Enrique Iglesias' Emotional Life: The Billboard Cover Story

David Needleman
Enrique Iglesias photographed by David Needleman for Billboard

No topic is off limits as the singer opens up about that strained relationship with Dad, Anna Kournikova, the recent death of his dog, and the pressure to keep building his empire.

It's a rare occasion that Enrique Iglesias is actually at the offices of his Mr. 305 Productions in Miami's Bay Point neighborhood. So rare, in fact, that Iglesias' own corner office serves as a storage room for his longtime manager Fernando Giaccardi, financial manager Juan Carlos Sanchez and tour manager Abel Tabuyo, with suitcases and boxes everywhere. The one personal touch? Piles of awards and platinum plaques. "I keep this stuff here so it stays out of my house," says Iglesias.

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His presence here is all the more impressive when you consider the rough day he has been having. "I haven't slept in two days - I really haven't," says Iglesias. Not only is he fighting fatigue from a red-eye flight from London, he also has spent a good chunk of his morning crying. Lucas, his German shepherd of 12 years, died just as Iglesias was arriving back home from his weeklong promotional trip in Europe. It's the saddest he has been since, well, 2010 - when another beloved dog, Grammy, died just as his album Euphoria had been released. "It's funny that this is happening again when an album's coming out. It's a circle of life thing, right?" says Iglesias, who also owns a third dog, Jack.

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Most stars would have postponed or canceled an interview during such a moment of personal duress. But the 38-year-old is energized, engaged and eager to talk for the next two hours about the many lessons learned from a decorated career that has spanned half his life. Such is a typical day for a guy whose career began in Spanish with his self-titled 1995 debut and has gone on to log 24 No. 1s on Billboard's Hot Latin Songs chart (a record, more than any other artist), two Billboard Hot 100 chart-toppers and 10 albums - the latest of which, the bilingual Sex and Love, is the occasion for his current global trek.

Iglesias is back home in Miami for the day, but in just 24 hours, he'll be on another plane to Curaçao to shoot on-air interstitials for German cable network RTL. Shortly thereafter, he's off to Barbados to film similar material for a Canadian radio station. ("You can tell the coldest countries are just dying for summertime," he says of the destinations.) Interestingly enough for a guy with such a well-worn passport, Miami is the only place he calls home or owns property. "People ask me where I go on vacation, and I tell them, 'Miami, hanging out with my dogs.'" But, he adds, "If I buy a castle in Spain, you're more than invited."

Relentless globe-trotting has been par for the course ever since Universal Music Group chairman/CEO Lucian Grainge gave Iglesias some important advice in 2001, when Grainge was head of Polydor in the United Kingdom. "No matter how much technology advances, you can't expect fans to feel close to you if you don't go visit them," Iglesias recalls Grainge saying. "If you're going to France, make sure you do French TV, French radio. You have to be in their environment. If you just put records out and stay home, it doesn't work."

Most recently, that has meant a whirlwind two-week period in March that saw stops in Mexico, Germany, Los Angeles, Cuba and the Dominican Republic. Different stops focused on different singles from Sex and Love, with Iglesias singing the romantic ballad "El Perdedor" (The Loser) - featuring fellow Latin-pop superstar Marco Antonio Solis - on a big soap-opera awards show in Mexico, and the next day flying to London to perform the U.K. top 10 dance-pop hit "I'm a Freak" (featuring fellow Latin-pop crossover star Pitbull) on the U.K. edition of The Voice.

"The Enrique business is a seven-day-a-week, 24/7 venture," says Republic executive vp Charlie Walk, who dubs Iglesias "one of the most hands-on artists I know." Iglesias knows how to work his sex appeal, but he also knows how to work his demographics. He studies the charts cover to cover each week and takes an active role in the A&R process of all his records. That entrepreneurial spirit was first identified by Jimmy Iovine, who signed Iglesias to his major-label deal at Interscope, beating out offers from Warner Music and Clive Davis at Sony that would have netted him an additional $10 million or more. And in the past four years with Republic, Iglesias has further carved out his own global take on Latin pop with the staying power and track record that can unquestionably stand up to his superstar father, Julio.

Iglesias is the third eldest of Julio's eight children, but was raised primarily by a nanny, Elvira Olivares, shortly after Julio and Enrique's mother, Isabel Preysler, divorced. Though Enrique has a famous father, his ambition was self-contained, and supported not by his family but by Olivares, who paid for his first demo. "I never really shared [my music] with anyone. I felt like it wouldn't happen and I would have too many people with their opinions," he says. "By the time I was 17, 18, I was quietly flying to Mexico to sign my first deal and going to school to work with a musician, Roberto Morales, who liked the same Bruce Springsteen and Phil Collins records I loved, and I could learn from his chord progressions."

Though Iglesias remains close with the majority of his family (including older sister Chabeli Iglesias and two half-sisters from his mother's second marriage) who often come to his concerts and visit him in Miami or Spain, the subject of his father is a complicated one. "There are people who say, 'Do you think you would be in music if your dad was not a singer?' If I were to bet on it, maybe not," says Enrique. But Julio has little involvement in his son's career or personal life. In fact, Julio had given an interview a few days prior in which he mentioned having never met Anna Kournikova, 32, the former tennis star who has been Enrique's girlfriend for 12 years. The story made international headlines, and Enrique not only confirms that it's true, he launches into a lengthy explanation. "People say, 'Yeah, 10 years, 12 years, that's a long time not to see your father,'" he says, noting that he and Julio Sr. have in fact seen each other on several occasions without Kournikova in the past decade. "But the last 14 years, 15 years of my life have flown by. And that's the only way I can truly explain it. There's no reason why - it's not his fault, and it's not my fault."

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If Iglesias is evasive on the topic of his father, perhaps it's because he doesn't know where his own family life is heading. When it comes to marriage to Kournikova, he's in no rush. "She doesn't bug me at all," he says. "Our mentality in that way is a little different." And on having children, "Why not? I don't know. I don't know if I will ever be ready, but yes, I would at some point. You never know, I could be 70 years old when that happens."

He and Julio are both still global touring artists, which could make schedules tricky, and explain why Julio has only seen his son at occasions like funerals. "Yeah, but is that really an excuse?" says Enrique frankly. "Let's be honest. All I know is that if my dad ever needed me, I would be there first thing. When I was a child growing up, if I ever needed my dad I knew he would be there for me. So as long as I have that for me, that's fine."

Still, he seems to have inherited his father's stubbornness to succeed. Though Iglesias had a hugely successful, decade-long run with Interscope - during which "Bailamos" and "Be With You" topped the Hot 100 and Iglesias sold more than 5.4 million albums in the United States, according to Nielsen SoundScan - he wasn't afraid to walk away from that partnership in 2010, when he and the label couldn't see eye to eye on "I Like It," his collaboration with Pitbull. The track was originally cut in 2007 with rapper T.I., and earmarked for Iglesias' 2008 greatest-hits set before Interscope passed. "They saw it as a one-listen record," says an executive with knowledge of the label's response. But Iglesias saw its potential. "There are songs that you're willing to bet your career on. If they don't have that vision or they don't feel it, it's tough," he says.

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He quickly shuffled over to Universal sister label Republic, under the guidance of then-president Monte Lipman, and turned "I Like It" into his biggest hit since 2001's "Hero," peaking at No. 4 on the Hot 100 (with the promotional aid of MTV's Jersey Shore soundtrack) and spurring renewed interest in his 2010 album Euphoria, which was repackaged in 2011 with "Tonight (I'm Loving You)," another double-platinum hit that also went to No. 4. A freshly minted status as a dance-pop divo has earned Iglesias a lesser-known distinction as the solo male artist with the most No. 1s on Billboard's dance chart (beating out Michael Jackson and Prince), and helped fuel two global tours - his 2011 Euphoria Tour, which grossed $30.8 million, and a 2012 co-headlining tour with Jennifer Lopez, which banked $21.1 million in ticket receipts, according to Billboard Boxscore.

Even more change was afoot last December, when Iglesias and Giaccardi (his manager since 2000, having previously worked with Iglesias as a promotion executive at his first independent label, Fonovisa) left management firm The Collective to join Red Light Management as head honcho Coran Capshaw's first major Latin signing. He's now part of a roster that includes a range of acts from Dave Matthews Band and Tim McGraw, to EDM heavyweights Tiesto and Pretty Lights, to R&B stars Alicia Keys and Miguel. Eventually, Giaccardi says, they'll be called upon to bring in other acts as well as expertise in branding and marketing to the Latin audience.

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Which is why Iglesias laughs when people chide him for taking four years to put together Sex and Love. Not only was Euphoria a two-and-a-half-year album cycle, he says, but he recorded more than enough material to fill out two albums this time around. The resulting release could be the subject of a seminar on the modern, global album: Different packages targeted different audiences. There are four versions of Sex and Love in the marketplace with additional songs in both English and Spanish, on iTunes, internationally and at both Target and Walmart. (You know you have a serious wealth of material when duets with global stars like Kylie Minogue and Jennifer Lopez are relegated to bonus tracks.) And there are alternate versions of the singles for different formats - including Latin pop and tropical, as "El Perdedor" was serviced with pop and bachata remixes, while the lush "Loco" has Iglesias duetting with two different acts for those formats, Romeo Santos and India Martinez, respectively.

Up next is a global launch of single "Bailando," originally cut for Sex and Love in Spanish with newcomers Descemer Bueno and Gente De Zona. The song was recently rerecorded with a bilingual mix for the United States and Europe featuring a guest rap from Sean Paul. If the title is reminiscent of his breakout hit "Bailamos" (We Dance), well, that's the point - "Bailando" translates to "Rhythmic Dancing" in Spanish, and its street-wise reggaeton sound is carefully accessible enough to reach four formats at once, as "Bailamos" did when it became his first Hot 100 chart-topper in 1999. (Giaccardi jokes that a trilogy could be in the works: "In 10 years, he'll have to make 'Baile' - 'I Danced.' ")

Sex and Love debuted somewhat quietly at No. 8 on the Billboard 200, with sales of 24,000 copies, then slipped to No. 42 in its second week. But Iglesias and his camp have the long view - it took 18 months for Euphoria to churn out two top five singles. "I've never been so focused on the first week. For me, it's about getting to the finish line," says Iglesias. Adds Walk, "It's a continuous process to drive the brand accordingly, globally, and in the U.S. We've continued to be fully committed to get this music not just to his core but to a younger audience."

If Republic seems newly incentivized to make Sex and Love work in the States (it has yet to chart a single in the upper half of the Hot 100), that's no coincidence. Iglesias' contract with Universal is essentially up after he turns in one more greatest-hits compilation, and he's quietly exploring options with other partners. "As a matter of practice, we don't divulge artist contract details publicly," Lipman tells Billboard. "We cherish our deep relationship with Enrique Iglesias, and we intend to continue our partnership for a long time."

Iglesias has withstood the Latin-pop boom of the turn of the century with a dedicated work ethic and a fine-tuned ear for a hit. That was enough to make his Euphoria comeback in 2011 his biggest-earning year in nearly a decade, when he ranked No. 23 on Billboard's Money Makers list (out-earning the likes of Usher, Justin Bieber and Kanye West), pocketing more than $7.3 million from recorded music and touring.

And he's still working on the art of being able to say "no." In recent years, he has turned down multimillion-dollar deals to appear as a judge on American Idol, The X Factor and the original cast of NBC's The Voice. The X Factor and The Voice both would have interfered with his 2012 touring schedule. And Idol, which would have given him the spot previously held by Lopez for the 2013 season, arrived at a time when he was in the early stages of Sex and Love. "I cared more about going into the studio and writing songs," he says. "That's what makes me happier."

This can be a point of frustration for Giaccardi, who nevertheless understands the longer game at stake that will ensure Iglesias a third decade of success. "We've passed on things that didn't make sense," he says, "or that Enrique was not feeling and they would come out shitty." But Giaccardi also knows that Iglesias has 44 million Facebook fans and 8 million Twitter followers. Pitbull has touted similar stats successfully to marketers like Bud Light, Dr Pepper, Playboy and Voli Vodka. "This is the time to start reaping the benefit of so many years on the brand," says Giaccardi.

Iglesias is keenly aware of the many deals being thrown at his Latin-pop peers currently, especially as measured ad spend on Spanish-language media in the United States reached an all-time high in 2013 to $7.1 billion, a 2.3% increase over 2012, according to Kantar Media. Still, he's hesitant. "Every time I think about my career with dollar signs, I've made mistakes," he says. "And every time I've thought less about money, the more money I've made."

Iglesias has even stayed out of the wildly popular World Cup anthem market, turning down an offer from a "big, big brand." That was a difficult "no," he says, "because I'm extremely passionate about [it]. But if I'm going to do a big promotional tour, I got to love the song." The campaign's anthem in question wouldn't have allowed him to put much of a stamp on a prerecorded track, he notes. "It's still got to feel like me."

Still, Iglesias is flexing his business muscles these days, inking branding deals that have an equity or royalty component to them. He's frequently spotted, as he is today in Miami, rocking a vintage-looking ball cap brandishing the logo for Atlantico, the super-premium rum in which he became one of five co-owners in 2011 (making his stake in the company as much as 20%).

What started from a tiny retail and restaurant footprint in Florida and the Dominican Republic in 2008 quickly grew to a tripling in sales among the "control states" (roughly 33% of the U.S. market) during Iglesias' first two years of involvement in 2012 and 2013, according to Beverage Information Group analyst Adam Rogers. The spirit is now available in 20 global territories. It's still a long way off from the kind of revenue Sean "Diddy" Combs pulls in from his equity partnership with Diageo's Ciroc vodka (an estimated $100 million annually), but it's the type of deal that keeps Iglesias incentivized in a way the typical commercial plug never could.

Then there's Adrenaline, his fragrance line for Coty debuting later this summer. Though the scent took three years to develop, Iglesias says he always knew what the name would be - even before the ingredients were finalized. In fact, he briefly entertained naming Sex and Love after the product. "I have a very tough time cross-promoting things. Because there comes a point where you sell so many products, which one do you believe in?"

Two decades as a global pop star doesn't come without its wear and tear, however. Iglesias complains of migraines "that are killer," and hangovers that take days to recover from when they used to take hours in his 20s. He has become less of a gym rat now that the rigors of touring have become their own cardio. "The first two weeks of touring are tough on me because I notice it in my bones, in my joints, it's 'Whoa,'" he says. "But my doctor says I'm crazy because I never even stretched or anything. I was always very athletic as a kid, but I know the day will come when I have to warm up and stretch."

But it's this moment, that quest for the next top 10 global smash, that seems to keep Iglesias motivated. He stands up on the couch to revisit the Hot 100 chart that's hanging on the wall from the week "Bailamos" first topped the tally in September 1999, and marvels at all the artists in the top 10 who have stood the test of time (Christina Aguilera, Santana) and those who, well, haven't (Chris Gaines, Garth Brooks' short-lived alter ego; 702; Sugar Ray). "There's always some artists who don't need to fight, that get immediately played on top 40 no matter what - you know you have a guaranteed top 20 hit," he says, assessing his place in the landscape. "I got to fight like it's my first record every time."