Enrique Iglesias

In many ways, you could consider this Madrid transplant a Latin pop pioneer. He was one of the first Spanish-language artists to play for arena-size audiences in the United States (a feat accomplished during his 1997 Vivir tour) without the support of a crossover hit. In addition, his 2002 video for "Quizás" was the first Spanish-language tune played on MTV's Total Request Live and the first song of its kind to be performed on The Tonight Show with Jay Leno. This opened doors for Latin artists such as Juanés, Shakira, and Uruguay's Jorge Drexler to have their non-English material promoted on major TV networks.

At age 33, Iglesias has comfortably settled into superstar status. As a songwriter, he has successfully placed tunes in the hands of Clay Aiken, Melanie C., and others, and in the meantime has acted in small roles on TV shows and in films. And what remains one of Iglesias's greatest qualities is his ability to not take himself too seriously. Just see the video for "Do You Know? (The Ping Pong Song)," wherein he sits patiently as a zany director explains his concept for the clip, which has his muse meeting a tragic demise ("Love lost, it's the future," the Scorcese wannabe says at the end). Or see the TV sitcom How I Met Your Mother, in which he appears as a massage therapist named Gael, who also happens to be an Iglesias look-alike. On his current tour, he is plugging two separate compilations of his Spanish and English hits (the latter slated for release later this year); predictably, they include several previously unreleased songs.