In June 2000, radio personality Howard Stern received a tape of a supposedly off-key MP3 of Iglesias singing, along to the track "Rhythm Divine". Stern played this humorous clip throughout the week on his radio show insinuating that Iglesias lip synched and couldn't sing well outside the studio, even suggesting that Iglesias himself did not sing on his albums, comparing him to Milli Vanilli. Iglesias flew straight in to New York to appear on Stern's show, singing acoustic versions of "Rhythm Divine" and "Be with You", after which Stern told Iglesias he had silenced his critics. Iglesias would go on to say that controversy and his appearance on the show was the best promotion he could have.

In 2002, Enrique began filming the music video for his single "Escape". While filming, he would meet his long time companion and significant other, Russian tennis player Anna Kournikova. Many reports started showing up in 2007 of them splitting, and in 2008, after Enrique making a publicity