Elizabethtown (2005)

This one might have been one you missed, but it is certainly worthy of your time. I found it to be quite a good film, with a well character driven storyline. If you enjoy the work of Cameron Crowe, then you will like this one, he directed and also wrote the screenplay for this.

The film has a somber mood towards the beginning, as the leading character Drew Baylor portrayed by Orlando Bloom gets fired from a shoe company that he works for as an industrial designer. His boss Phil Devoss is played by Alec Baldwin. This leads to him losing all sense of purpose in life, and he falls into a deep spiral of depression. Just as he is ready to take his own life, the phone suddenly rings with news of his father’s death back in Elizabethtown.
Drew is elected to take responsibility of the situation, since his mother Hollie Baylor played by Susan Sarandon and his Sister Heather Baylor played by Judy Greer both decide to shrug off anything to do with this, as it was his late father’s last request.

He has a cousin Jessie Baylor played by Paul Schneider who is much different than him; with his view points on life, which helps change his perspective on things. During his travel to Elizabethtown, Kentucky he meets the witty flight attendant Claire Colburn played by Kirsten Dunst they seemingly hit it off and she decides to help him.
There are more characters in this such as: Bruce McGill playing Bill Banyon, Jessica Biel playing Ellen Kishmore, Loudon Wainwright III as Uncle Dale, Gailard Sartain playing Charles Dean, Jed Rees is Chuck Hasboro, Paula Deen plays Aunt Dora, Dan Biggers is Uncle Roy, Alice Marie Crowe plays Aunt Lena, and Tim Devitt is Mitch Baylor.
I recommend this one; it will leave you feeling sad and happy by the end of the film. This will be remembered by the film community as a standout. I hope you enjoy it as much as I did.