martin. "I already knew her — I'd met her years before that. She's always been extremely kind and very respectful. When she walked onstage at the press conference, I was like, 'Yeah, hey hey, what a moment!"

Madonna wasn't the only music icon to express her adoration and applaud Martin. "After that night, I was receiving phone calls from people who were my idols," Martin says. "I was pleasantly shocked by their reactions… the next day I received phone calls from Luciano Pavarotti and from Sting — people I always respected."

The timing couldn't have been better, and soon after his Grammy Awards performance, Martin released his 1999 self-titled album, which featured his breakout hit "Livin' La Vida Loca." and went on to become one of the best-selling albums in pop music history, shifting 22 million copies worldwide.