Hollywood Screenwriting Directory

Sideways (2004)

Screenplay Genre: Indie Comedy / Drama / Romance

Movie Time: 126 minutes

Synopsis: Depressed writer Miles (Paul Giamatti) and aging actor Jack (Thomas Haden Church) take a trip through the California Wine Country the week before Jack’s wedding with two very different agendas. Jack wants to have one last fling before marriage and Miles wants to have a fun week with his best friend. Along the way they are detoured by waitress Maya (Virginia Madsen) and winery employee Stephanie (Sandra Oh). Through a series of comic incidents the two ultimately learn a lot about the nature of human relationships and the faults of each other.


ACT I – On the Road to Wine Country

SEQUENCE ONE

World of the Story: Buddy Road Trip Indie comedy set to the backdrop of California Wine country: Dysfunction, depression, and budding mid-life crises.

Introduce Protagonist (Fool): Miles is a time wasting pathological liar.

Status Quo: Miles is a middle-aged, recently divorced, wine connoisseur, unsuccessful novelist/English teacher past his prime on the verge of publishing his first novel. He lives in a crappy apartment in California. He’s depressed, unrealistic, and stuck in the past.

Introduce Supporting Protagonist (Fool): Jack is a middle-aged, conceited, womanizing, liar still stuck in his glory days as a commercial actor.

Dramatic Premise: Miles and Jack both need to take the next step in life, and neither is ready.

Protagonist Objective: Miles wants to impress his best friend Jack and treat him to a bachelor party week in Wine Country before he marries into an upper middle-class family.

Act I Obstacle: Miles doesn’t have any money.

Status Quo Obstacle: Miles can’t move on with his life because he’s still not over his ex-wife.

Obstacle Solution: Miles takes a detour on the trip to visit his mom under the premise that they’re visiting her for her birthday. He steals some money from her underwear drawer cash stash.

Inciting Incident (Plot Point #1):Jack and Miles stop at a diner on their way up to wine country for Jack’s bachelor weekend. While Miles promises to show Jack a great week of golf and wine tasting, Jack promises to get the perennially depressed Miles laid.

(00: 17:24)


SEQUENCE TWO

Protagonist’s Objective (Miles): Teach Jack about wine, take him on a tour of Wine Country, tasting wines, golfing, and eating good food.

Protagonist Objective (Jack): Get Miles laid.

Introduce Antagonists: With all “Trip with Destination” scenarios, the situation itself is the primary external antagonist, but conflicts between characters act as internal antagonists.

Reveal: Jack reveals he may be making a mistake by marrying Christine (his fiancé) Miles gives him the advice that Jack’s “Waited a long time for some good reason” and he “Proposed to Christine for some good reason” But that he should “Keep his eyes open.”

Introduce Supporting Character (The Lover): Miles’s long-time crush Maya, recently divorced waitress in a restaurant Miles frequents in Wine Country.

The Lock In (Plot Point #2): Jack reveals that he also intends to get laid during the trip before he gets married, and he warns Miles not to get in his way.

 (33:20)


ACT II – Wine Country

SEQUENCE THREE

Introduce Sub-Plot: Jack isn’t interested in hanging out with Miles or learning anything about wine; he just wants to pick up as many women as possible.

Introduce Supporting Character(Lover): The object of Jack’s affection Stephanie, party girl and winery employee.

Act II Obstacle: Stephanie arranges a double date between the foursome. Miles is nervous to start dating again.

Establish Act II Main Tension: Miles wants to take Jack Wine Tasting, and Jack has no interest in wine. Jack wants to get laid, but he doesn’t want Stephanie to find out that he’s engaged.

Raise the Stakes: Jack reveals that Miles’s ex-wife Victoria has just gotten re-married, devastating Miles.

Rising Action: During the date, Miles drunk dials his wife.Stephanie suggests that they all go back to her place. (00:48:20)

SEQUENCE FOUR

Plant: Miles has a bottle of 61’ Chateau Cheval Blanc (A very rare, well regarded bottle of wine) The bottle is peaking right now, and he was saving it for his wedding anniversary. Maya says he should drink it before it’s too late.

Midpoint (Plot Point #3):At the conclusion of their double date, Jack and Stephanie sleep together while Miles misses his opportunity with Maya. Like the 61’ Chateau Cheval Blanc, he waits too long to make his move.

Plant: Maya wants to read Miles’s novel. He gives her the huge manuscript.

(01:02:38)


SEQUENCE FIVE

New Act II Obstacle: Prevent Jack’s fiancé from finding out about the affair with Stephanie.

Sub-Plot Revival: Jack’s fiancé has been calling and wondering why he hasn’t checked in.

Protagonist’s Objective Ramifications: Jack ditches Miles to spend time with Stephanie.

Boredom Montage: Miles wastes time at the hotel, grades some English papers, checks messages about his book, eats, golfs, etc.

Predicament: Miles comes back to the hotel room and discovers Jack and Stephanie having sex.  Jack is thinking of calling off the wedding.

New Protagonist’s Objective: Re-kindle an opportunity with Maya.

Predicament Obstacle: After going to the Hitching Post to find Maya, Miles discovers she’s off and gets drunk by himself.

Action Block: Miles and Jack almost get into a fight on the golf course, but instead they attack some golfers who try and play through on them by hitting a ball toward them.

Reveal: Miles admits that he’s very nervous that Maya will find out that he’s not actually a published author.

Raise the Stakes: The four go on a double date again: wine tasting.

Obstacle Solution: Miles finally makes a move on Maya and they spend the night together.

(01:23:50)


SEQUENCE SIX

Higher Act II Obstacle & Sub-Plot Obstacle: Miles accidentally reveals to Maya that Jack is engaged. Miles pours his heart out to Maya, but she’s too mad at him.

Rising Action: After finding out his book isn’t getting published, Miles flips out and drinks way to much wine at the winery.

Sub-Plot Obstacle Ramifications: Stephanie confronts Jack and breaks his nose after finding out he’s engaged.

Reveal: Miles calls Maya and leaves a long heartfelt message on her answering machine, telling her everything.

Rising Action: Jack starts to put the pieces together and is trying to figure out how Stephanie figured it out, Miles lies, and Jack’s skeptical.

Highest Act II Obstacle: Jack doesn’t know how he’s going to explain the broken nose to his fiancé. Miles knows he’s really blown his chance with Maya.

Plant: Jack asks Miles what his broken nose looks like; Miles replies that it looks like he got in a car accident.

Main Culmination (Plot Point #4): After Jack ditches Miles again to stay late and sleep with a chubby waitress, he shows up at the hotel room naked after being caught by her husband. Jack left his wallet behind, and begs Miles to go back and get it because it has his wedding rings inside.  (1:45:11)

Action Block: Miles sneaks into the house and find Jack’s wallet. The chubby waitress and her husband are having sex. After Miles runs into the room and snatches the wallet, the naked husband chases Miles and Jack’s car down the street.

(1:49:23)


ACT III – Heading Back Home

SEQUENCE SEVEN

Predicament Solution & Payoff: Jack and Miles head home, and Jack begs Miles to drive. Miles lets him, and Jack promptly crashes the car into a tree on purpose.

Sub-Plot Resolution: Jack gets married.

Third Act Twist (Plot Point #5): Mile’s ex-wife Vickie shows up at Jack’s wedding and reveals that she’s pregnant with her new husband.  Miles skips the reception and stops in a burger joint to drink his rare bottle of wine out of a Styrofoam cup.

(1:59:22)


SEQUENCE EIGHT

The Last Obstacle: Miles is depressed without Maya. He sits in English classroom looking incredibly forlorn.

Obstacle Solution & Payoff: Miles gets a message on his answering machine from Maya. She read his book and loved it. She misses him.

Resolution: Miles drives up to Wine Country to see Maya. He knocks on her door.

New Status Quo: Miles is finally ready to start a new chapter in his life.

(2:06:26)