آلبوم Enrique سال 1999

: "Enrique" album

By 1999, Iglesias had begun a successful crossover career into the English language music market. Thanks to other successful crossover acts, most notably that of Ricky Martin, Latino artists and music had a great surge in popularity in mainstream music. Iglesias' contribution to the soundtrack of Will Smith's movie Wild Wild West, "Bailamos" became a number one hit single.
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After the success of "Bailamos", several mainstream record labels were eager to sign Enrique. Signing a multi-album deal after weeks of negotiations with Interscope, Iglesias recorded and released his first full CD in English, Enrique. The pop album, with some Latin influences, took two months to complete and contained a duet with Whitney Houston called "Could I Have This Kiss Forever" and a cover of the Bruce Springsteen song "Sad Eyes". The album's second single, "Be with You", became his second number one.
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The final single from the album was the song "You're My #1", re-recorded and released in selected territories as a duet with local acts - Alsou in Russia, Sandy & Junior in Brazil and Valen Hsu in Asia.

آلبوم Vivir سال 1997

: "Vivir" album

In 1997, Iglesias' star continued to rise with the release of Vivir (To Live), which put him up with other English language music superstars in sales for that year. The album also included a cover version of the Yazoo song "Only You", translated into Spanish as "Solo en Tí".

Insisting on playing large arenas and stadiums, that summer, Enrique, backed by sidemen for Elton John, Bruce Springsteen and Billy Joel, played to sold-out audiences in sixteen countries. Beginning the tour in Odessa, Texas the tour went on to three consecutive nights in Mexico's Plaza de Toros and two at the Estadio River Plate in Argentina to over a hundred and thirty thousand people as well as nineteen arenas in the U.S. The tour is considered by many to be the biggest tour by a non-English speaking act of that time.

Three singles released from Vivir, "Enamorado por Primera Vez", "Solo en Tí" and "Miente" topped the Latin singles chart as well as those in several Spanish-speaking countries. Along with his father and Luis Miguel, Iglesias was nominated for an American Music Award in the first-ever awarded category of Favorite Latin Artist. It was said beforehand that the elder Iglesias would walk out if he did not win the award. Iglesias lost out to his father this time, but did perform the song "Lluvia Cae" at the event