The most unexpected Gloria Estefan fan isn’t the millennial with “Conga” and “Rhythm Is Gonna Get You” in her music library or even Deepak Chopra, who follows the Latin singer on Twitter. But it might be the 94-year-old man she met a few hours before we sat down for this interview.
It had been a week of 5 a.m. wakeup calls doing non-stop press for The Standards, Estefan’s latest album, and by the end of it, even the heavy anticipation of the holiday weekend ahead had nothing against this woman’s stamina. After all, this is an album Estefan’s been waiting almost 30 years to record. “At the beginning of your career, who cares about hearing you sing standards if they don’t know who the hell you are?” Estefan says. “It’s not like I’m a crooner like Harry Connick Jr. or even Bublé. That’s not who we were. We loved dance music; we loved everything we’ve done every step of the way.”
Miami Sound Machine in 1984, Estefan in 1991
But the most meaningful songs in Estefan’s life have always been the classics—like her wedding song, “El Dia Me Quieras,” a 1920s tango by Carlos Gardel, and Dinah Washington’s “What A Difference a Day Makes,” the first song she ever sang professionally with Miami Latin Boys (before they became Miami Sound Machine, above) on October 25, 1975, at the DuPont Plaza Hotel—and the “dream was to one day be able to do my take, my version of these songs.” With help from jazz pianist Shelly Berg, Estefan covered 17 personal favorites (narrowed down from a list of 1,000 titles), and her version of “Good Morning Heartache,” the opening track, caught the attention of its original writer, Ervin Drake.
In an email sent to Estefan’s PR agency, the songwriter asked to meet her in New York. “He wanted to say how much he loved the version I did and enjoyed it even more than the Billie Holiday version,” she says. With Berg on the piano, Estefan performed the song for Drake and his 91-year-old wife, the subject of the song. “He had been madly in love with her,” Estefan says. “She was a showgirl and got around town, he said, and had too much fun and broke his heart. And he wrote that song because she’d left him really, really destroyed. He said that he only had eyes for her. And then years later, both their spouses died within a year of each other, and they got back together and have been married 35 years.”
Estefan and husband Emilio at the American Music Awards in 2012
It’s the same amount of time she’s been married to her husband, Emilio Estefan—and their story will get its own creative outlet on the Broadway stage (the musical is currently casting the parts of a young Gloria and Emilio). “We actually have such a beautifully comfortable relationship,” Estefan says. “We’ve been through most of the turmoil that you’re ever going to be through. I’m not the jealous type, and Emilio isn’t really either, but crazy things go on, especially in the middle of this career. Now we can really settle back and do what we want to do. We are deeply in love with each other, and we laugh at everything.” Surely that’s the anti-aging secret?
Estefan tells me she knows why Drake’s alive at 94: “He’s funny—he’s happy and healthy and very, very raunchy!” But beyond getting to serenade someone from that era, the adulation behind Drake’s request is of the highest praise to Estefan, who turned 56 just days before they met. “There’s something in your head when you’re writing a song that you want to hear when somebody performs it,” she says, having three decades of songwriting experience to her own name. “So it’s really a huge compliment, and I was beside myself. They told me that the song made their year. He made my year, I told him.”
We ask Gloria Estefan to comment on a few of her most striking and memorable looks during her career. Click through the gallery to see what she had to say.