By the turn of the millennium, he had made a successful crossover into the mainstream market and signed a multi-album deal with Universal Music Group for US million with Universal Music Latino to release his Spanish albums and Interscope Records to release English albums.
In 2010, he parted with Interscope Records and signed with another Universal Music Group label Republic Records to release bilingual albums.
His generous act is partly down to his well-known charm and good humour, but it may also stem from another enchanting night at The Palm, a celebrity hotspot where he could have indulged in succulent Nova Scotia lobster and prime double cut New York strip steak.
But after his comments made headlines he added: 'We are extremely happy the way we are.
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And on Friday evening tennis ace Anna Kournikova, 35, made it clear she has no intentions of fleeing her long-time relationship with Enrique Iglesias, 41, as the two shared tender moments while leaving The Palm restaurant in Beverly Hills.
I don't think it's going to..us any happier."Enrique, 38, met Kournikova, 32, when the athlete appeared in his 2001 "Escape" music video.
"She was just the coolest girl in the world to me," the Latin pop star recalls.
The Moscow-born beauty, who famously appeared on the cover of the Sports Illustrated Swimsuit Issue in 2004, wore a sheer white blouse, which gave the faintest hint of the black bra that lurked beneath.
Anna Kournikova and Enrique Iglesias were spotted enjoying a date night in Beverley Hills this week looking super cute and super stylish!