Music Career From 1999–2001: Enrique and Escape

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 and Gloria Estefan, Latino artists and music had a great surge in popularity in mainstream music. After attending one of his concerts in March 1999, Will Smith asked Iglesias to contribute to the soundtrack of his movie Wild Wild West. His contribution "Bailamos" was released as a single and became a number one hit in the US.

After the success of "Bailamos", several mainstream record labels were eager to sign Iglesias. 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. It contained the song "Rhythm Divine", a duet with Whitney Houston entitled "Could I Have This Kiss Forever", and a cover of the Bruce Springsteen song "Sad Eyes".

In 2000, Iglesias performed at the Super Bowl XXXIV halftime show alongside Christina Aguilera, Phil Collins, and Toni Braxton. Shock jock Howard Stern repeatedly played a tape of a supposedly very off-key Iglesias on his radio show and accused the Iglesias of not being able to sing live. On June 8, 2000, Iglesias sang the song live on Stern's show with just a guitar accompanying him. After the performance, Stern remarked, "I respect you for coming in here; you really can sing". Iglesias would remark that the controversy was the best promotion he could have. The album's single "Be With You" became Iglesias's second number one single on Billboard's Hot 100.

In 2001 Iglesias released his second English language album Escape. Where most of the Latin crossover acts of the previous year experienced some difficulty matching the record sales of their first English language albums, Iglesias actually went on to sell even more. The album's first single, "Hero", became a number one hit in the United Kingdom, and in many other countries. The entire album was co-written by Iglesias.

Escape is his biggest commercial success to date. The singles "Escape" and "Don't Turn Off The Lights" became radio staples, faring well and placing highly or topping various charts both in North America and elsewhere. A second edition of the album was released internationally and contained a new version of one of Iglesias's favorite tracks, "Maybe", as well as a duet with Lionel Richie called "To Love a Woman".

Iglesias capitalized on the album's success with his "One-Night Stand World Tour" consisting of 50 sold-out shows in 16 countries. Including Radio City Music Hall and three consecutive nights in London's Royal Albert Hall, the tour ended with a big show at Stadium National Lia Manoliu in Bucharest, Romania. The concert launched MTV Romania, with the video for "Love to See You Cry" being the first to be shown on the channel.

The second leg of the tour, "Don't Turn Off The Lights", was completed in the summer of 2002, with two sold-out nights in Madison Square Garden and another two in Mexico's National Auditorium. The tour finished with a single show in the Roberto Clemente Coliseum in San Juan, Puerto Rico.