The Ultimate Story Checklist: Sideways

Updated to the sixth and final checklist!

Miles, a miserable would-be novelist, takes his sex-addict best friend Jack for a weeklong trip in California wine country to celebrate Jack’s impending marriage. Jack announces that he intends to get them both laid, and he quickly hits it off with a wine clerk, Steph, then sets up Miles up with her friend Maya. Soon, Miles is in love, but he loses Maya when she finds that Jack has hidden his engagement from Steph. Miles finally accepts his miserable lot in life...just in time to get a hopeful call from Maya.

PART #1: CONCEPT 15/19
The Pitch: Does this concept excite everyone who hears about it?
Is the one sentence description uniquely appealing?	No. The logline sounds very unappealing. (Two miserable middle-aged men romantically pursue two divorcees during a week-long trip to wine country.)  This was sold largely on the writer-director’s reputation. We knew we could trust Payne, and he knew we trusted him and would let him make a low-concept movie.
Does the concept contain an intriguing ironic contradiction?	Not really for Miles, but yes for Jack, a man looking for love on the eve of his wedding.
Is this a story anyone can identify with, projected onto a bigger canvas, with higher stakes?	Very identifiable, but not really bigger, except for the two “Holy Crap” moments.
Story Fundamentals: Will this concept generate a strong story?
Is the concept simple enough to spend more time on character than plot?	Very much so.
Is there one character that the audience will choose to be their “hero”?	Miles.
Does the story follow the progress of the hero’s problem, not the hero’s daily life?	It breezes through seven days of story, which is more than most movies
Does the story present a unique relationship?	A divorced middle-age man and his middle-aged best friend who is getting married for the first time.
Is at least one actual human being opposed to what the hero is doing?	Jack is opposed to Miles’ idea of not meeting someone, then opposed to Miles’ need to confess, Maya and Steph are opposed to his lying.
Does this challenge represent the hero’s greatest hope and/or greatest fear and/or an ironic answer to the hero’s question?	It’s his greatest fear (losing his ex and his hopes of publication)
Does something inside the hero have a particularly volatile reaction to the challenge?	Yes.
Does this challenge become something that is the not just hard for the hero to do (an obstacle) but hard for the hero to want to do (a conflict)?	He’s still in love with his ex-wife and the idea of himself as a novelist.
In the end, is the hero the only one who can solve the problem?	No. He chooses to wait for Maya to reach out to him, but it’s clear that she does so because of his efforts: his call confessing all, and the quality of his novel.
Does the hero permanently transform the situation and vice versa?	Transform situation: He doesn’t really change Jack, but he changes Maya. Transform self: Yes, he has huge breakthroughs
The Hook: Will this be marketable and generate word of mouth?
Does the story satisfy the basic human urges that get people to buy and recommend this genre?	Not really. It has little of the usual joys of the manchild-driven comedy (T&A, turning tables on snobs, etc.).
Does this story show us at least one image we haven’t seen before (that can be used to promote the final product)?	Vineyards, noses in wine glasses.
Is there at least one “Holy Crap!” scene (to create word of mouth)?	Drinking the spit bucket, interrupting the post-cuckold sex
Does the story contain a surprise that is not obvious from the beginning?	Not really. It’s pretty obvious that the truth is going to come out.
Is the story marketable without revealing the surprise?	NA
Is the conflict compelling and ironic both before and after the surprise?	NA
PART #2: CHARACTER 21/22
Believe: Do we recognize the hero as a human being?
Does the hero have a moment of humanity early on? (A funny, or kind, or oddball, or out-of-character, or comically vain, or unique-but-universal “I thought I was the only one who did that!” moment?)	Hmm…I think we need a new category: the moment of chutzpah. We admire his careless contempt for the people calling him to show up the party.
Is the hero defined by ongoing actions and attitudes, not by backstory?	He’s focused on his past, but we’re not. We see that it’s his action and attitudes that are the problem, not the past.
Does the hero have a well-defined public identity?	The lovable sad-sack novelist
Does the surface characterization ironically contrast with a hidden interior self?	He actually knows that he’s not good enough to be a writer, and he’s hiding a lot of darkness and bitterness.
Does the hero have a consistent metaphor family (drawn from his or her job, background, or developmental state)?	Metaphors themselves: “At my age, if you don’t have any money, you’re just a pasture animal waiting for the abbatoir” “I’m a thumbprint on a skyscraper.” Also wine: “This whole week has gone sour.”
Does the hero have a default personality trait?	Negativity.
Does the hero have a default argument tactic?	Traps people. / emotional blackmail “Did you like the new ending?” “Yes.” “Everything after page 750 is exactly the same.” / “Just wanted to let you know I’m not coming to the wedding.”
Is the hero’s primary motivation for tackling this challenge strong, simple, and revealed early on?	Have a fun drunken week.
Care: Do we feel for the hero?
Does the hero start out with a shortsighted or wrongheaded philosophy (or accept a false piece of advice early on)?	“[Dating is] not worth it, you pay too high a price.”
Does the hero have a false or shortsighted goal in the first half?	Give his friend a great last week of freedom.
Does the hero have an open fear or anxiety about his or her future, as well as a hidden, private fear?	Open: His novel won’t get published.  Hidden: His novel isn’t any good.
Is the hero physically and emotionally vulnerable?	Moreso emotionally, but both.
Does the hero have at least one untenable great flaw we empathize with? (but…)	Many: he’s a morose, duplicitous, unfaithful, hostile, and an alcoholic who steals from his mom.
Invest: Can we trust the hero to tackle this challenge?
…Is that great flaw (ironically) the natural flip-side of a great strength we admire?	Yes, though it’s not immediately obvious. He’s a great conversationalist, when he puts his mind to it (even when he’s forced to spend the evening with his friend’s girlfriend’s mother, she says “It was really great talking with you!”)  He’s also a good writer, and therefore a good observer of people.
Is the hero curious?	He figures a lot of stuff out.
Is the hero generally resourceful?	He steals money, manipulates people, steals extra wine, etc.
Does the hero have rules he or she lives by (either stated or implied)?	“I AM NOT DRINKING MERLOT!” I’m too good for this (job/girl/situation), etc.
Is the hero surrounded by people who sorely lack his or her most valuable quality?	They all seem dopey in contrast to his cynicism.
…And is the hero willing to let them know that, subtly or directly?	He has a withering, sharp wit.
Is the hero already doing something active when we first meet him or her?	No. He shows up late. He’s a lazy guy.
Does the hero have (or claim) decision-making authority?	Although he’s powerless to stop Jack from getting anything he wants.
Does the hero use pre-established special skills from his or her past to solve problems (rather than doing what anybody would do)?	He wins Maya over with his wine knowledge and his novel.
PART #3: STRUCTURE (If the story is about the solving of a large problem) 17/21
1st Quarter: Is the challenge laid out in the first quarter?
When the story begins, is the hero becoming increasingly irritated about his or her longstanding social problem (while still in denial about an internal flaw)?	He’s tired of being a depressed drunk.
Does this problem become undeniable due to a social humiliation at the beginning of the story?	He has to move his sloppily parked car, oversleeps for friend’s party.
Does the hero discover an intimidating opportunity to fix the problem?	His friend promises to get him laid.
Does the hero hesitate until the stakes are raised?	He refuses, insists that Maya is married.
Does the hero commit to pursuing the opportunity by the end of the first quarter?	…but just barely. At minutes 32 of a 127 minute movie, he reluctantly accepts an arranged date with Maya.
2nd Quarter: Does the hero try the easy way in the second quarter?
Does the hero’s pursuit of the opportunity quickly lead to an unforeseen conflict with another person?	Jack, who wants him to drink Merlot, and insists he be fun, but tells him right beforehand that his ex got remarried
Does the hero try the easy way throughout the second quarter?	He gets blind-drunk for most of the date.
Does the hero have a little fun and get excited about the possibility of success?	Not at this point, but it happens in the first and third quarter, with lots of beautiful driving and drinking montages.
Does the easy way lead to a big crash around the midpoint, resulting in the loss of a safe space and/or sheltering relationship?	A mild one: He responds too late when she makes a pass, and convinces himself that he’s blown it. Worse, Jack and Steph hit it off, seeming to ruin the rest of the trip. Jack disappears, the motel room and restaurant are miserable alone.
3rd Quarter: Does the hero try the hard way in the third quarter?
Does the hero try the hard way from this point on?	Eventually. He finally goes to the restaurant to ask about her, but misses her, but she reaches out to him the next day.
Does the hero find out who his or her real friends and real enemies are?	Realizes he should have been loyal to Maya, not Jack.
Do the stakes, pace, and motivation all escalate at this point?	He and Maya have sex, possibly fall in love…
Does the hero learn from mistakes in a painful way?	Maya realizes that Jack is getting married, and dumps Miles.
Does a further setback lead to a spiritual crisis?	He finds out his novel isn’t getting published, and he admits that he’s not going to make it as a novelist, isn’t a good person.
4th Quarter: Does the challenge climax in the fourth quarter?
Does the hero adopt a corrected philosophy after the spiritual crisis?	Before, actually: “This has been a big deal for me.” In this case, the further hardships cause him to regress, not progress, but the progress he’s already made finally pays off much later.
After that crisis, does the hero finally commit to pursuing a corrected goal, which still seems far away?	No. He recommits to the false goal of making Jack happy, even retrieving his wedding rings after his adultery.
Before the final quarter of the story begins, (if not long before) has your hero switched to being proactive, instead of reactive?	Sort of. He never becomes proactive. Maya has to finally reach out to him, and it takes a huge effort just to be reactive, and drive to see her. BUT, they’ve set up a situation in which one of his big problems is drunk-dialing, so, ironically, it seems somewhat heroic that he doesn’t reach out to her, and waits for her to call.
Despite these proactive steps, is the timeline unexpectedly moved up, forcing the hero to improvise for the finale?	No, even when she calls, she leaves a message telling him to call back anytime.
Do all strands of the story and most of the characters come together for the climactic confrontation?	No. Miles and his ex run into each other at Jack’s wedding, but Maya and Steph aren’t there.
Does the hero’s inner struggle climax shortly after (or possible at the same time as) his or her outer struggle?	After.
Is there an epilogue/ aftermath/ denouement in which the challenge is finally resolved (or succumbed to), and we see how much the hero has changed (possibly through reversible behavior)	He drives north and knocks on her door. There’s no reversible behavior…they could have ended with him drinking merlot to show he’s changed, but that would have been too on the nose (no pun intended.)
PART #4: SCENEWORK (Selected Scene: Miles has struck out with Maya, but Jack comes back to the motel after a wild night with Steph, intending to go back out. Miles tries to get Jack to stay by forcing him to call his fiancé, but she doesn’t answer and Jack takes off with Steph after getting Miles to return his unused condom from the night before.) 16/20
The Set-Up: Does this scene begin with the essential elements it needs?
Were tense and/or hopeful (and usually false) expectations for this interaction established beforehand?	Miles has been stewing and watching messages piling up on the motel phone.
Does the scene eliminate small talk and repeated beats by cutting out the beginning (or possibly even the middle)?	Not the beginning but elides the middle when Miles steps outside while Jack lies, cutting out stuff we don’t need to hear.
Is this an intimidating setting that keeps characters active?	There are messages waiting and phones ringing, and Jack is literally running in and out.
Is one of the scene partners not planning to have this conversation (and quite possibly has something better to do)?	Jack had not planned on having a conversation.
Is there at least one non-plot element complicating the scene?	Not really. It’s a slim scene.
Does the scene establish its own mini-ticking-clock (if only through subconscious anticipation)?	Stephanie is outside and we hear her motorcycle running the whole time.
The Conflict: Do the conflicts play out in a lively manner?
Does this scene both advance the plot and reveal character through emotional reactions?	Yes, but it’s more plot than character. This is painful for Miles, but just an annoyance for Jack.
Does the audience have (or develop) a rooting interest in this scene (which may sometimes shift)?	We totally share Miles’s frustration
Are two agendas genuinely clashing (rather than merely two personalities)?	Miles wants to hang out, Jack wants to get laid again.
Does the scene have both a surface conflict and a suppressed conflict (one of which is the primary conflict in this scene)?	Surface: You need to call your fiancé, suppressed: you’re ruining our trip.
Is the suppressed conflict (which may or may not come to the surface) implied through subtext (and/or called out by the other character)?	Miles talks about Jack betraying his fiancé instead of betraying him.
Are the characters cagy (or in denial) about their own feelings?	Miles doesn’t say Jack shouldn’t cheat, he just says to check his messages.
Do characters use verbal tricks and traps to get what they want, not just direct confrontation?	Tells him to check his messages.
Is there re-blocking, including literal push and pull between the scene partners (often resulting in just one touch)?	Jack taps Miles on the chest, signaling that he’s about to lie, then taps him on the chest again later to confirm his mastery.
Are objects given or taken, representing larger values?	Jack gives Miles money to pay for golf as a way of paying him off abandoning him, then demands the condom back.
The Outcome: Does this scene change the story going forward?
As a result of this scene, does at least one of the scene partners end up doing something that he or she didn’t intend to do when the scene began?	Miles gives up his condom, Jack checks his messages.
Does the outcome of the scene ironically reverse (and/or ironically fulfill) the original intention?	Not really. Jack gets what he wanted unironically, Miles’s “check your messages” ploy fails, but it’s not ironic, it’s just bad luck.
Are previously-asked questions answered and new questions posed?	Previously asked: Yes, about Steph. New questions: Not really.
Does the scene cut out early, on a question (possibly to be answered instantly by the circumstances of the next scene)?	No, it goes to the end.
Is the audience left with a growing hope and/or fear for what might happen next? (Not just in the next scene, but generally)	Not really. Miles is stuck in a holding pattern and we don’t feel much hope for it getting better or fear of it getting worse.
PART #5: DIALOGUE 15/16
Empathetic: Is the dialogue true to human nature?
Does the writing demonstrate empathy for all of the characters?	Very much so.
Does each of the characters, including the hero, have a limited perspective?	Very much so. The audience understands everybody much better than they do themselves.
Do the characters consciously and unconsciously prioritize their own wants, rather than the wants of others?	Mostly. Maya is a little too dedicated to reaching out to this unattractive and unappealing guy, but at least she maintains her wariness and self-respect the whole time.
Are the characters resistant to openly admitting their feelings (to others and even to themselves)?	Very much so.
Do the characters avoid saying things they wouldn’t say and doing things they wouldn’t do?	Jack and Miles avoid confronting each other artfully.
Do the characters interrupt each other often?	Very much so.
Specific: Is the dialogue specific to this world and each personality?
Does the dialogue capture the jargon and tradecraft of the profession and/or setting?	Yes, of the vineyards.
Are there additional characters with distinct metaphor families, default personality traits, and default argument strategies from the hero’s?	Metaphor family: Jack: frat, Steph: sex, Default personality trait: Jack: optimism, sociopathy, Argument strategy: Jack: not listening to objections, hiding unpleasant info until the last second.
Heightened: Is the dialogue more pointed and dynamic than real talk?
Is the dialogue more concise than real talk?	Yes.
Does the dialogue have more personality than real talk?	“Never had the wallet for that” rather than money, for instance.
Are there minimal commas in the dialogue (the lines are not prefaced with Yes, No, Well, Look, or the other character’s name)?	Yes.
Do non-professor characters speak without dependent clauses, conditionals, or parallel construction?	Even the novelist / teacher avoids such language.
Are the non-3-dimensional characters impartially polarized into head, heart and gut?	Jack and Miles are 2-way polarized: careful pessimism vs. reckless optimism.
Strategic: Are certain dialogue scenes withheld until necessary?
Does the hero have at least one big “I understand you” moment with a love interest or primary emotional partner?	Yes, a few.
Is exposition withheld until the hero and the audience are both demanding to know it?	Info about the marriage and the women leaks out slowly.
Is there one gutpunch scene, where the subtext falls away and the characters really lay into each other?	Miles has one as Maya is dumping him, and Jack has one after the ostrich attack.
PART #6: TONE 10/10
Genre: Does the story tap into pre-established expectations?
Is the story limited to one genre (or multiple genres that are merged from the beginning?)	Combines male-bonding comedy / romantic drama, which is a somewhat awkward combination, but it’s maintained and it works.
Is the story limited to sub-genres that are compatible with each other, without mixing metaphors?	Also somewhat awkwardly: the bachelor party movie / the food-porn movie (wine-porn in this version)
Does the ending satisfy most of the expectations of the genre, and defy a few others?	He ends up with the girl, but he doesn’t have to change in order to do it.
Separate from the genre, is a consistent mood (goofy, grim, ‘fairy tale’, etc.) established early and maintained throughout?	When he apologizes for oversleeping and promises he’s out the door, then we cut to him reading on the toilet reading, which gets the first of many mordant chuckles from us, then we see him doing the crossword while driving! The audience freaks out, but the camera doesn’t.
Framing: Does the story set, reset, upset and ultimately exceed its own expectations?
Is there a dramatic question posed early on, which will establish in the audience’s mind which moment will mark the end of the story?	The wedding is coming up, they talk about when he’ll drink the 1961 wine, and Jack pledges to hook Miles up.
Does the story use framing devices to establish genre, mood and expectations?	Just slightly: We start with a title card saying “SUNDAY”, then they announce a weeklong trip and we get “MONDAY”, letting us know the shape of the movie.
Are there characters whose situations prefigure various fates that might await the hero?	He fears he can’t pursue love without becoming Jack.
Does foreshadowing create anticipation and suspense (and refocus the audience’s attention on what’s important)?	Lots of times the wedding almost comes up. Early shot of him doing crossword while driving establishes that he values doing the crossword over his own safety, so this sets up the fact that he accidentally confesses the wedding to her while doing the crossword. This would seem too careless if his carelessness had not bee well established.
Are reversible behaviors used to foreshadow and then confirm change?	He finally finds the courage to not call.
Is the dramatic question answered at the very end of the story?	We get the wedding, drinking the wine and hooking up one after another, the end.
PART 7: THEME 14/14
Difficult: Is the meaning of the story derived from a fundamental moral dilemma?
Can the overall theme be stated in the form of an irreconcilable good vs. good (or evil vs. evil) dilemma?	Blind optimism vs. clear-eyed cynicism, push for more out of life or accept less.
Is a thematic question asked out loud (or clearly implied) in the first half, and left open?	Jack’s future father in law says “I like non-fiction, there is so much to know about this world, I think you should read something if someone just invented it, waste of time.” Is it better to invent your own narrative of life or tell the truth?
Do the characters consistently have to choose between goods, or between evils, instead of choosing between good and evil?	Betray Jack or Maya? Lie to Jack about telling Maya to maintain friendship? Protect Jack from the consequences of actions or not?
Grounded: Do the stakes ring true to the world of the audience?
Does the story reflect the way the world works?	Very much so.
Does the story have something authentic to say about this type of setting (Is it based more on observations of this type of setting than ideas about it)?	Very much so. It feels like Payne must be a local, though he isn’t.
Does the story include twinges of real life national pain?	Bush and Rumsfeld on TV of screwed-up couple, collapse of publishing industry, death of the creative class.
Are these issues and the overall dilemma addressed in a way that avoids moral hypocrisy?	Yes.
Do all of the actions have real consequences?	…although Jack somehow manages to lie the consequences away after they hit.
Subtle: Is the theme interwoven throughout so that it need not be discussed often?
Do many small details throughout subtly and/or ironically tie into the thematic dilemma?	Facts about wines mirror Miles’ predicament (needing to be nurtured and protected, for instance), the quote from “A Separate Peace” at the end resonates, he prefers the dark wedding cake,  etc.
Are one or more objects representing larger ideas exchanged throughout the story, growing in meaning each time?	The bottle of wine, the condoms, etc. Yes, the manuscript, the wine bottle, etc.
Untidy: Is the dilemma ultimately irresolvable?
Does the ending tip towards one side of the thematic dilemma without resolving it entirely?	It looks askance at both of our heroes’ philosophies (Jack’s boundless optimism vs. Miles’s clear-eyed cynicism), but refuses to privilege either one over the other. Ironically, each man achieves his own goal by reverting to type at the end and fails to influence the other one: Jack’s outrageous positive-thinking lies pays off for him, and Miles’s cynical honesty pays off for him.
Does the story’s outcome ironically contrast with the initial goal?	Yes, Miles finds that the way to get the girl is the have the courage to do nothing, waiting for her to re-approach instead of drunk dialing her.
In the end, is the plot not entirely tidy (some small plot threads left unresolved, some answers left vague)?	It’s not clear what will happen when he shows up at her door.
Do the characters refuse (or fail) to synthesize the meaning of the story, forcing the audience to do that?	We never hear the final conversation. He doesn’t say what the kid’s essay means to him, etc.

Final Score: 108 out of 122