Timecapsule: 23 years of ''La Isla Bonita'' single

"La Isla Bonita" was released as the fifth and final single from Madonna's third studio album, ''True Blue'', on February 25, 1987 and achieved worldwide popularity, topping charts in the United Kingdom, Germany, France, Belgium and reaching number four on the United States Billboard Hot 100 chart.

"La Isla Bonita" was written by Patrick Leonard and Bruce Gaitsch. The song was previously written as a lament for the mythical Spanish island called San Pedro and was offered to Michael Jackson for his ''Bad'' album, who, according to Gaitsch, turned it down. While working with Leonard on the ''True Blue'' album, Madonna accepted it in Jackson's place and re-wrote the song's lyrics, thus earning herself a co-writing credit. The song was the first Madonna song to employ Spanish motifs, going so far as to include Spanish lyrics. The Spanish theme would reoccur throughout her career, manifesting itself in lyrics for "Who's That Girl", "Spanish Eyes", "I'm Going Bananas", the Spanish version of "You'll See" called "Verás", "Be Careful" which was a duet with Ricky Martin, "Sorry", "Lo Que Siente La Mujer" - the version in Spanish for her song "What It Feels Like for a Girl," and "Spanish Lesson" on the ''Hard Candy'' album.

The song is written in the key of C♯ minor and is set in the time signature of common time like most pop songs, moving at a moderate tempo of 95 beats per minute. Madonna's vocal range spans two octaves, from G₃ to C₅. The phrase "La Isla Bonita" translates as "The Beautiful Island" in English. The title and first line of the song refer to an island called San Pedro, held by some to be Ambergris Caye in Belize, as the song may also mention the principal village there called San Pedro Town. However, Gaitsch has mentioned that at that time, Madonna was spending time in an U.S. town of the same name, and both Madonna and her then husband Sean Penn were good friends with a poet called San Pedro and novelist Charles Bukowski. Madonna herself has not clarified this in any interview. Instead, she referred the song as being a tribute to Latin America and its people, along with an island and to herself.

''La Isla Bonita" debuted at number fifty-six and reached a peak of number four on the Billboard Hot 100 chart in March 1987. The song was Madonna's second number one single on the adult contemporary chart, following 1986's "Live to Tell". It became the eleventh consecutive top-five hit for Madonna, a feat surpassed only by the Beatles and Elvis, which later Madonna surpassed with her 2008 single "4 Minutes". The single also found success on the Hot Dance Singles Sales chart, where it peaked at number one.

"La Isla Bonita" was a worldwide hit, reaching No.1 in various countries, including the United Kingdom, Canada, France and Germany. In Canada, the song debuted at number seventy-four for the issue dated April 4, 1987 and reached the top of the chart in its tenth week on the issue dated June 6, 1987, remaining on the chart for twenty-five weeks. The song topped the UK Singles Chart for two weeks. The single was certified silver by the British Phonographic Industry (BPI) for sales of 250,000. "La Isla Bonita" was Madonna's first number one song in France, where it spent three weeks at the top spot in July 1987. In Europe, it became her fourth number one hit from ''True Blue'', topping the Eurochart Hot 100 for three weeks in 1987. The song also peaked atop the charts in Switzerland, Belgium and Austria along with reaching the top-five in Ireland, Italy, Netherlands, Norway and Sweden.

The music video was set in Los Angeles and was directed by Mary Lambert, who directed a number of Madonna's 1980s videos, including those for "Borderline" and "Like a Prayer". The Latinos in the video are portrayed as stereotypes as people with no care in the world, unemployed adults, school deprived children and a crumbling barrio. However, the music video was critically appreciated for its utilization of Hispanic fashion as an icon of beauty and romanticism. Collen McDanell, in his book ''Material Christianity'', noted Madonna's use of Catholic objects in the video like the candlestands and home shrines, thereby giving them a new meaning according to her own. Author Douglas Kellner noted, "such 'multiculturalism' and her culturally transgressive moves turned out to be highly successful moves that endeared her to large and varied youth audiences". Madonna's Spanish look in the video became popular and appeared in the fashion trends at that time in the form of boleros and layered skirts accessorizing with rosary beads and crucifix like the video.

Madonna has performed "La Isla Bonita" on most of her world tours including the 1987 ''Who's That Girl World Tour'', the 1993 ''Girlie Show World Tour'', the 2001 ''Drowned World Tour'', the 2006 ''Confessions Tour'', and in the ''Sticky & Sweet Tour'' in 2008–09. She also sang it at the 2007 ''Live Earth'' benefit concert in London.