Billy didn't take long to get used to performing in full character. They used a luxurious apartment nearby where some scenes were shot, a convenient setup that made rehearsals feel more natural.
The director kept everything on budget, filming in three parts. The first part depicted the characters as completely separate, the second explored their growing awareness—and even dislike—of each other, and the third focused on their reunion. It was a story with many layers to peel back, yet everything began to change from the moment the characters met. The director's method was demanding but effective: she required the actors to spend time together off set—eating meals, playing board games, simply sharing their days—while exchanging notes with her. This made many of the conversations in You've Got Mail feel organic and natural, as if drawn from real life. They often recorded these interactions for fifteen minutes at a time, capturing authentic moments.
—You're terrible at Monopoly. —laughed Winona as she shuffled her money again, her hands moving with the playful energy of a child, while Billy slowly emptied his precious stash.
He chuckled a little. They had been playing for four hours; as often happens, board games that seem simple at first become a battleground when strategy is lacking.
—Let's play chess next time. —Billy sighed.
—I thought we'd play Clue—tracking down villains, playing detective. That sounds fun. —Winona replied cheerfully.
—I'll message you on the computer later. —Billy said.
—All right, I'll look forward to our late-night chat. —Winona answered.
…
The first scenes were scheduled for when the weather was just right. It was a pity that some days lacked color, but today was perfect for filming, just before the chill set in and well in time to capture the glow of spring by March. The movie's story spanned autumn to spring, a period of transformation—ideal for showing the characters' journey.
—It's a new photography technique. These cameras can capture much more elegant panoramas, though they only work for interval shots—every three seconds or so. —Billy explained to John Lindey, who was fascinated by how such lenses could breathe life into a scene or drain it away depending on how the panoramic shots were taken.
—It seems, rather tragically, that I'm getting too old for this kind of work. Still, the image is beautiful. —said John Lindey. Under Lux Animation, they had secured one of the most advanced (and expensive) cameras on the market, a tool that could change filmmaking entirely by offering new perspectives to those eager to see cinema from different angles.
—It can be quite limiting. —Billy remarked.
—Well, I'll speak with Nora about the shots. —John replied.
—Take 2, Scene 2. —
JOE: (continuing to read his letter aloud)… though he likes eating bits of pizza and bagels off the sidewalk, while I prefer buying them. Brinkley's a great catcher; he was even offered a tryout for the Mets' farm team… but he decided to stay with me so he could spend eighteen hours a day sleeping on a huge green cushion the size of a car tire. Don't you just love New York in the fall? Makes me want to buy school supplies.
PATRICIA: Ready?
JOE: Wow!
PATRICIA: Almost ready.
JOE: (letter)… I'd send you a bouquet of freshly sharpened pencils…
PATRICIA: Did you turn it on?
JOE: (letter)… if only I knew your name and address.
PATRICIA: I need a stand-in today.
JOE: (letter) Then again, there's a certain charm in not knowing.
Billy's confident smile, his crisp shirt fitting neatly under the suit, contrasted with the more somber undertones of his role. His grin carried a touch of arrogance, far from the melancholy of the script. Playing opposite such star power—his on-screen father portrayed by the dashing Robert Redford and his grandfather by Kirk Douglas—felt like a privilege. Three generations of iconic actors, each with their own distinctive brilliance.
PATRICIA: Did you push it?
JOE: Yes, yes, I pushed it.
PATRICIA: Well, he was late! Random House fired Dick Atkins—good riddance! Murray Chilton died, so that's one less person I'm not speaking to… Hurry, hurry, hurry! Ugh! Ha! Vince got a glowing review. He's going to be unbearable. Eh, dinner with Pen tonight…
JOE: Should I go?
PATRICIA: Joe Fox, you promised.
JOE: It's black-tie.
PATRICIA: Ugh, mm!
JOE: Can't I just donate the money instead? What is it this week—free Albanian writers?
PATRICIA: Oh, ooooh…!
JOE: I'm in favor.
PATRICIA: Oh, ooooh, ooooh…!
JOE: All right, I'm going! I'm going. You're late.
PATRICIA: I know.
—Cut. —
The dialogue was demanding yet sharp, without unnecessary frills. Billy brought all his skill to breathing life into the role's edgier side, giving it a subtle, lived-in authenticity.
—You've got another take. —someone whispered to Billy, who nodded.
Stepping fully into character, his polished black suit and crisp white shirt fit him like a second skin. He stayed composed, undisturbed by the bustling crew around him.
—Don't worry. My take will have everything it needs. —Billy said, capturing the essence of a character inspired by real-life acquaintances he had studied closely. He delivered an excellent performance.
—All right then, cowboy, let's do it again.
—Take 1, Scene 3. —
COMPUTER: You've got mail. (Brinkley pants)
JOE: You've got mail! (to Brinkley) All right, now go on, go, go, go!
KATHLEEN: (voice of Kathleen, reading her email to Joe) Dear friend, I like to think of myself as already mid-conversation with you. I pretend we've been old friends for years rather than two strangers who met in a chat room we both claimed we'd never been in before. I wonder what NY152 will say today. I log on, wait impatiently for the connection, hold my breath until I hear those three little words: "You've got mail." I hear nothing else, not even the sounds of New York streets—only my own heartbeat. I've got mail. From you.
KATHLEEN: (reading her email) I once read a story about a butterfly in the subway, and today I saw one—it got on at 42nd Street and off at 59th, where I imagine it went to Bloomingdale's to buy a hat that turned out to be a mistake. Like almost every hat.
JOE: (reading his email) Listen to this. Every night, a truck pulls up to the bagel shop in my neighborhood and pumps a ton of flour into underground tanks. Then the air fills with white dust that seems never to settle. Why?
KATHLEEN: (reading her email) Confession: I've read Pride and Prejudice about 200 times. I get lost in the language—words like "there," "wretched," "felicity." I always worry whether Elizabeth and Mr. Darcy will truly end up together… Ah! Read it! I know you'll love it!
JOE: (reading his email) The whole purpose of places like Starbucks is to allow people with no decision-making skills to make six choices just to buy one cup of coffee—short, tall, light, dark, caffeinated, decaf, low-fat, non-fat, and so on. That way, those who have no idea what they're doing—or who they are—can, for $2.95, not just buy a cup of coffee but acquire an identity. Tall! Decaf! Cappuccino!
BARISTA: Tall decaf cappuccino?
—Cut. —
It was a good day's shoot. That morning, they had filmed long walking scenes through the city streets, keeping them open but striving to make them appear clean and vibrant. With these extended shots, there was no need for extra takes.
...