10 Comedians We Aren’t Meant to Find Funny


Maybe I will do a list of this kind every month. Or maybe I won’t. I probably won’t. I hope you didn’t like that introductory paragraph very much, because I’m going to write another one:

Comedy is difficult. Making people laugh is the easy part…making people laugh for the right reasons, at the right times, satisfyingly and consistently, is practically a science. For that reason, we come to expect that not every comedian will make it big, and that not every joke they tell will make us laugh. We know that an impressive hit rate is difficult to maintain, and we adjust our expectations accordingly, striking a balance between how much we’d like to be entertained, and how much we can reasonably expect of a fellow flawed human being.

But, sometimes, a particular comedian is doomed from the start. He is not only incapable of making us laugh, but he’s without control over his material, his audience, or even his demeanor. It’s tragic when this happens, and painfully awkward. The floundering comedian is an effective and offputting archetype, and that’s why writers have dipped into this well repeatedly, crafting characters fated to bomb every time, doomed to botch every punchline, making us laugh not warmly, but defensively, and with discomfort.

In the interesting cases of these comedians, laughing at their material means you missed the joke. Here are 10 examples of that irony personified.

1) Fozzie Bear (The Muppet Show)

There’s perhaps no better cultural touchpoint for the ill-equipped comedian than Fozzie Bear, and his signature “wocka wocka” has wormed its way into our vernacular as well, becoming rightfully associated with sub-par material and limp gags. Fozzie’s routine was dated before he was born, relying on simple puns and vaudeville showmanship to generate rapturous laughter and applause that never comes. He’s also, however, eminently sympathetic, which is not only why we like him, but why Kermit keeps him around, and gives him another chance every week to die on stage. With two old curmudgeons heckling him from the balcony above, we are free from the desire to criticize his act, and can instead turn our attention to the uplifting fact that no matter how poorly he’s received, Fozzie’s always devoted enough to his craft to throw away what doesn’t work — in his case, everything — and write a whole new act from scratch. We’d love to see Dane Cook follow his lead.

2) Jimmy Valmer (South Park)

Jimmy Valmer is a special case, in several senses of the word. For one, he’s an 8-year-old boy, which means — unlike Fozzie and everyone else on this list — he isn’t disappointed that he hasn’t made it further in his comedy career. After all, that’s still to come! But he also suffers from several obvious physical handicaps. No matter; Jimmy wants only to make the world laugh, an ambition that’s downright touching by South Park standards, and one made all the more unfortunate by his chronic stutter, which causes him to step on his own punchlines and prevents him from honing his delivery…or even intelligibility. His jokes are about what you would expect from an 8-year-old boy — meaning his material is about as mature as could reasonably be expected and therefore, again, elevates him above the other entries on this list — but they actually seem to work. Stan, Kyle, Cartman, Kenny and the rest of the boys accept him relatively happily for who he is, functioning just fine within their social circle, and he’s not defined in their eyes by his handicaps. No, instead Jimmy is treated exactly as poorly as they treat anyone else. That’s the healing power of humor.

3) Randy (Funny People)

Aziz Ansari is a genuinely gifted comic, and as Parks and Recreation demonstrates weekly, he’s also a talented actor. Both of those things allowed him to bring to life Randy, a pitch-perfect exaggeration — though only just — of a comedian so manic and animated that it completely masks the dire quality of the material he’s delivering. The greatest stand-up comics raised their volume for emphasis. Those from Randy’s school of performing, on the other hand, do it to drown out audience thought, keeping them cheaply engaged and laughing hollowly so that they won’t realize there isn’t any substance. Funny People is just one of many movies that Ansari steals wholesale from their ostensible stars, and the character of Randy has gone on to a have a full life outside the film: Ansari deploys him during his actual stand-up routines now, perhaps as a point of comparison to his normal material, but more likely as a cathartic blow against more popular, more profitable contemporaries of his, who cash larger paychecks but don’t have anything worth saying. Randy may be a popular draw within the world of the film, but all he really does is pull audiences away from more deserving performers.

4) Kenny Bania (Seinfeld)

In contrast to Randy, Kenny Bania is a hack we actually tend to like. Like Fozzie Bear before him, we feel protective of Kenny Bania, as though we don’t trust that he’ll survive the cruel world of stand-up comedy. Even the typically staid Jerry breaks down his personal barriers and takes Bania under his wing — however temporarily. Bania is overjoyed by the simplest, laziest pieces of observational humor, often interrupting his mentor with a sincere and irony-free exclamation of “That’s gold, Jerry! Gold!” His perpetual enthusiasm and sunniness is a rare thing for the Seinfeld gang, and it’s no wonder that he made several appearances during the show’s run, becoming more successful as a comic, but never getting any better or any wiser. Bania was given the ultimate compliment long after Seinfeld ended, by being one of very few recurring characters resurrected for that show’s “reunion” episode of Curb Your Enthusiasm. Unlike the profoundly irritating Randy, whose success seems to grow as your faith in humanity diminishes, Bania is more of an infectiously adorable nuisance, and it’s nice to know that he’s still out there somewhere, as ecstatic as ever over jokes that aren’t as clever as he thinks they are.

5) Krusty the Clown (The Simpsons)

Krusty the Clown has provided us with much cause for laughter over the years…just not where he wanted us to find it. His Krusty the Clown Show sketches are the stuff of huge mustaches and pie fights, something that might be written by somebody who grew up watching classic comedians, but could never figure out why they were supposed to be funny. In fact, his comedy routines are so poor that they drove at least one of his previous sidekicks to criminal insanity. The humor behind Krusty comes from the incongruity of his situation: he’s a children’s entertainer who openly dislikes children, even when the cameras are rolling. His drug and booze fueled lifestyle allow him to coast lazily through whatever appearances he’s contractually obligated to make, but beyond that he’s a comedian who doesn’t particularly care whether or not you find him funny…he gets paid either way. In fact, in one episode (“The Last Temptation of Krust”) Krusty does become inspired to develop as a stand-up comedian, and achieves a new peak of notability with his more mature, insightful material. And then, of course, somebody offers him money, and he realizes that that’s his real passion. Krusty isn’t a hack because he doesn’t have the talent; he’s a hack because he’d rather make easy money than work hard. It’s an ethos so powerful and seductive that it eventually infected the writing of The Simpsons itself.

6) Dee Reynolds (It’s Always Sunny in Philadelphia)

You’d be hard pressed to describe any of the main characters in It’s Always Sunny in Philadelphia as sympathetic, but you’d probably have the easiest time with Dee, if only because she seems to be aware that she’s missing out on something greater in the world. For all their grumbling and groaning, Mac, Dennis, Charlie and Frank are all actually pretty content where they are, and with who they are. They don’t have much of a desire to achieve even a measure of self-awareness, let alone anything bigger for themselves. Dee, on the other hand, does have aspirations: she wants to be an actress. With so little experience and talent behind her, though, she isn’t even sure where to begin, which is why she regularly subjects herself to delivering dire stand-up comedy at The Laff House. She explains this to Charlie — the only one in whom she’s confided about her performances — by saying she’s paying her dues. After all, if she wants to be an actress, she has to learn how to hold an audience. Fair enough, but when her set degenerates immediately into a series of painful and repulsive dry heaves, it’s clear that this is a gesture of self-mutilation, rather than any experience she’s likely to benefit from. Charlie, meanwhile, eats cat food. He’s the happier one.

7) Geoff Tipps (The League of Gentlemen)

The brilliant third series of The League of Gentlemen found many of its characters being thrust well outside of their comfort zones, an evolutionary direction for the show that resulted in much of its best — if not necessarily funniest — material. For Geoff Tips, this meant leaving the small town of Royston Vasey to pursue a stand-up comedy career in London. This is not a career change that’s destined to go well, particularly as we’ve already seen him botch jokes so badly that he’s threatened to shoot people for not laughing, and play practical jokes on his friends that involve him staging a gory suicide in a restaurant bathroom. Comedy is not Geoff’s forte, but it is his passion, and so, when he loses his job in “Turn Again, Geoff Tipps”, the comedy club is the first place he turns. Of course he bombs in more ways than one, not only allowing his act to dissolve into a shouting match with dissatisfied audience members, but also by serving as the unwitting chauffeur for a terrorist car bomb on behalf of the IRA. Still, you’ve got to laugh, haven’t you?

8) GOB and Franklin Bluth (Arrested Development)

Comedy is not GOB Bluth’s strong point. Nor is puppeteering. Nor music. Nor ventriloquism nor respecting the delicacy of race relations. It’s pretty clear then that his act with Franklin is going to go about as well as anything else he’s done. That won’t stop GOB, however, because GOB is one of those people who believes that everything he does is being done well, simply by virtue of the fact that it’s he who is doing it. He sees himself as preternaturally gifted in all areas he attempts to explore, and often this premature self-satisfaction is so seductive that others get sucked in as well. In the case of Franklin Delano Bluth — the puppet who reminds us that it’s not easy being brown — however there’s not much to get on board with. His racially-charged banter with the dead-eyed Franklin is stymied by the fact GOB can’t keep his lips from moving, ultimately resulting in his desperately hiding a tape recorder inside the puppet as a substitute for using his own voice. Unfortunately, GOB’s lips still move, even though he’s not saying anything, and the act is just as doomed as it ever was. As a character, GOB rarely says or does anything genuinely clever; rather, he works so well as a comic figure because of just how artfully he gets everything wrong. And speaking of puppets…

9) Joe Beazley and Cheeky Monkey (Knowing Me, Knowing You… With Alan Partridge)

Of all the characters on this list, Joe Beazley and Cheeky Monkey are the only ones who have just a single appearance to their credit. Even Randy continued to exist outside of the film that gave him life. Joe Beazley and Cheeky Monkey, however, so thoroughly squandered their chance at fame that they were never heard from again, in any form, ever. Just one of many, many, many things to go wrong for Alan Partridge on his ABBA-inspired chat show, Joe Beazley — suffering obvious and debilitating stage fright — bungles his performance so badly than Alan is forced to shut it down almost immediately…much to Joe’s chagrin. Joe starts out by bungling a joke that he improvised just minutes before in the green room, and it only gets worse from there. This comedy misfire wasn’t quite as damaging to Alan’s television career as the fact that he later shot another guest through the heart with a dueling pistol on live television, but the bitter taste of Joe Beazley’s routine with Cheeky Monkey lingers on to this day; he was one of the performers Alan saw fit to call out and specifically berate in his recent memoir, I, Partridge. Alan’s not one to let go of disappointment easily, and this laugh-free puppet fiasco affected him so profoundly that he used it as justification for never again giving up-and-coming performers a break. Ooh, you cheeky monkey.

10) Steve Martin

Why are we ending on an actual comedian? Well, because Steve Martin, in terms of his stand-up anyway, was always a very deliberate creation. What you saw on stage wasn’t Steve Martin the man, but Steve Martin the character. His arrow through the head, his balloon animals, his belabored “Well ex-cuu-uu-uuse me!” were all meant as clever pieces of anti-comedy. When he took to the stage, he did so as a walking caricature of the worst that stand-up comedy had to offer. Needless to say, audiences loved it, and Martin was given higher profile gigs, such as a record-breaking number of appearances on Saturday Night Live, and also more classic films than we can remember. The public initially decided they loved Steve Martin because he shined a spotlight on things that weren’t funny, but he did so in such an endearingly committed way that they just had to laugh. And then, once he had everybody’s attention, he showed the world that he knew comedy so well that he’s since stood as an important cultural fixture, spanning decades while lesser comedians — including many who unintentionally resembled the act that made him famous — came and went. And the moral of Steve Martin’s story is the most important lesson to keep in mind here: anyone can write a bad joke, but it takes a sincerely gifted people to craft these characters that are so perfectly bad in all the best ways.

How I Would Honor The Three Stooges

The Farrelly Brothers have been promoting their movie The Three Stooges by saying that first and foremost they wanted to pay tribute to the originals. Well, their movie is out this weekend, and from all accounts it doesn’t sound like all that flattering a tribute.

Personally, here’s how I’d pay proper tribute. I know it’s complicated, so I’ve tried to break it down into simple steps.

1) Take some time and go through all the surviving Stooge shorts. From these, take about 80 minutes’ worth of the best and most memorable material. You can narrow it down to a few complete shorts, or mix and match sequences from however many you like. I can see pros or cons either way. The important thing is, you’re using the originals, and not some lesser, artless stab at joyless re-creation.

2) Get someone knowledgeable and well-respected in the film industry to record an introduction for you. Roger Ebert won’t do for obvious reasons, but I’m sure you can find somebody important to speak for a minute or two about what the Stooges did for comedy, and how they influenced just about every physical comedian to come. This will be the first thing audiences see, because it’ll be comparatively boring and we want it out of the way early. Allot time for a pie in the face.

3) Draft a bunch of your Hollywood friends and colleagues to record new and interesting linking material. If they were willing to commit to humiliating cameos in the backyard horseplay you call a tribute film, I’m sure they’d be at least as willing to do this instead. Some of them might even come away from the project with some measure of self-respect, which would make for a nice selling point by comparison.

4) Edit it all together into A Celebration of The Three Stooges, or something. I don’t care. Call it a Tribstooge if you want. It doesn’t matter. Just as long as your centerpiece is original material, lovingly restored and considerately presented, featuring sincere reminiscences and discussions by contemporary stars and artists who appreciated them. Release it for one night only, or maybe schedule several showings over one weekend, to spur ticket sales and contribute to an overall sense of being part of an appreciative community.

5) There is no five. There are only four steps. This is fucking easy.

Of course, such a gambit might not make as much money as a major Hollywood film, but it would certainly cost a hell of a lot less than the monstrosity we have instead…and the profits on that one are yet to be determined anyway.

Then again, what do I know? We’re obviously in the hands of capable professionals.

Billy’s Gourmet Hot Dogs

Just a quick post to give a lot of love to Billy’s Gourmet Hot Dogs, for basically just being awesome. Oh, and for opening another restaurant closer to where we live now, even if they had the audacity not to tell us.

I’m not exaggerating when I say that Billy’s is the only thing I miss about our old apartment. In fact, between the defecating hobos and gang wars Billy’s was about the only thing I felt comfortable looking at directly. And it was delicious.

My girlfriend and I fell in love with that place soon after I moved in. She’d never been there, despite living right next door, but I changed that. She started making me eat salad, so in an act of supreme revenge I forced her to eat hot dogs. Personally, I think she got the better end of the deal.

Before we moved we bought mugs with the Billy’s logo on them, so we wouldn’t forget their almost criminally perfect hot dogs. (White Hot, I’m looking at you.) But we didn’t need them, because we still go back pretty regularly. It’s worth driving that far. Order the garlic pesto blue cheese fries just once and see if I’m lying.

The service is also fantastic, with Billy himself and Billy Jr. on hand to give out samples, suggest concoctions not on the menu (HELLO, MAC DADDY!!) and just generally be excellent human beings.

We haven’t been to the new location yet, but my girlfriend and I were glad to see that Billy was doing well enough to expand. It couldn’t have happened to a nicer guy.

Also, according to their website they cater. So if you’re getting married, let them make you a shitload of hotdogs. And also invite me.

Because I fucking love these hot dogs.

Noiseless Chatter Spotlight: The Long Goodbye (1953)


The law isn’t justice. It’s a very imperfect mechanism. If you press exactly the right buttons and are also lucky, justice may show up in the answer. A mechanism was all the law was ever intended to be.

NOTE: This article is spoiler-free, for those who care about that. How I managed to write over three thousand words about a mystery without spoiling anything is a case I’ll never be able to solve.

There’s something sad about a man losing everything. There’s something even sadder about a man who has nothing finally finding himself with something to lose. It won’t stick around…it can’t stay. The universe can’t let you get away with happiness for too long. At least, that’s the kind of thing Philip Marlowe might think. And by the time we join up with him — toward the very end of a long, cruel and dangerous career — we really can’t blame him.

After a few false starts with interchangeable detective figures known as Dalmas and Mallory and Carmady, Raymond Chandler stumbled upon the name Philip Marlowe, and from then forward that was the only name he used. And with a steady name came the benefit of cumulative characterization. World building was not only made easier, it became a sort of passive necessity. And as Chandler plumbed the depths of this character who originated as nothing more than a pawn to be manipulated by the conventions of the genre, he graduated from fictionist to author. Marlowe did that for him. And in return, Chandler allowed his creation to star in some of the most effectively literary experiments detective fiction is ever likely to have.

But while Chandler’s star was on the rise, Marlowe’s was on an eternal decline. The long-suffering private detective was regularly insulted, beaten, stabbed, shot, brained, double crossed, left for dead and rejected by the world around him. And yet, like Charlie Brown and the football, he never gave up. Something kept Marlowe moving forward. Something stopped him from turning in his license and going to work in a hardware store — an alternate existence he ponders here in The Long Goodbye. Something compelled him to press on with his thankless job that would no doubt, in time, get him killed. And that something was an unflagging sense of justice.

For Marlowe, justice and the law are two separate entities that occasionally overlap, but are no substitutes for one another. The quote that opens this article comes from Sewell Endicott, a well-meaning but easily manipulated lawyer, but his observation echoes Marlowe’s own philosophy. The laws are rules that only really work to keep people in line who don’t press against them — in other words, they are only really of use to those who wouldn’t break them. For everybody else, there needs to be a different kind of justice. There needs to be a super-legal vigilance that punishes and redresses “wrong,” as opposed to “illegality.” That vigilance is missing from this world. Marlowe figures — more or less correctly — that it will either come from himself, or from nowhere. And so he slips a gun into his pocket, dons a fedora, and hopes nobody will notice last night’s black eye. It will kill him, but justice is larger than he is. The world can live without Philip Marlowe, but it can’t — or shouldn’t — continue on without somebody keeping the cosmic moral compass in check.

The police, interestingly, are often portrayed as Marlow’s biggest adversary. While he goes up against gangsters and thieves and thugs and murderers nightly, he knows what to expect from them. They make no convincing overtures that they are anything but villains, and Marlowe simply has to keep himself from getting killed until he finds an opening to bring them down. The police, on the other hand, claim to want the same thing he wants; they just have a different method for achieving it. Their method has the force, their method has the reach, and their method has the power. They are a national, well-organized and infinitely funded resource. Marlowe is a quiet man standing sour-faced in the rain. The former sees success when they close out a case…regardless of the accuracy of its outcome. Marlowe’s success is a more difficult, less quantifiable result: justice. He doesn’t always know how he’ll get there, or what it means, but he knows he’ll recognize it when he finds it.

Sewell Endicott is a prime example of what frustrates Marlowe about the legal process. He’s a good person who genuinely wants to see a case closed correctly. He follows proper procedure and asks all of the questions he is supposed to ask. However when placed up against those who know how to respond to those questions in such a way that satisfies Endicott but leaves the truth buried, he’s helpless. Marlowe sees this. The case is closed. The murder is solved and the murderer has been brought to some kind of justice. Only Marlowe doesn’t buy it. Something doesn’t fit. Endicott asks all of the questions he is supposed to ask. Marlowe endangers his own life by asking everything else. That’s the difference.

Or, rather, a difference. Marlowe’s sense of right and wrong is his own…a hyper-personal arbitration by which we are all judged, separate from and alternately looser and stricter than the more tangible “law.” Philip Marlowe is Chandler’s Ozymandias. The ends for him always justify the means, as he withholds evidence, obstructs and often derails the judicial process in aid of some grander, more solvent statement that will have a wider-reaching and fairer outcome than a standard criminal investigation ever could. And as with Ozymandias, a lot of innocent people get hurt along the way.

When I started reading Chandler a few years back, I thought I knew what to expect. And, in a way, I did. Detective fiction is a comparatively rigid genre. It has its rules and it wears them on its sleeve. Very rarely does detective fiction aim to achieve anything beyond a satisfying mystery cleverly resolved. And, in fact, that’s what Chandler was providing throughout an enormous portion of his career. Writing stories of about fifty pages each gave him just about enough room for a setup, a twist, a gunfight and a resolution. Along the way he might have stumbled over interesting characters or dynamics, but there wasn’t any time to explore them. That’s part of why, beginning with The Big Sleep, his first novel, Chandler turned back to his old stories…combining and manipulating and deepening them. It’s not that he didn’t know how to flesh out a novel, it’s that he had already written novels that were confined to 50 pages each, and wanted now to give them some breathing space. Going from 50 pages to 300 gave him a lot more room to explore these situations and these characters and their motivations. And going from one novel to an entire series gave him exponentially more room to explore Marlowe, and to test his unwavering morality against temptations of all kinds: personal, financial, carnal…and, in The Long Goodbye, devotional.

The Long Goodbye is Chandler’s final major work starring Philip Marlowe. It’s also, without question, my favorite of Chandler’s writings. Coming as it does toward the end of Marlowe’s career, the accumulated impact of tragedies lends this book an intriguing sense of weariness. Marlowe’s compass is as accurate as ever, but his body is broken. His drive is slowing down. His world view is stained permanently by the blood of the past. All of this is to say that Marlowe, here, is weaker than he’s ever been. Which allows him to make his ultimate mistake: befriending another human being.

Yes, The Long Goodbye is a story of friendship, much like previous spotlights Double Indemnity and “AWESOM-O.” But in this case the friendship is much more to the forefront, and is, in fact, the driving force behind the entire novel. In fact, it may even be the driving force behind everything Marlowe says and does this time around. His characteristic — and highly personal — morality is still on display, but it sometimes takes a back seat to the devotion and loyalty he has for his friend, Terry Lennox.

It’s easy to see why Marlowe feels so drawn toward Terry Lennox. He first meets him outside of an expensive club, where Lennox is first rejected and then physically removed from his own vehicle by the woman he’s with. He’s drunk, he’s broke, and he’s abandoned. The woman, his ex-wife Sylvia, drives off without him, and the doorman leaves him to lie embarrassingly on the pavement. Marlowe sees him there, scarred up from an old war injury and left to rot on streets that will never care whether he lives or dies, and he lifts him up. He takes him home. He sees himself in Lennox…a hopeless case that will never learn, but one with a good heart. As the novel unfolds, we learn that the disfiguring injury was actually the result of a wartime sacrifice, as he allowed himself to be nearly killed by a detonating shell so that his squadron might live. Marlowe slowly begins to feel accountable for Lennox. Nobody else will so much as speak to him, but Marlowe takes him home, joins him regularly for drinks, and eventually even allows the man to take him into his confidence about his history…something Marlowe typically avoids specifically so that he won’t develop a human connection.

Friendship is new to Marlowe. In several novels, including this one, he has a mutually antagonistic relationship with Bernie Ohls, the only cop Marlowe consistently respects, but they clash over their methods and can’t entirely allow the other to be too satisfied with what they’re doing. This, one begins to feel, must be the only friendship Marlowe is comfortable with: one that simply will not come too close. Marlowe and Ohls are chained to separate posts. They might be able to pull themselves near enough to interact, but never will they share the same world. And that’s how Marlowe likes it, preferring to spend his nights alone in a rented room solving a book of chess problems than out with anybody who may eventually double cross him. As Bob Dylan would later observe, “When you ain’t got nothing, you’ve got nothing to lose.”

And Marlowe’s right to be so reticent, because everybody will double cross him. It’s what he’s learned…or, rather, it’s what the world has taught him. Nobody gets away with being happy for too long, and Marlowe, who has never allowed himself to be happy, seems to have skirted that tragedy with a loophole. By living in rented rooms and never allowing himself to indulge in human relationships, there is nothing for anybody — or anything — to take away from him. When he lets Terry Lennox in, he is opening the door to his own tragedy.

And sure enough, tragedy does strike. Lennox shows up at Marlowe’s home early one morning, and demands that he gets driven to Mexico. Marlowe takes him on the condition that Lennox doesn’t tell him why; if he knows a crime has been committed, he won’t morally be able to help him escape. While this is true to the technicality of Marlowe’s ethical bent, it’s a completely deliberate fudge; an intentional exploitation of a logistical blindspot. In short, it’s exactly what Marlowe dislikes about standard policework, and it’s our first clear indication that his devotion to Lennox has managed to supplant — or at least uproot — Marlowe’s guiding morality. We let it happen here in the real world, too…any time we allow our feelings toward our friends, or relatives, or spouses or children to take precedence over how we might otherwise behave without them. It’s what happens when we start to make decisions based on how other people might feel. For us, it’s a necessary and often rewarding part of adulthood. For Marlowe it’s a liability, and a failure on his part to sustain his integrity in a crime-laden universe.

Marlowe later learns that Sylvia is dead, bludgeoned horribly by a small bronze statuette, and almost completely unidentifiable. He goes to jail for several days where he is beaten and abused by his fellow agents of the law, but refuses to tell them anything about Lennox, or where he’s gone, or whether or not he might have been involved. He is released only when it is learned that Lennox has committed suicide in a hotel room in a small Mexican town. Case closed.

But for Marlowe, it isn’t over. The Long Goodbye uses the Lennox material as bookends. He may be dead, but the novel still has several hundred pages left to go, and as the title suggests, letting go of his old friend won’t be easy.

The first Philip Marlowe novel was The Big Sleep, whose title was a euphemism for death. It’s fitting then that the title of the final major work featuring Marlowe refers to the process of mourning. It also, though not by design, reflects the long goodbye we as readers are saying to Marlowe. The slight Playback is the only complete story he will feature in after this one, and that’s a much shorter goodbye, a brief and airy swansong that leaves little impact in the wake of the sprawling Long Goodbye that preceded it. Poodle Springs, the novel meant to follow that up, was never completed.

Letting go of his dead friend is further complicated by the letter Marlowe receives, which was mailed before the suicide and contains a note of appreciation and a $5,000 bill. Marlowe doesn’t spend it. He’s back to his old self, eschewing personal gain because he knows it will eventually lead to personal loss. He downplays the value of the bill by referring to it as a portrait of Madison.

But he’s a changed man. The impact of having had a friend — or, perhaps, the impact of having lost one — has left a different, more sentimental Marlowe in his place. In Lennox’s letter he asks Marlowe to remember him by preparing a cup of coffee and a cigarette…which is what they last shared before Marlowe brought him to Mexico. He also asks that Marlowe return to their favorite tavern and drink a gimlet on his behalf. Marlowe does the former almost immediately, but turns down many opportunities for the latter. He knows, after all, that once he does so, he will have finished his goodbye. He will have to come to grips with the fact that Terry Lennox is no more. He will have to come to grips, that is to say, with the fact that the one friendship we’ve ever known him to have no longer exists.

There’s a lot more in The Long Goodbye than what I’ve mentioned so far. There’s the long and difficult case of the Wades, of course, and there’s the gorgeous central chapter in which Marlowe, for once, narrates a simple day at the office. But it’s all a symptom of his fatigue. He refuses to become embroiled in the evolving tragedy of Roger and Eileen Wade, and his dour recitation of a dull workday’s worth of meaningless encounters just serves to underscore the hollowness he feels.

The Wade interlude — like the titular goodbye, it’s a long interlude — occurs between the two halves of the Lennox case. In fact, the structure of the novel is artfully chiasmatic: the Lennox setup, the Wade setup, the glorious middle section that features Marlowe being reflective (in more ways than one, natch), the Wade conclusion, and finally the Lennox conclusion. Such deliberate craftsmanship in a genre not famed for complex artistic flourishes comes, probably not coincidentally, in a novel that features an author character who questions his value to the literary world, when all he writes is easily-digestible pulp. Wade cannot escape the sense that he’s capable of more. Chandler reaches just a little further, and achieves it.

It’s also no coincidence that the woman Marlowe will eventually marry makes her first appearance in this book. This is the right time for him; he is at the crux of a major change, as Terry Lennox — the only and last pillar of humanity he believed in — is torn bloodily from his life. It’s not so much that Linda Loring comes along and Marlowe recognized his future in her, it’s that Marlowe needed direction and Linda Loring came along.

It is, however, a coincidence that Chandler died during the composition of Poodle Springs, the novel which would feature Marlowe as a married man, secure in a different kind of existence with a companionship and stability he never knew…and, indeed, as the novel was unfinished, would never get to know. Just another cosmic insult to the private eye, one last kick in the pants and assurance that, yes, it is your destiny to be abused and, yes, we will see to it that you never escape.

Knives and bullets and bats and fists never managed to break Philip Marlowe, but the friendship of another man did. And Marlowe, without having anything else in his past worth comparing it to, does not know how to cope. He keeps digging up dirt and second guessing details. The case is closed, Marlowe. Everything is over and people are happy. Please leave it alone.

But he doesn’t. Because something is missing. He may have had and lost an important friendship, but he wasn’t double crossed. He wasn’t used or abused or manipulated by the person that he foolishly let into his life. And for that reason, he knows it can’t be over. And he digs, and he fights, and he argues, all in the service of uncovering the truth of the betrayal of which he knows he must have been the victim.

It’s a bizarre and unsettling psychological subversion of the genre Marlowe once represented so cleanly. He is driven by the unscripted forces of right and wrong, compelled onward by a sense of justice nobody else on the planet seems to share or even understand. Typically this means he seeks to bring the bad guys down. In The Long Goodbye, however, he is fighting to become the victim himself. Everything is quiet, and everything worked out…and that’s impossible, because Philip Marlowe hasn’t been obviously betrayed. He hasn’t paid the price for violating his rule of human contact. And he won’t rest until he finds his wounds and rubs them raw. He will not stop until he’s forced himself to feel the pain he knows he must have earned. His compulsion toward justice has morphed gradually into a kind of self-abuse, a cycle of internal torment that Marlowe — in just about every way apart from the literal — won’t survive.

He suffers for justice, justice of any kind, any where, for any one, please, just somewhere let justice shine, let the wrong be punished and let the right be relieved, just once, please, before I die…and yet, when he finds it, he must simply begin again, with a new case, resetting the counter, as though the previous events never happened…yet retaining the scars it took him to get there. Once that sense of justice is turned inward, there is nothing he can do but self-destruct.

It’s a lot darker and more emotionally complex than I ever expected detective fiction to be, and it comes at — more or less — the very end of Marlowe’s career both as a private detective and as a character. I thought I knew what to expect. I thought Chandler was just going to give me another volume of entertaining and distant tragedy, trimmed and packaged for my approval.

I wouldn’t say it’s one of my favorite books, but I will say it was one of my favorite experiences as a reader, and I’m still not sure I know what to do with it. To paraphrase one of Marlowe’s observations about cops, just when I thought I knew what to expect, one of them had to go and get human on me.