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"La Isla Bonita" is a song by American singer Madonna from her third studio album True Blue (1986). Written and produced by Madonna and Patrick Leonard, with additional lyrics by Bruce Gaitsch, the song was originally presented by Leonard as an instrumental demo to Michael Jackson, who turned it down; Leonard then played it to Madonna, who liked it and wrote the lyrics and melodies. "La Isla Bonita" was Madonna's first song with Latin influences; its instrumentation features Cuban drums, Spanish guitar arrangements, maracas and harmonicas. The lyrics talk about an island named San Pedro; according to Madonna, the song is a tribute to the beauty of Latinos. The song was released as the fifth and final single from True Blue on February 25, 1987. It was included on her compilation albums The Immaculate Collection (1990), and Celebration (2009).
Upon its release, "La Isla Bonita" was positively received by music critics who, in retrospective reviews, have considered it one of Madonna's best songs. It was also commercially successful, becoming her 11th top five hit on the Billboard Hot 100 and second Adult Contemporary number one; it topped the charts across several countries in Europe, including the United Kingdom, where it became her fourth number one. In the accompanying music video, Madonna portrays two opposite characters: a Catholic young woman, and a flamenco dancer; academics applauded the clip for using Hispanic fashion and symbology as icons of beauty and romanticism. The song has been performed in seven of Madonna's concert tours, the last being 2019–2020's Madame X Tour, and covered by multiple artists, including Ricky Martin and Alizée.
The music video for "La Isla Bonita" was directed by Mary Lambert, who had previously worked with Madonna in the videos for "Borderline" and "Like a Virgin" (1984). Filming took place in downtown Los Angeles in March 1987, and lasted four days; over 500 extras of Hispanic descent, including a then-unknown Benicio Del Toro, who was paid $150, participated in the shooting. According to Sharon Oreck, in her book, Video Slut (2010), it was a very simple shooting. In the visual, Madonna plays two characters: a short-haired Catholic woman and a "flamboyant" flamenco dancer. As the flamenco dancer, she is dressed in a voluminous red Andalusian-style dress; for the shy, pious Catholic character, she dons a simple white dress.
The video starts as several Latin people dance in a Spanish barrio while Madonna, as the Catholic woman, watches them from her window; she sheds tears in her room and reluctantly ignores their invitation to join them. At one point, she's shown using a rosary to pray, bowing before an altar full of Catholic imagery. The "passionate" flamenco dancer Madonna dances inside a bright red room with red candles, candelabra and, towards the end, leaves to join the dancers in the streets. "La Isla Bonita" had its world premiere on MTV on March 6, 1987, and became the most requested video in the channel's history for a record-breaking 20 consecutive weeks. In Europe, it was the most heavily rotated clip on television.
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