"The Last of the Famous International Playboys" was the third single released by Morrissey. The song was not featured on one of Morrissey's main studio albums, but can be found on the compilation album Bona Drag along with the B-side "Lucky Lisp". The artwork for the single features Morrissey, aged 7, up a tree in Chorlton-on-Medlock, Manchester — literally a boy at play. "The Last of the Famous International Playboys" is notable for featuring three of Morrissey's former colleagues in The Smiths — Andy Rourke, Mike Joyce and one time former Smiths rhythm guitarist Craig Gannon — all of whom also appear on the B-side, "Lucky Lisp".
The song mythologizes, somewhat ironically, the notorious pair of vicious London gangsters known as the Kray twins (Ronnie and Reggie Kray), who held a tight rein on the East End of London during the 1960s with a network of protection rackets and other criminal enterprises, whilst maintaining public respect through legal businesses and charity events. They were eventually sent to prison for life for fatally shooting rival gangster, George Cornell, at the Blind Beggar pub in Whitechapel in March 1966, and then fatally stabbing another rival, Jack "The Hat" McVitie, in the basement of a house in Hackney in October of that same year.
A few years after its original release and Top Ten UK chart appearance in 1989, "The Last of the Famous International Playboys" was brought into the public limelight again when Morrissey was reported to have sent a wreath to Ronnie Kray's funeral in 1995.
The title and lyrics of "The Last of the Famous International Playboys" also seem to allude to John Millington Synge's 1907 play, The Playboy of the Western World, which is about a group of rustic townsfolk in the county Mayo in western Ireland who become enthralled with an eloquent, charismatic young man named Christy Mahon, who freely boasts of killing his tyrannical father and then fleeing the British authorities now after him. The locals at Michael Flaherty's tavern celebrate Christy's exploits, and one of them, Sara Tansey, offers a toast to him, naively valorizing his purported crime by conflating it with the broader spirit of rebellion against the British colonial establishment in Ireland: "Drink a health to the wonders of the western world, the pirates, preachers, poteen-makers, with the jobbing jockies; parching peelers, and the juries fill their stomachs selling judgments of the English law."
However, when Christy's father shows up very much alive, the townsfolk realize that Christy has been telling tall tales and they shun him as a liar and a coward. Christy tries to redeem himself by actually murdering the old man right before their eyes, and they come to understand that the ugly, brutal, dishonorable reality of criminality and violence often differs starkly from its romanticizing in tale and legend. Old Mahon improbably survives his son's vicious attempt on his life, and thus Christy escapes a hanging by the townsfolk; the two of them eventually leave the town. As the daughter of the tavern keeper, Peegan Mike, observes "...the blow of a loy, have taught me that there's a great gap between a gallous story and a dirty deed." Peegan later regrets having become disillusioned with Christy and for not having married him when she had the chance, saying to herself "Oh my grief, I've lost him surely. I've lost the only Playboy of the Western World".
Morrissey's lines in the "The Last of the Famous International Playboys" — "Oh, I never wanted to kill,/I am not naturally evil./Such things I do/Just to make myself more attractive to you./Have I failed?" — seem directly inspired, with a touch of irony, by the action and themes of Synge's play as related to the fashionable media mythologizing of the Kray twins and their exploits since the 1960s.
