Photograph: Andreas Larsson

Talkative and driven, Lavender (above) is from Evanston; Vaughn, from Lake Forest.

The meeting was supposed to seem routine: on the high floor of a glass-walled corporate building, just off Sunset Boulevard in Los Angeles, the two writers were joined by some Hollywood executives to confer with the actor Vince Vaughn. The writers planned to discuss their script for The Golden Tux, a comedy in which, they hoped, Vaughn might play the lead. Because the script was a work in progress, Vaughn was asked not to read it beforehand.

Still, for the writers, it was hard not to consider the implications. Jay Lavender and Jeremy Garelick, fans of Vaughn’s since he starred in Swingers in 1996, were just starting to get some traction in the business, and they had devoted the past year to a gamble, writing a part just for him. Now they couldn’t blow the opportunity. Make a good impression, the writers thought, and then talk business. Besides, they knew they had a chance: Vaughn-who had grown up in Lake Forest-was fresh from some movies that had flopped. Maybe he actually wanted to meet them.

Vaughn arrived last, all six feet five inches of him, and changed the game plan entirely. He sat down and started improvising, riffing on lines and scenes. “Just knowing what the premise was and the character’s name, he started cracking jokes,” Lavender recalls. “In the script, the character’s name is Jimmy Callahan. And there was Jimmy Callahan.”

Despite the high-ranking men beside him, and the fact that the meeting was still, in some way or another, a job interview, Lavender wore a baseball cap and jeans, his uniform since his grammar-school days in Evanston. “I always tell people that I met Michael Jordan when I was a kid,” he says, referring to an encounter at the Evanston Golf Club when Lavender was in junior high. “That took care of everything in terms of being in awe of a person.” And then the Vaughn interview took a dramatic turn. “He pitched us,” Lavender says. “He said, ‘I want to do a movie called The Break-Up, and I want it to be an antiromantic comedy about a couple that breaks up at the start of the movie.'”

That was December 2002. And what a difference a few years can make. Lavender, Garelick, and Vaughn would collaborate to write The Break-Up, then sell the script to Universal Studios for $2.25 million. In early June, the movie opens in theatres in what is already-thanks to Vaughn, his costar Jennifer Aniston, and some serious love gossip-one of the most anticipated débuts of the year. “It was our perfect storm,” Lavender says. With The Break-Up, Lavender, 31, will see one of his scripts turned into a movie for the first time.

“In college, I learned that I should never stop writing, because it’s unlocked a series of doors,” he says. “When Vince walked into that room, we had spent over a year writing something for him. We wrote ourselves into the room. And that’s what I’ve figured out: that I can write myself into the rooms that I want to be in.”

It is early fall, nearly a week since The Break-Up wrapped in Chicago, and Lavender is walking along North Michigan Avenue, heading to a quick lunch in the basement deli of the Seneca Hotel, his home for three and a half months while The Break-Up is shooting. “A lot of people stayed at The Peninsula,” Lavender says. “But it’s expensive. My sister works for me, and I wanted to be able to put her up, too.”

Lavender is tan from a few days of golf and a day at Great America, and he is obviously enjoying his first extended vacation in eight years. After lunch, he will head to Martha’s Vineyard and then Ireland. He is scruffy, wearing a faded Chicago Bears cap, jeans, and a paper-thin blue Nike workout shirt. If he weren’t talking about his role in a multimillion-dollar movie, he could easily be a college kid heading to class. “For an L.A. guy,” says Tom Glynn, a set designer and friend who worked on the film, “Jay flies under the radar.”

On the movie set, Lavender and Garelick worked beside Aniston and Vaughn and the director, Peyton Reed. The writers revised scenes on their laptops throughout the day. Still, it took a few weeks before some set workers realized that Lavender wasn’t a grunt-level employee. “People thought he was a production assistant,” recalls Glynn. “He’s saying hellos to everybody, giving hugs to security guards, getting everyone water.”

At night, after a minimum 12-hour day on the set, Lavender typically went to bed. Toward the end of shooting, even though he doesn’t drink, Lavender hosted a party at McGee’s Tavern in Lincoln Park so he would have at least one chance to see the Chicago friends he had missed.

Studio rules forbid Lavender from disclosing much about the movie before it comes out, so at the Seneca deli he talks about the future-“Our game plan, our design, was that writing would open the door for producing, and producing would open the door for directing”-and picks at a salami and bologna sandwich with a knife and fork.

Lavender is well known as a monumental talker. But at the quiet deli, his voice is muted and his thoughts run in rapid-fire succession. Occasionally, he silences a call on his cell phone, many of them business related. For a screenwriter, there is no better time to get work than when he has signed on to a major project, the buzz is positive, and no box-office report or critic has ruined the run just yet. Suffice it to say, Lavender is a popular guy these days.

For the record (or in case you have not walked past a newsstand recently): Vaughn, already a popular actor, moved to Hollywood’s A-list last spring with the success of the naughty-guy romantic comedy Wedding Crashers. Aniston had already spent seven years in the nation’s living rooms on the TV show Friends, but when her marriage to Brad Pitt dissolved, she became a tabloid obsession-soon joined in the spotlight by her new boyfriend, Vaughn, a romantic entanglement apparently sparked on the set of The Break-Up.

Lavender knows that he has been blessed by association. But his career also testifies to the ambition, drudge work, false starts, talent, and perseverance that it takes to succeed in Hollywood. “Jay has the uncanny ability to stay focused and, no matter what, make it happen,” says the filmmaker Mike Meiners, Lavender’s friend. About nine years ago, as an aspiring moviemaker with an Ivy League degree and two scripts he had written in college, Lavender moved from Chicago to L.A. without a connection or a shred of professional experience. Before he left, friends asked when he might return. Lavender vowed that he would be back someday, and he would be making a movie.

Jay Lavender was born in Albuquerque in 1975, but his Southwestern days didn’t last long. As the family story goes, Lavender’s father, Harold, also known as “Big H,” was a lawyer thinking about switching careers when he visited the Chicago Board of Trade. “Harold called me that night,” his wife, Judith, explains, “and said, ‘I just saw the craziest thing in my life.'” The family eventually settled in Evanston. A second child, Meredith, was born in 1978.

Even as a child, Jay Lavender was a phenomenal talker-capable of exhausting his friends, teachers, his friends’ parents, anyone. “If there’s a word to describe Jay, it’s ‘energetic,'” says Dan Fahner, a longtime friend. “My father used to always say, ‘Oh, OK, Jay, that’ll do.’ He just wouldn’t stop talking.” The boy loved movies, particularly teen draws like Hoosiers and Naked Gun, and he bought movie soundtracks for the films he liked. An avid reader, Lavender says he liked writing, but not any more than he liked to play baseball, soccer, and golf.

He says he wasn’t even fully aware of his writing skills until his senior year in high school at Loyola Academy. One night in late fall, a dean from the Dartmouth College admissions office called the Lavender home and asked to speak with Jay. The call wasn’t to admit the teenager, but the dean wanted to say that he had been reading applicants’ essays for years, and Lavender’s were the best he had ever read. “It was the first time that somebody really made a point of saying ‘keep writing,'” Lavender recalls.

He followed the compliment to Dartmouth, where he played on the golf team and, as a senior, officially started to learn how to write movies. Unlike novels, scripts don’t rely on words so much as images created by the writer. Some writers never acclimate to the terse screenwriting style. But his Dartmouth professor Bill Phillips says that Lavender was a quick study, and one script in particular caught his eye, a story about a New York graffiti artist. Lavender had written the script with a few classmates on a lark, independent of class, but showed it to Phillips anyway. Nine years later, Phillips still remembers his reaction to the work. “If a script is truly wonderful, I’m looking for a visceral reaction,” he says. “Can you make me cry or laugh or scream when I read it? In 15 years of teaching, I’ve come across maybe a half-dozen, at most, that could do that. And I’d put that script in the top half of that half-dozen.”

Eventually, the script received “pass coverage” in Hollywood, Lavender recalls, an elegant term for “close, but no cigar.” Still, he felt confident enough to work the phones, hoping to make some sort of connection. He kept writing and, in the fall of 1997, moved to L.A. “That script started the dominoes,” Lavender says.

That September, Lavender’s best Hollywood contact, an agent’s assistant at Creative Artists Agency who admired his writing, gave Lavender his first Hollywood job: one month of chauffeuring a director of ER for $50 a day. Never mind that Lavender hardly knew the city. “I totally lied about knowing my way around,” he says. Nine months later, that same agent’s assistant told Lavender she was leaving her job at the agency and suggested he interview for her spot. At 23, Lavender was uninterested in the business side of Hollywood, but he felt compelled to meet with her boss, the agent Adam Krentzman. “I told him what I wanted to do: write, produce, and direct,” Lavender remembers. “He said, ‘Well, come work for me and I’ll teach you the business side, and when you can support yourself as a writer, get out of here.'”

Lavender took the job on that condition, figuring he could work and still find time to write. For the next 16 months, he hardly slept. The huge Creative Artists Agency features a roster of powerful executives and scores of eager recent college grads who act as their assistants. For the assistants, the work is often brutal, boring, insulting, or all three, and anyone who complained was told that others would happily take their place. “You’d come back from lunch and some assistant would be gone because they couldn’t take it,” recalls Garelick, who started at Creative Artists shortly after he graduated from Yale.

Lavender typically worked from about eight in the morning to eight at night, answering phones (up to 200 calls a day), typing and reading contracts, drafting memos, scheduling appointments, reading scripts. On most work nights, around nine or ten, he would go home, turn on some music, and write until

3 or 4 a.m. On weekends, he hardly left his apartment. Meanwhile, Garelick was doing about the same thing. The two became fast friends. To keep motivated, they agreed to let each other read the projects they were writing.

By November 1999, Lavender had sold his first script, The Bear and the Bull, a drama about the Chicago Board of Trade. Lavender will not say how much money he got, but the trade journal The Hollywood Reporter put the sum in the “low six figures.” (The movie has yet to be made.) In any case, it allowed Lavender, who had left his job at Creative Artists two weeks earlier, to concentrate on writing full-time. He and Garelick, also on his way to a different industry job, promised to stay in touch.

Two years later, Garelick approached Lavender with what screenwriters like to call a “what if”-a hypothetical situation to get a story idea flowing. In this case, it had to do with a movie about a guy who worked weddings as a professional best man. “From the beginning,” Lavender says, “we wanted to write it for Vince Vaughn.”

The writers set to work, but not everyone was encouraging. “People gave us grief when we wrote it,” Lavender says. “They were like, ‘Oh, Vince Vaughn, the guy from Swingers, whatever.’ They didn’t view him as this star who could open movies at that time.”

A year later, that “what if” became The Golden Tux, and the writers found themselves in that corporate office being pitched by Vaughn himself. “We were, like, ‘Did Vince Vaughn just ask us to write a movie?'” Garelick recalls.

Negotiations, other projects, and the business side of Hollywood would delay The Break-Up for about two years. (The Golden Tux was bought by Dimension Films for a deal in the mid–six figures, though it has not yet been turned into a movie, and Vaughn was cast in another movie about wedding shenanigans, The Wedding Crashers.) Finally, though, Vaughn, Lavender, and Garelick got back together, working feverishly to turn Vaughn’s idea into a screenplay. The trio wrote mostly in the dining room of Vaughn’s Spanish-style L.A. home. Lavender and Garelick worked without pay, and regular schedules were abandoned. “We were on Vince time,” Garelick recalls.

Some days started at six in the morning; others ended around then. “He wanted to get it done so he could shoot over the summer, and we wanted to get it done because we weren’t getting paid,” Garelick says. “We turned down a lot of jobs to do the project, and we were running out of money.” Day and night for about two months, the collaborators sat at Vaughn’s dining room table, the writers with their laptops and Vaughn at the head of the table dictating his ideas. Sometimes, the group would move to the living room and improvise a scene. At quitting time, Lavender, who lived about ten minutes away, would drive home, and Garelick would crash on another friend’s sofa.   Hours later, they would climb over the stone fence surrounding Vaughn’s building, let themselves inside, wake the actor, and start again.

With two of the three writers hailing from the Chicago area, the finished Break- Up script, by Lavender’s account, turned into an ode to the city as much as anything else. The script provoked a bidding war, not least because Vaughn’s star was rising with the success of the comedies Old School and Dodgeball, and with the buzz for Wedding Crashers. Vaughn backed the hope of Garelick and Lavender to see the film through from start to finish and negotiated a role for them as coproducers. “It gave us the opportunity to be on set from call time to wrap every day,” Lavender says. “It also put us in meetings involving casting, production, and marketing that the writers normally wouldn’t have been in.” Vaughn also insisted that the film shoot on location in Chicago, thwarting the studio bean counters.

Today, it is hard to imagine Universal thinking that it got the bad end of the deal. When The Break-Up opens, it will be Vaughn’s first film since the blockbuster Wedding Crashers. It will also have been a year since the romantic saga of Vaughn and Aniston began, with no sign that the pop culture world is losing interest.

Back at the hotel deli, Lavender continues his nonstop account of the dates, names, and details of the past several years-the swirl of Hollywood events that have brought him to The Break-Up. His voice is mellow, but there is still that trademark speedy banter. From a faraway table, his memories might sound like a long hum. “This story begins my senior year,” he says. “That script started the dominoes, and the one thing I learned was never to stop writing. Every time I finished a script, I started another, and so each thing I’ve written has unlocked another series of doors. That’s what I meant when I said I believed I could write myself into rooms.”

I interrupt him with a question about his own hopes for The Break-Up after it makes its début. “I always think it’s premature as a writer to discuss it,” he says. “Because at this point the public hasn’t spoken yet, so we don’t know how well it will be received.” I ask about the buzz surrounding the film, and Lavender is just as terse. “People ask, ‘Is your head spinning?'” he says. “Well, to be honest, I can remember every day it took to get here.”

Put another way, The Break-Up is Lavender’s watershed, and he is clearly tamping down his anticipation. He is also in a tough spot. Lavender is a screenwriter suddenly near the top of his profession, despite the fact that hardly anyone has seen his work. His first movie, a dream realized, is set in his hometown, where scrutiny could get personal. Meanwhile, The Break-Up will have a multimillion-dollar publicity blitz, all but guaranteeing that nothing about the movie, good or bad, will pass quietly.

Several weeks later, after his vacation, Lavender calls on a blustery winter afternoon to say the studio is changing The Break-Up‘s release date, pushing it back from next winter to this June-a summer movie, maybe even a summer blockbuster. You’re charmed, I say. “Honestly,” he says. “We have to have a great movie before anything else.” Lavender’s voice is soft, as if he were describing plans for a casual weekend. And then he changes the subject.