The music video, directed by James Foley, shows the singer in a more demure, toned-down appearance, inspired by actresses such as Grace Kelly, intercut with clips from At Close Range.

The song's performance on 2006's Confessions Tour caused controversy, as it had the singer hanging from a mirrored cross simulating a crucifixion; religious groups condemned the number as an act of hostility toward the Roman Catholic Church.

[2] They met at a barbecue in his house, where he showed her a song he'd created in his studio called "Love Makes the World Go Round", that Madonna then sang at the Philadelphia Live Aid benefit concert on July 13.

[6] After Madonna heard Paramount had turned down the track, she decided to use it as the end credit song in a movie that Penn was working on, titled At Close Range.

[2][7] She recalled: "Sometimes when I'm writing songs, I'm just channeling [...] [The lyrics are] kind of inspired by [At Close Range] and family secrets and the things that make you who you are, but you don't necessarily want to share".

[2] Music writer Dave Marsh held that the song speaks about "the complexity of deceit and mistrust", while according to Allen Metz and Carol Benson ―authors of The Madonna Companion: Two Decades of Commentary― and Boston.com's Scott Kearnan, it is about "childhood scars" and "bearing the burden of some enigmatic secret and coping with a painful past", which may or may not involve abuse.

[29][30][31] "Throughout her career, Madonna has occasionally reasserted herself as an artist by releasing a dramatic ballad that proves that behind all of the contrived controversy and manipulation, she's a genuinely talented singer.

[11] "Live to Tell" was acclaimed by the Record-Journal's Jim Zebora, who gave True Blue an overall negative review: "[An] absolutely marvelous [song] [...] [with an] enchanting melody and arrangement, [and] captivating lyric[s]".

[35] According to The New York Times' Stephen Holden, "['Live to Tell'] proves that vocally Madonna isn't limited to catchy novelties and disco tunes – she can carry off a weightier ballad".

[36] In this vein, Allen Metz and Carol Benson felt the "compelling" track "expanded" Madonna's musical horizons, noting that she sings with "moving conviction".

[37] In The Complete Guide to the Music of Madonna, Rikky Rooksby said it was True Blue's second "strongest track" after "Papa Don't Preach", and compared it to "Luka" (1987) by Suzanne Vega.

[41] James Croot from New Zealand website Stuff opined "Live to Tell" is a "heart-rending and haunting ballad that Madonna tried to recapture a few times later in her career ('This Used to Be My Playground', 'Take a Bow') without exactly the same kind of impact".

[44] Scott Kearnan named "Live to Tell" Madonna 21st best single and wrote: "With 'Crazy for You', [she] proved she could nail a hit ballad: for teenage girls to slow dance to at prom.

[16] Billboard's Andrew Unterberger, and Entertainment Weekly's Chuck Arnold, placed it at number 18 and 17 of their rankings, respectively; the former named it "the first truly great Madonna ballad", while according to the latter, it found her "displaying greater depth and maturity than ever before.

[14] On Slant Magazine's ranking, it was allocated on the fifth spot: "Madonna’s first and, arguably, most dramatic reinvention was scored by this spare and haunting ballad [...] [It] features one of [her] richest vocal performances", wrote Sal Cinquemani.

[25][68][27][69] In France, the single reached the chart's sixth position, and was certified silver by the Syndicat National de l'Édition Phonographique for shipment of 250,000 copies.

[71] Inspired by the "glamorous" style of the Golden Age of Hollywood and figures like Brigitte Bardot, Grace Kelly and Marilyn Monroe, the singer decided to tone down her appearance; "I got sick of wearing tons of jewelry – I wanted to clean myself off", she explained.

[73][72] In Your Neighbor's Hymnal: What Popular Music Teaches Us about Faith, Hope, and Love, Jeffrey F. Keuss wrote: "[T]here is something in that loneliness [from the video] that makes it feel like the most authentic thing [Madonna] has ever done", comparing the shots of her singing alone to Carl Theodor Dreyer's 1928 film The Passion of Joan of Arc, and the cover artwork for Sinéad O'Connor's second studio album, I Do Not Want What I Haven't Got (1990).

[74] According to Jeremy G. Butler, author of Television: Critical Methods and Applications, through her singing, Madonna appears to speak to Penn's character, addressing his problems directly like the chorus of a classical tragedy.

On the first one, she sang the song standing motionless in a single spotlight, dressed in a black ensemble with tassels, golden tips and ribbing, designed by Marlene Stewart.

[76][77] Writing for the Los Angeles Times, Robert Hilburn noted that the artist sang "with a delicate, embracing feeling that few of even her biggest fans would have imagined possible five years ago".

[79][80] On the Blond Ambition World Tour, "Live to Tell" was performed in a medley with "Oh Father" (1989) and given a Catholic theme: The stage was set up to resemble a candlelit cathedral, while Madonna wore black vestments.

[81][82][83] She sang knelt down in a prie-dieu, in front of a stained glass cathedral window that was lowered from the ceiling; dancer Carlton Wilborn played a priest Madonna interacted with during the number.

[91] While the staff of the Boston Herald singled out Madonna's "authoritative and impassioned" vocals, Leslie Gray Streeter from The Palm Beach Post said that the "preachy" performance "slowed [the concert] down in an unsatisfying way".

[96] Wearing a necklace of Swarovski crystals shaped like teardrops, Madonna sings the track from atop a box that flies over the audience as images of people who died of HIV/AIDS ―including Keith Haring, Herb Ritts, and Freddie Mercury― are projected on drop-down screens throughout the venue.

[97] Rolling Stone's Kory Grow compared the number to an awards ceremony's in memoriam segment, while Kate Solomon from British newspaper i deemed it "one of the most moving pop performances [I've] ever seen".

[100][96] On December 2, 2024, in memory of World AIDS Day, Madonna uploaded a montage fan-made and official video clip of the performance on her YouTube channel.

[101] The Russian Orthodox Church and the Federation of Jewish Communities of Russia (FJCR) described the number as amoral, and urged the public not to attend the concert in the country.

[104] By contrast, a pastor from North Denver defended the "powerful and very reverent performance", which "calls the world to take notice that there are 12 million children who are currently orphaned"; he also applauded Madonna for "trying to wake us up to [...] care for those who are most often forgotten".

[105] Madonna herself stood by the number, claiming that Jesus wouldn't be mad at "the message I'm trying to send", and released a statement: I am very grateful that my show was so well received all over the world.