Morrissey's lyrics were inspired by gangster brothers the Kray Twins, notorious in London's East End during the 1960s, whom he believed to be an example of the media glamourizing violent criminals.

Street wrote the music, which took influence from the post-punk group the Fall and an introduction similar to that of "The Man Who Sold the World" by David Bowie.

Upon release, the single became another commercial hit for Morrissey, reaching number six in the UK despite initially mixed reviews.

[3] Morrissey explained that he wanted to explore the way that the tabloid press made celebrities out of violent criminals in the song, saying that the Krays "exemplify" the "way notorious people can be quite glamorous.

[4]"The Last of the Famous International Playboys" and follow-up single "Interesting Drug" are notable for featuring three of Morrissey's former colleagues in the Smiths: bassist Andy Rourke, drummer Mike Joyce rhythm guitarist Craig Gannon.

"[2] Morrissey said in a 1989 interview that he had high hopes for the single: "'The Last Of Famous International Playboys', is the first record that I feel hysterical about.

"[8] Morrissey first performed the song live at his infamous debut solo concert at Wolverhampton's Civic Hall in December 1988, alongside Rourke, Joyce, and Gannon.

[9] That same month, The Guardian described the show as "primarily a showcase for Morrissey's New Year single, 'The Last of the Famous International Playboys.

NME initially gave the single a negative review, with Stuart Maconie saying the track was "'Panic' without the magnetism and the blinding self-confidence" and concluding "I would still chain myself to a disused railway line in Bacup for him, but the lad can do better"[11]—in a review for Bona Drag one year later, however, Maconie expressed a change of heart, writing, "At the time of its release, I was rather mealy-mouthed about 'Playboys' so let me take this chance of saying I was wrong about this sterling tune full of stomping boot boy romanticism.

In a retrospective review, Ned Raggett of AllMusic was much more favorable, writing "Morrissey's performance is grand and passionate".

Spin named it Morrissey's seventh best solo song, writing "Unusually wiggy guitar effects add to the unseemly drama.

"[15] Clash included it in its unranked list of the seven best Morrissey solo singles, writing "A love letter to London's notorious Kray twins, it's playful, hilarious and supremely confident.

It stars the actor Jason Rush, who had appeared in the 1987 television drama Two of Us,[4] intercut with footage of the band performing against a green-screen backdrop.

In the video, Rush is portrayed as the song's "dear hero imprisoned" in his metaphorical jail of a bedroom with walls decorated with posters of male icons such as Elvis Presley, Jack Nicholson, and George Best.