There are many reasons Columbo stands out from the pack of detective series’, not least due to its cart-before-horse approach: revealing the killer within the first ten minutes, before following Peter Falk’s lieutenant as he pokes and prods for clues. However, one of the most interesting aspects of Columbo is the space it affords its villains. Despite the qualities of wealth, privilege and arrogance being typical character traits, there are a handful of peculiarities which make the killer as endearing and complex as Lieutenant Columbo himself.

Without a doubt, Columbo was a game-changer for the detective genre not only in terms of reversing the typical whodunit structure, but putting the spotlight on a conveyor belt of antagonists, each operating within the series’ framework, but with unique motivations and varying degrees of remorse. Portraying Columbo as a consciously befuddled, avuncular, and grubby detective allowed for an array of slick, complex, and beautifully-realized secondary characters to make their mark in each of the sixty-nine episodes.

Jack Cassidy: The Ultimate Bad Guy

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No Columbo-phile could neglect the three-time villain, Jack Cassidy (father of David) in their Best Of lists. Appearing as the primary antagonist in "Murder By The Book," "Publish or Perish," and "Now You See Him," Cassidy is the bad guy we love to hate. Ostensibly playing the same character in each episode - all slippery charm, arrogance and wealth, the Falk versus Cassidy dynamic is classic cat-and-mouse with a whiff of class warfare. He might not bring the greatest acting range to his appearances, but the crisp charisma makes him a thoroughly engaging baddie.

Ruth Gordon: Age Shall Not Weary Them

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Playing famous and feisty crime novelist Abigail Mitchell in "Try and Catch Me Now," 80-year-old Oscar winner Ruth Gordon goes head-to-head against Columbo, having locked her niece’s widow in an airtight safe in the belief that he is responsible for her death. An understandable motive; however, the joy in Gordon’s portrayal is found in her ever-growing affection for the man tasked with uncovering her secret, as well as her mimicking of his infamous “just one more thing” catchphrase. Having revealed the depth of her sadness at losing her niece, Columbo acknowledges the injustices she has suffered, prompting her to admit a growing attachment to his presence: “I'm beginning to be very fond of you, Lieutenant. I think you're a very kind man.” But the love-in can’t last long, as Columbo warns her not to count on his good nature when it comes to matters of law and order.

Chitty Chitty BANG BANG!

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From wide-eyed chimney sweep to down-trodden Pulitzer Prize-winning killer, Dick Van Dyke has a varied career and "Negative Reaction" allows everyone’s favorite fake-cockney a chance to present as one of the more sympathetic villains in the Columbo franchise. Under the thumb of an antagonizing wife with a fetish for belittling him, Van Dyke ensures a conflicted audience, disapproving of murder, but feeling a deep hatred towards such his loathsome spouse. In fact, it barely takes one scene to find oneself screaming “knock her off, Bert!” But as with many Columbo murders, the attempt at securing freedom is far too elaborate, with the killer’s plan including the purchase a second property, fake telephone conversations in front of a housekeeper, and the icing on the cake, a self-inflicted gunshot wound to the leg.

It’s Been A Pleasance, Donald.

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In "Any Old Port In A Storm," Donald Pleasence plays a character we may generously describe as ‘antisocial.’ Uninterested in anything barring wine, the character of Adrian Carsini is oblivious to the yearning of his lovesick secretary, devoid of friends, and goes through life in an utterly joyless fashion without the slightest emotion for anything outside the realm of expensive grapes. Upon hearing the news that his half-brother is ready to sell his share of the only thing which brings him a facial expression, the family winery, Carsini has no qualms about knocking him off under the pretense of a scuba diving accident, before merrily booking a first class flight to receive his Wine Society’s Man of the Year award. Despite his awkward and socially unaware personality, there appears to be a mutual respect between Columbo and the killer, a sense that in another life they could be friends, as shown in the lieutenant's final gesture: a shared bottle of wine before carting him off to prison.

Janet Leigh: Killer In A Catsuit

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She may have perished in Alfred Hitchcock’s Psycho, but in "Forgotten Lady," Janet Leigh is the murderer. Leigh plays Grace Wheeler, an increasingly irrelevant celebrity of yesteryear hellbent on a second shot at stardom. When her elderly husband refuses to finance her latest project, Wheeler decides he is more than a problematic party pooper, and must be taken out of the equation. Naive and energetic, Leigh’s portrayal of an aging actress is a thing of beauty, as she stares transfixed at reruns of her old films, jumping at any opportunity to step back into the spotlight. But there is something amiss in Wheeler, from the way she flips from scaling trees in a skintight catsuit in order to assassinate her husband, to a confused, sincerely blanked-out child. It is the cause of this discrepancy which becomes the most tragic reveal of all, and prompts Columbo to do the unthinkable: let her off the hook.

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Man In Black Seeks Lady For Sunday School

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With a career built on religion, redemption and sorrow, Johnny Cash seems a strange choice to play a materialistic, sex-obsessed gospel singer. Perhaps this disparity in his public persona versus the requirements of the role accounts for the incongruous about-face at the end of "Swan Song;" however, before the episode retracts the entire premise, Cash proves himself more than capable. In the role of Tommy Brown, a singer who has amassed legions of young and eager female fans through his biblical songs and teachings, Cash seems to be living his best life, however a dark secret (and BOY is it dark) sees the character suffocating under the control of his dogmatic wife (yup, the old ‘domineering woman’ chestnut) and relegated to the role of performing monkey, unable to engage in the fruits of rock stardom, namely bedding young women and buying flashy cars. What’s the solution? Why, a light plane crash of course! Sure, Tommy must endure a broken leg, but bones heal faster than an emasculated ego…

William Shatner Does William Shatner

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In "Fade In To Murder" William Shatner plays television detective Ward Fowler (great name, shit bloke) who is being blackmailed by a studio exec, handing over a portion of his lucrative earnings in bid to keep his army desertion under wraps. But enough is enough for our oddly-syntaxed friend, as he dons a costume from the wardrobe department, fiddles with a VCR to assure the perfect alibi, and heads to the local deli to dispose of his enemy with all the finesse of an elephant doing origami. Clumsiness aside, the joy from this episode comes from Columbo's enlisting of Fowler's 'as-an-actor-I-have-access-to-the-thoughts-and-emotions-of-everyone' powers to help him get into the mindset of the killer, as well as the genuine affection the two seem to hold for one another. It's fun, it's silly, and there are enough wink-and-a-nudge lines to satisfy the hardcore fans.