MARCH 31
2004

Variety reported that Susan Sarandon would likely play the part of Hollie Baylor, Drew Baylor’s mother. Other casting possibilities included Judy Greer for the role of Heather (Drew's sister), Jessica Biel for Ellen (ex-girlfriend of Drew's) and Loudon Wainwright III (Uncle Dale). Paula Deen was also in negotiations for a role.
MARCH 22
2004

MTV ran a short piece on Elizabethtown confirming that Orlando Bloom and Kirsten Dunst will officially star in the romantic-comedy.

Cameron was quoted describing their roles and the film in general. "It's about a guy who, on the eve of an incredible fiasco and failure, decides to kill himself," Crowe said. "[But instead,] he takes a trip back to his old hometown in Kentucky and gets broadsided by life. And laughter ensues."

The score for Elizabethtown is being written by Crowe's wife, Nancy Wilson of the band Heart. Wilson co-wrote the songs for the fictional band Stillwater with Crowe in his 2000 movie, Almost Famous. "She'll do all the incidental stuff [for 'Elizabethtown']," Crowe said. "She's really the full-time musician in the family. We wrote some music together for Stillwater, but this one's all her. For the soundtrack, we'll have a lot of great records, which we'll surprise you with down the line."

MARCH 12
2004

According to Variety, DreamWorks will not be co-financing Elizabethtown. Paramount will reportedly distribute the film.
JANUARY 26
2004

Various sources confirmed that Orlando Bloom officially signed on to star in Elizabethtown.

NOVEMBER 7
2003

Ashton Kutcher dropped out of Elizabethtown due to scheduling conflicts.
OCTOBER 27
2003

The Hollywood Reporter warned that film for Elizabethtown had been delayed and Ashton Kutcher's availability was in jeopardy.

Elizabethtown shoot falls back

The start date of Cameron Crowe's Elizabethtown is in flux. Because the director wants to shoot the ensemble comedy during a specific time of year, its original January start date has been pushed to an unspecified spring start, sources said. Because of the date change, the availability of Ashton Kutcher, who is to topline the movie with Kirsten Dunst, is now up in the air. Kutcher's reps confirmed that the actor has such television commitments as Fox's That '70s Show and MTV's Punk'd that could affect his role in Elizabethtown. However, they also said they are working on the situation to see if his schedule can accommodate the change in the film's shooting schedule. Sources also indicated that Crowe is eyeballing Oregon and Kentucky as possible locations for the Paramount Pictures-DreamWorks co-production.” 

AUGUST 22
2003

Cameron released casting information for Elizabethtown on his fansite, cameroncroweonline.com. The lead roles had already been cast for Drew (Ashton Kutcher) and Claire (Kirsten Dunst).

Hollie Baylor: 57 years old, Hollie is Drew's mother. An earthy woman originally from Santa Barbara, she has a restless intellectualism, a brainy "seeker" of truth and knowledge. In many ways, she's an overgrown college girl, a student of life. 

Jessie Baylor: Jessie is Drew’s 31-year-old cousin, and a Kentucky native. A noble almost-success, Jessie is a musician who has not been able to make his dreams pay the rent. Barely making ends meet as a single father, he retains the look and spirit of a musician, though he is now in data processing. Drew loves Southern rock.

Heather: In her late twenties, Heather is Drew's sister. A young suburban mother in a two-income marriage, Heather carries the burden of responsibility. She complains about her misery, though secretly loves it. She is not Southern.

Charles Dean: At 62 years old, Dean is the funeral home proprietor who has become a local institution in Kentucky. A man of great manners and elegant southern diplomacy, his face resembles a natural rock formation. Subtext being his main form of communication, Charles never openly confronts any issue, though his anguished expression shows his true feelings.

Uncle Dale: This Kentucky native is Drew's uncle and Jessie's father, who often finds himself caught between his elder "country" relatives and the energized globalism of the upcoming generation. At 56 years old, Dale Baylor would like to branch out of the south, but it's a bit late for him. He's a noncommittal person, trying to stay current while making the best of his often traditional life and numerous family burdens. His dress of khaki pants and golf-shirt with short hair stands in great contrast to his musician son.

Bill Banyon: Banyon is a mid-level charlatan who left Kentucky for the big city. Bill, 54 years old, is said to be under investigation for tax evasions, though he carries himself like a humanitarian and philanthropist. After running for mayor in three different cities, and losing each time, failure rolls right off him. Bill would be obnoxious if he didn't have such a murky past and wasn't so damn entertaining to watch, the type of guy who would shake your hand and look you in the eye like a brother even when he has just met you and has no idea of who you are.

Ellen Kishmore: Kishmore was once the love of Drew’s life. A great-looking high-level assistant with great style, poise and memorable green eyes, Ellen’s success in business is inexorable. The character is listed as being 24 years old.

Phil: In his forties, he is Drew's boss, a thoughtful billionaire able to speak in long and complex sentences, mesmerizing as he does so. Phil is a father figure to those who work under him.

Chuck: In his early twenties, Chuck is an Asian from Kentucky, about to marry Cindy. He comes across as extremely sweet, with his emotions very close to the surface. Chuck can't help crying when something strikes him as touching, from a beer commercial to the rigors of global warming, or a perfectly folded T-shirt.

Other supporting roles include:

Mitch Baylor: In his mid 50s, he is Drew's father, a fun, likable guy with an open, accessible look, an air of whimsy about him and a Mona Lisa-type smile. Originally came from Kentucky, Mitch later moved West.

David Tan: In his early 30s, he is Taiwan born and speaks English with an accent. David is a computer-geek who speaks with full gesturing of his hands. (It should be noted we will only see the top of his head, never his face.)

Samson Baylor: The 4 years old is Jessie's son and Drew's first cousin, once removed. He is VERY LOUD, with a distinctive howl. When he cries, people in neighboring communities can almost hear it.

There are also calls out for ten other minor roles: Mike Bohannon a professional reporter for a business journal; Debbie, Jessie's girlfriend, who works at a drug store; Charlotte, a type-A personality, memorable for her ability to type expertly at her computer, always dutifully sending information to a database that only she sees; Rusty, a rugged, rustic construction foreman; Cindy an up-scale, athletic blonde, stressed but completely in control of the planning and hosting of her wedding; Ben, who grew up in the South, but now lives in Colorado; Aunt Dora Connelly, Drew's aunt from Kentucky, with a glowing life force of trust and wisdom; Mona, noteworthy for her compelling and poetic stare; Des, an African-American who attended West Point with Drew's father; and Connie, once a girlfriend of Drew's father many years ago.

JULY 10
2003

The Hollywood Reporter stated: 

“Kirsten Dunst and Ashton Kutcher are attached to star in Cameron Crowe's next project, "Elizabethtown” which is slated to begin production in the first quarter of 2004 in Oregon and Kentucky.

“DreamWorks Pictures and Paramount Pictures are in final talks to finance the film, which is being produced by Crowe's Vinyl Films and Tom Cruise's C/W Prods.

"Elizabethtown, which Crowe also wrote, is described as a rich ensemble comedy with two central leads. The project is intended to be a love letter to the resilience of the life force and is a story of an unexpected romance that develops against the backdrop of a Southern patriarch's hilariously elaborate memorial. Like Crowe's previous works, music will figure prominently in the film.

“A portion of the filming will also occur in October before resuming in the new year.”

JUNE 25
2003

Orlando Bloom dismissed rumors that he will appear in Elizabethtown, stating scheduling conflicts and Cameron’s desire to use an “all American” cast would prevent him from playing the lead role.
MAY 30
2003

The Hollywood Reporter stated Kirsten Dunst was in talks with Crowe for the female lead after dropping out of M. Night Shyamalan's next film The Village.

Nancy Wilson (who will score the film) described it as Jerry Maguire meets Say Anything meets Fast Times at Ridgemont High and the best work Cameron's ever done. She also stated that the leads are about twenty-five years old.

JULY-SEPTEMBER
2002

Original start date for Elizabethtown filming. Obviously, it came and went.
JANUARY
2002

During interviews surrounding the Vanilla Sky DVD release, Cameron discussed his upcoming film, Elizabethtown, and described the project as "an ensemble, comedy/drama”.