Songs and Stories with Gloria Estefan Reveals A Wit and Talent Unlike Any Other

Despite being a Spanish-language focused website, I have made no secret that my favourite singer of all time is Kelly Clarkson (definitely not a Spanish native speaker, but an impressively fast learner). So, when I found out that Clarkson was going to host a four-part summer series of her talk show’s segment “Songs and Stories”, and that Gloria Estefan was in the roster, it felt like two very separate parts of my world were colliding. And it was a joyful collision. More of this please, NBC! See Estefan and Clarkson duet on Turn The Beat Around.

For those of you unfamiliar with Clarkson’s Songs and Stories, it started off as a segment on her (at the time of writing) 22-time Emmy winning show (yes, I will plug her success, I’m that much of a fan). In the segment Clarkson delves into singers’ back catalogues and the stories behind their hit songs. The segments always include multiple duets that inevitably tend to go viral online.

In the past few years, she has performed with a-listers such as P!nk, Alanis Morisette and Heart. Unsurprisingly, as an American show, the artists who are given such a designated spotlight are English native speakers (who sing in English). That’s why Gloria Estefan’s inclusion in such a select group intrigued me – and this time the show was given a “prime time” slot. While Estefan has many hit songs in English – and Clarkson has demonstrably dedicated a lot of time to learning Spanish (she even has a Spanish duet with Blas Cantó – check it out on Spotify) – I didn’t anticipate their voices blending so seamlessly, in both languages!

Before I delve into the standout moments from the episode, for those unfamiliar with Gloria Estefan and her ground-breaking career, here is a quick overview:

Estefan was born in Havana, Cuba, in 1957. Her family fled to Miami following Fidel Castro’s rise power in 1959, and were among the first wave of Cubans who sought a new life in the United States. Her family continued its connection to the Caribbean island, with her father, José, fighting at the Bay of Pigs, against the Cuban government at the time.

Estefan released her first Spanish-language album, Mi Tierra, in 1993. On Songs and Stories, she revealed that her record label had not been particularly supportive of an entirely Spanish record. Audiences were used to a Spanish-infused sound, she explained, but not the full thing. She went on to stress the importance, both for herself and for Miami Sound Machine, of trying “to salvage [their] sound because when Castro came to power, he took everybody out of the history books who was anti-Castro”. For Estefan, Mi Tierra was not only an identity mission but also a celebration of Cuban music. As she put it, they felt like “cultural ambassadors,” carrying a duty as well as a passion. See Clarkson and Estefan duet on Mi Tierra on NBC's YouTube.

Estefan’s time in the spotlight hasn’t been without hardship. In one of the biggest lucky-escapes of an a-lister of all time, Estefan miraculously survived a near-fatal tour bus crash in 1990. The incident left her with a fractured spine, and the singer was warned her at the time that she might never walk again. Luckily, fate had something else in mind and Estefan recovered against all odds. On Songs and Stories, the Cuban-American legend joked about how painful it was when friends and fans encouraged her to “get up on [her] feet”, one of her biggest songs. To which Clarkson quickly joked that she has the same ironic situation with her chart-topping hit, Stronger (What Doesn’t Kill You) whenever she’s going through a rough moment.

Her anecdotes didn’t stop there. Estefan also revealed that, as a young woman, she was once approached by the CIA because of her language skills and Cuban background. She laughed about it on Songs and Stories, joking that she would have been the “perfect cover” since her career already gave her access to world leaders. See the official clip on NBC's YouTube.

That quip underlines something bigger: the complicated Cuban–American relationship. From the Bay of Pigs to the Cuban Missile Crisis of 1962, the history between the two countries has been fraught for over 60 years. For Cubans in Miami, those memories remain raw, even if they feel like a lifetime ago for outsiders. When I went to Cuba in 2016, it was during Barack Obama’s presidency, when relations were visibly softening. Obama openly made the relationship better, with travel and trade restrictions loosened and a genuine sense that life on the island was opening up.

But under the Trump Administration, things quickly swung back. Not only were many of Obama’s reforms undone, but a new rule was introduced meaning that any non-Americans who had travelled to Cuba after 2020 would now need to apply for a full US visa rather than qualify for the simpler ESTA system. It’s one of those bureaucratic reminders of how politically fraught the relationship still is.

And yet, the reality of it all really hit me at Miami airport in 2023. Ordering a sandwich, I had to switch into Spanish because the cashier couldn’t understand my “British” accent. While I had time to kill in transit, I looked up at the departures board and there were more than 20 flights heading to Havana that very day. Of course, they were for second and third-generation Cubans visiting family, but from an outsider’s perspective it summed up the strange reality. The two countries are separated politically, yet so deeply connected by language, music, and family ties that the divide feels both rigid and porous at the same time.

For me personally, although I first came across Gloria Estefan when Conga was used in an episode of Futurama (don't judge me), her legacy has a habit of popping up in unexpected places. I suppose that is the truest testament to her career. One such moment was when I had the good fortune of seeing the bioplay On Your Feet!, which brought a joyful burst of her music and story to the West End. So I’ll gladly welcome more surprise encounters with Gloria Estefan, as the Songs and Stories collision was nothing short of fantastic.