The 10 Biggest Sycophants from Literature and History

Modern-day D.C. offers up an impressive roster of toadies, but who are the most accomplished bootlickers on record?

We have entered a period of spectacular bowing and scraping, in which White House staff compete publicly in stroking the ego of their flattery-addicted boss. Sucking-up takes a variety of forms, from petty compliment, to cloying flattery, to outright treachery. Our responses are just as varied — from impatience and annoyance to disgust and rage. Sycophancy combines with other vices — hypocrisy, lying, manipulation, and fraud — and intensifies them. The examples of bootlicking below list a few famous historical toadies as well as some books that offer brilliant accounts of sycophancy and its corrosive effects.

History’s Bootlickers

For his combination of all the worst elements of sycophancy, and his persistence in carrying out his program of flattery, Joseph Goebbels, Hitler’s Minister of Propaganda, would deserve first consideration. Goebbels’ propagandizing began with his leader. He initiated the “Heil Hitler” salute and insisted on the use of “Der Führer” as title. His letters are full of groveling praise — such as repeated testimonials that the experience of Hitler transformed his consciousness — and imagined scenes of glorious triumphs against various adversaries in which the Führer stands firm and unshakeable. Almost single-handedly, Goebbels created the prototype for subsequent versions of state-sponsored sycophancy.

The power of the state can also be marshaled in less pervasive demonstrations, as an incident from the Roman Emperor Caligula’s notorious rule reminds us. During an illness early in Caligula’s reign, a commoner vowed to give his own life if the emperor recovered. The man made his vow publicly, hoping through his extravagant offer to show his deep loyalty and to elicit a generous award for his avowal. Although Caligula did recover, the lickspittle’s tactic backfired spectacularly. Once back on his feet, Caligula chose to take the man at his word and ordered his execution. Quite the lesson that words should mean what they say. Death by sycophancy is hard to top.

The former Secretary of State Henry Kissinger showed great promise as sycophant from his earliest days as a graduate student at Harvard’s School of Government, where his fellow students, playing upon the “A” from his middle name, called him “Henry Ass Kissinger.” But in the Nixon administration, Kissinger became a world class sycophant. One need only recall his deplorable comment to Nixon after a meeting with Golda Meir in 1973, then prime minister of Israel. Meir had implored Nixon to ask the Russian government to allow more Soviet Jews to emigrate to avoid persecution. Nixon, intent on détente with the USSR, sought to avoid the request. Kissinger had a ready response: “The emigration of Jews from the Soviet Union is not an objective of American foreign policy. And if they put Jews into gas chambers in the Soviet Union, it is not an American concern. Maybe a humanitarian concern.” Truckling to the boss doesn’t get much uglier than this.

Saint-Simon’ Memoirs records an instance of truly astonishing sycophancy. His gossipy account of the Duke de Vendôme’s insolence includes a description of the duke’s morning routine. Upon rising the duke habitually took up his “chaise-persée” (a portable toilet), upon which he held court and received official visits for hours. Vendôme welcomed one supplicant, a bishop on ambassadorial duty for the Duke of Parma, in his usual style. During the interview, he rose, turned his back to the bishop, and wiped himself. Disgusted, the bishop refused to see him again. However, diplomacy is the art of finding a way. The bishop found the perfect substitute for the peculiar requirements of negotiation with the Duke: the super-serviceable Giulio Alberoni, who had risen from poverty though a series of clerical appointments. Alberoni, treated to the same display by Vendôme, had a ready reply: “O culo d’angelo” (roughly translated, “Oh, ass of an angel!”), and he “ran to kiss” the duke’s behind. His long career within the church and among European courts was assured.

Literature’s Toadies

History give us the spectacle of sycophantic excess, but literature teaches us how to think about it. Plutarch’s “How to tell a Friend from a Flatterer sets out the nature of both the sycophant and the target, and he is unsparing to each. Sycophancy begins in the target’s self-love, which impairs his judgment. Because “everybody is himself his own foremost and greatest flatterer,” that is, complacent and trusting to his virtues, the sycophant need only second and celebrate this flatterer within. The sycophant, on the other hand, has “no nature, no abiding-place of character to dwell in.” He takes the shape of his target’s desires, ultimately leading “a life not of his own choosing but another’s, moulding and adapting himself to suit another.” Plutarch exposes the essential nullity of sycophants and in this essay offers nothing less than a flatterer’s playbook.

Charles Dickens’ David Copperfield provides one of literature’s most repulsive sycophants, the reptilian Uriah Heep. Dickens ensures readers will revile Heep by emphasizing his physical creepiness — he is cadaverous and lanky, with clammy hands and “sleepless eyes.” David feels slimed every time he encounters him. Initially a clerk in the employ of the lawyer Mr. Wickfield, Uriah Heep undermines his employer by weaponizing professions and displays of humility. Schooled in being “umble” by his father, Heep is always quick to affirm his lowly station and abase himself, no more so than when he invites the young David to tea. Working their young guest like a pair of tag-team wrestlers, Heep and his mother use every angle of perverse flattery to corkscrew information out of the boy. Mrs. Heep goes so far as to venture that “If I could have wished father to remain with us for any reason, it would have been that he might have known his company this afternoon.” To wish the return of a husband and parent from the grave to have tea with a twelve-year old boy surely registers high on any list of outrageous flatteries.

Chaplain to the bishop of Barchester, the duplicitous Obadiah Slope in Anthony Trollope’s Barchester Towers, epitomizes the lick up/kick down sycophant — fawning with the powerful, tyrannical with subordinates. In a campaign to become bishop himself, Slope flatters and consoles his way into the circles of the town’s best families and social coteries. Barchester’s “foolish women” readily listen to the twaddle he whispers into their ears, but not Eleanor Harding, one of his intended targets. Initially sympathetic, Eleanor denounces him as “an abominable, horrid, hypocritical man…the most fulsome, fawning, abominable man I ever saw.” Trollope exposes Slope’s every weasel-like move and hypocrisies with a satiric bite that makes this novel an irresistible read.

Lauren Weisberger’s The Devil Wears Prada explores the self-loathing endured by sycophants. Everyone who works at the fashion magazine Runway sucks up to its abusive editor, Miranda Priestly. The novel humorously exposes the sycophantic world that envelopes Miranda, who requires and ruthlessly enforces outrageous displays of ingratiation. Runway’s staff, fashion designers, restaurant owners all grovel before the diabolical Miranda. Here the “devil” seems to mete out just punishment for those willing to debase themselves in pursuit of some vacuous conception of access or success. The protagonist’s crushing humiliation is a perplexing act of self-nullification.

While the bargain struck by the sycophant — fleeting moments of vain gratification — often seems a losing proposition, the arrangement can at times have some advantage. In The Line of Beauty, Alan Hollinghurst presents a virtuoso suck- up in Nick Guest, a well-educated hanger-on in a rising conservative MP’s home. Hollinghurst brilliantly links Nick’s aesthetic sensibility to his abilities as a flatterer. Early in the novel Nick accompanies the family of a friend as they drive to a country estate. But while the family can be bored as they contemplate the visit, Nick is essentially on duty as resident sycophant. From the outside, one would be uncertain of Nick’s intentions. But upon arrival, Nick revels in the pleasures of an intense connoisseurship, tracing the beautiful surfaces of the estate, noting the details of its elegance and its rich evocation of architectural traditions. Nick is a flunkey but this seems the price of the ticket to the world of the rich and powerful. He savors the view, but he also relishes his intense response to it: Nick understands and enjoys what the family owns better than they do.

But for power of execution and depth of treatment, one must conclude with Shakespeare’s masterful account of weaponized sycophancy — his Othello. The play provides a catalog of strategies for ingratiation, subversion, and destruction, as Iago corrupts the mind of the noble Othello. No play shows the devastating personal consequences of sycophancy, or its intricate ties to other vices so starkly. The sycophant is capable of every fraud, every hypocrisy, every deceit. And no work of art evokes the mystery of sycophancy — its springs and sources in the character and life of the ingratiatory — so completely.

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