A dance-pop song that takes influence from Motown and girl groups from the 1950s and 60s, its lyrics address Madonna's feelings for her then-husband Sean Penn.

James Foley directed the official one that aired internationally, which shows Madonna in a 1950s-inspired blue setting, joined by backup singers.

In early 1985, Madonna began dating actor Sean Penn, whom she met in the set of the music video for her single "Material Girl".

[4][7] Composed alongside Bray, the title track was described as Madonna's "unabashed valentine" for Penn, and influenced by the "direct antecedents" of her sound: Motown, girl groups from the 1960s such as the Shirelles, and songs like "Chapel of Love" (1964) by the Dixie Cups.

[13] Personnel working on the song included Bray on drums and keyboard arrangement, alongside Fred Zarr; Bruce Gaitsch played guitar while background vocals were provided by Siedah Garrett and Edie Lehmann.

[17] The "verse-and-chorus" composition is similar to that of "Chapel of Love", with Garrett and Lehman accompanying the singer's convincing "girly" vocals like a choir.

[29] "True Blue" has not been included in any of Madonna's major compilations, but was part of The Holiday Collection ―a four track EP released exclusively in the United Kingdom in August 1991.

By all reasonable measures, it should be disposable pop fluff; but in Madonna's hands, it's an impossibly charming slice of puppy love — albeit a naive one".

[32] Matthew Rettenmund, author of Encyclopedia Madonnica, hailed it a "sweet tune" that features the singer "at her chirpiest and most flirtatious", and "best illustrates [the album]'s ―and Madonna's― dedication to Penn".

[19] AllMusic's Stewart Mason opined the singer's vocals resembled Cyndi Lauper's, albeit "with a slightly less kitschy attitude".

Mark Elliott referred to "True Blue" as the most "representative" of the parent album's nine songs, and an "irresistibly catchy homage" to the 1950s and 60s.

[35] For the Chicago Tribune, Jan DeKnock also praised its girl group influence, and described the song as a "charming [...] perfect end-of-summer confection that will do equally well with pop and adult contemporary listeners".

[36] James Croot from New Zealand website Stuff said it was the "crowning glory" of the parent album; "[a] toe-tapping 1950s-inspired ditty [...] pop-song confection perfection.

[37] For Los Angeles Times' Robert Hilburn, "['True Blue'] mixes the innocence of '50s R&B, with the punch of Spector's '60s classics for a contemporary blend of 'In the Still of the Night' and 'Be My Baby'".

[22][42] Even though he named it "dated and simplistic", Terry Hearn from The Metropolist concluded that, "hearing this [song] from the woman who was singing 'Like a Virgin' could be disorienting, but what a feat it is to shock people by being so simple and pure.

[61][62] "True Blue" was certified gold by the British Phonographic Industry (BPI) on October 10, 1986, and has sold over 557,000 copies as of March 2015.

[65] In Australia, the song reached the chart's top-five and was given a platinum certification by the Australian Recording Industry Association (ARIA) for the shipment of 70,000 copies.

[28] The official music video for "True Blue" was directed by James Foley, with whom Madonna had worked on "Live to Tell" and "Papa Don't Preach", and aired outside of the United States.

[74] Upon release, the staff of British magazine Record Mirror compared the video's aesthetic to that of American television series Happy Days, and said it was as "cute as a choc bar commercial".

[75] Mark Elliott noted that, following the controversy "Papa Don't Preach" and its video had caused, "True Blue" was "nothing [that would] worry the parents, which was probably something of a relief to record company executives".

[68][80] Fans were called on to make and submit their own video for "True Blue, and the winner would be awarded a trip to MTV's New York studios, and granted a check for $25,000 by Madonna herself.

[82] In Gender Politics and MTV: Voicing the Difference, author Lisa A. Lewis wrote that although many featured Madonna wannabes and a wide range of concepts, they all focused on the song's theme of true love.

[81] There were some, however, that dealt with other themes such as power: One had schoolgirls owerpowering and tying up a teacher who spoke ill of Madonna; in another, an American girl and a Russian boy grow up to become president of the United States and of the USSR, respectively.

[82] Aired as the official "True Blue" video in the United States, Gracia and Guest's entry spent weeks in high rotation on the network's Dial MTV countdown program.

[88][89] On the Rebel Heart Tour, the song was re-worked in an acoustic doo-wop style, with Madonna playing the ukelele from atop a tire stack.

[93] The performance of the song at the March 19–20, 2016 shows in Sydney's Allphones Arena was recorded and released on the artist's fifth live album, Rebel Heart Tour (2017).

[98] This rendition was critically appreciated, with Stereogum's Scott Lapatine placing it at number 16 of his ranking of "The 20 Best Indie Rock Madonna Covers".

[99] Australian singers James Blundell and Tania Kernaghan recorded "True Blue" for the former's twelfth studio album Campfire (2017).

[100] Finally, in 2023, Australian singer Darren Hayes did a mashup of "True Blue" and Savage Garden's "I Knew I Loved You" (1999) on his Do You Remember?