The Far Side is infamous for its ability to surprise, and even shock its readers – with some of Gary Larson's comics no less than certifiably jaw-dropping in their use of death, mayhem, and discomfort to a comedic end. Though this kind of "edgy" humor is in vogue now, Larson's pioneering dark humor was, in its heyday, both challenging, and even at times controversial.

Despite its reputation, The Far Side was never caustic in its depictions of murder, torture, arson, and other such macabre human activities; that is, Gary Larson never set out to hurt his readers by exposing them to its brand of darkness – but what he did want to do was routinely catch them off guard.

If anything, Larson's attitude toward the bleaker aspects of life can be described as flippant, but even still, this came from a positive place, as The Far Side's creator sought to transmute tragedy into comedy, and frequently succeeded.

10 A Hit Gone Wrong Leads To Collateral Damage, Far Side Style

First Published: December 21, 1994

This is one of the final Far Side comics ever published, as Gary Larson officially retired from cartooning after January 1, 1995. In the , a uniformed police officer yanks a dog by its leash, hauling it off on a one-way trip to the pound, as a detective explains to a shocked widow that her husband "was just in the wrong place at the wrong time," and was inadvertently steamrolled alongside the family cat, who was the canine's real target.

It is hard to argue against this being a perfect Far Side cartoon, one which is funny at the conceptual level, and perfectly executed in both illustration and caption; the sublimely mixes the macabre and the absurd, blending the real and the surreal in Gary Larson's often imitated, but never replicated style. As a further exploration of Larson's more shocking comics shows, not every one of his jokes needed to achieve this pristine balance between elements, but those that did rank among his greatest successes.

9 Gary Larson Delivers A Public Service Announcement, Far Side Style

First Published: July 10, 1992

This is high on the list of the darkest Far Side comics, but it is also one of Gary Larson's most overt pieces of social commentary, with the 's image of vans selling guns, "hanging ropes," and cigarettes boiling down to one simple, but potent point: smoking kills. It is perhaps The Far Side's harshest truth in its history – yet fans of Larson will recognize that it is stems from a strong sense of empathy.

Larson's work is notable for finding balance between different diametrically opposed elements: gravity and levity, real and surreal, the mundane and the absurd, to cite just a few examples. That said, this comic can arguably be described as imbalanced; it skews darker than many Far Side comics, but it also contains richer, clearer subtext than most – making it unique among Larson's significant ouvre.

8 God's Wrath Enters The Digital Age, As The Far Side Shares Its Dark Theological Perspective

First Published: September 17, 1991

God appeared frequently in Far Side comics, as Gary Larson made it clear that he wasn't afraid to engage in some lighthearted idolatry. However, this stands out as especially memorable, and strikes many readers as particularly noteworthy, because of the way it shows God actively taking the life of one of The Far Side's human characters – by smashing the "smite" button on his desktop computer and dropping a piano on the man's head.

Reading deeper into this joke, readers can consider the significance of depicting the Almighty as cruel and capricious, and while the joke might not seem all that contentious by today's standards, at the time of its publication it almost certainly caused a stir in at least a few particularly pious households. Most often, what makes a Far Side comic "jawdropping" is a mix of Gary Larson's desire to upend readers' expectations and the biases readers themselves bring to reading his work.

7 There's Nothing Funny About Gun Violence – And That's The Point Of This Far Side Comic

First Published: June 10, 1991

In another one of The Far Side's cartoons which comes down heavier on the dark side of the spectrum, Gary Larson tackles the heavy subject of gun violence – by depicting a clown thinking "laugh at me, will they," as he stands at the counter of "Bob's Guns," trying to decide which firearm to buy. Though the contains a relevant social message, the surface level subject matter will strike some readers as off-putting, or otherwise wholly inappropriate.

The implication of the joke, of course, is where its true darkness lies, while its humor comes from the clash of imagery in the : clown, clad in suspenders and a green-and-black polka dot shirt, against the stark gray aesthetic of the gun store, along with the slumped shoulders and pursed lips of the man behind the counter. Again, though, this darker Far Side comic is paired with one of its most blatant messages – that anyone who thinks a gun is going to solve their problems is a bozo.

6 Gary Larson Revels In The Glory Of A Great Garage Sale Score, Far Side Style

First Published: February 12, 1988

Gary Larson frequently used babies in Far Side punchlines, if for no other reason than it was an effective shortcut to getting a rise out of his readers. As a result, babies starred in some of the most absurd Far Side cartoons, including this one, which led to more than one outraged letter to newspaper editors across the country.

Here, a man shows his friend the baby in a bottle over the mantle of his fireplace, marveling that he "got the whole thing at a yard sale for five bucks." While the imagery is goofy, as was the standard for The Far Side, the concept of the joke proved visceral enough to upset some people, for whom even an overtly cartoonish artistic style could not diffuse the discomfort caused by the idea once it entered their minds.

5 Gary Larson Highlights How In Some Arguments, Once A Line Is Crossed, There's No Going Back

First Published: September 21, 1983

On the opposite side of the light-dark divide, this cartoon is closer to a prototypical Far Side, in that it is unquestionably laugh-out-loud funny, but with its humor underwritten by a healthy dose of horror. In the , two technicians take a petty workplace squabble into a restricted part of the building – by tearing holes in each other's hazmat suits in a "radioactive era," potentially dooming them both.

In addition to a perfectly framed visual, this Far Side comic exemplifies Gary Larson's characteristic blend of over-the-top humor with dire implications. The action of the joke is absurd, but the setting makes it dangerous, and in turn readers will find themselves gasping, either in shock, or from laughing too hard.

4 This Far Side Snake & Its Man Squeeze Were Meant To Make Readers Slightly Uncomfortable

First Published: March 21, 1983

In this Far Side snake cartoon, a serpent its that, "it's true, Barbara...you're the first woman I've ever brought here," back to its lair under a rock, which the human woman in question is shown improbably squeezed into. Aside from the icky implications of an interspecies romance, what makes this Far Side particularly evocative is the feeling of claustrophobia it evokes.

That is, the way Barbara is drawn as being head first into an enclosed underground space, with seemingly no room to maneuver out, or to move at all, nor much air to breath, will be a trigger for some readers who can't stand the thought of confined spaces. This is integral to the functionality of the joke, but it is also certain to leave many readers aghast.

3 The Reason Songbirds Are An Endangered Species On The Far Side

First Published: December 23, 1986

This Far Side cartoon eschews the use of a caption, and it doesn't need one; the rifle clutched in the human character's hands, and the scowl on his face, as his pet songbird quotes "hey boid!...Shaddup!" in between bursts of melodic chirping, tell the reader everything they need to know about what is about to happen here, and the implication is unquestionably jawdropping.

What is striking about the darkness of this Far Side comic is the resolute calmness with which the man in the armchair polishes his gun – note also the small detail that he is strapped with a pistol in a shoulder holster, while his hands are occupied with what looks to be an automatic rifle – as he prepares not just to kill his pet, but to completely overkill it. Yet this is also key to the bleak hilarity of the , emphasizing the fact that, in Far Side comics such as this one Gary Larson's creative choices were often designed to serve more than one purpose, deliberately creating a desired set of contradictory feelings.

2 This Early Far Side Comic Features The Comic's Most Hilarious Itchy Trigger Finger

First Published: November 10, 1980

Talk about an all-time "oops" moment – in this comic from the first year of the Far Side, a man accidentally blows away his dinner guests with a shotgun, which his wife attributes to his overconsumption of caffeine. In 1980, The Far Side was still limited to a limited number of newspapers, and a small pool of readers – and over the next several years, Gary Larson's comic would ascend in popularity thanks to its ability to shock readers, while still leaving them wanting more.

In that sense, this is an arch-example of the kind of Far Side comic that helped shape its success, as well as continuing to define Larson's legacy to this day. To a large degree, the most memorable Far Side cartoons are those to which the reader responds with "I can't believe he drew that," and this comic resolutely embodies that.

1 The Far Side Never Truly Wanted To Torture Its Readers, Just Tickle Them

First Published: October 14, 1980

The Far Side was repeatedly criticized over the years for its jokes set in dungeons, depicting torturers and torture victims. As with all of Gary Larson's work, these s were deliberately hyperbolic, and overly cartoonish, and complaints about them are largely a result of taking the artist's work way, way too seriously.

Nevertheless, as with all of The Far Side's most controversial, most jawdropping installments, this reaction – or overreaction – stemmed from encountering something wholly unexpected in the newspaper funny pages. This comic, for example, in which a black-hooded torturer tours his proud parents around his workplace, helped to make a name for Larson in the comic industry, for better or worse. In that sense, it is essential to understand this comic in order to develop a greater understanding of The Far Side's overall impact in the medium.