Elizabethtown (2005)

Plot: Oregon based Drew Baylor contemplates suicide after his professional world starts to fall apart. A running shoe designer for Mercury Worldwide Shoes owned by the egomaniacal Phil DeVoss, he cost the company close to $1 billion after his latest much hyped running shoe design, the Späsmotica, which was supposed to revolutionize the industry and which just went into mass production and initial distribution, is recalled, the shoe ultimately deemed an utter failure. Drew is fired, with news of the fiasco to hit the public consciousness in a featured article in one week's time. Before he can commit suicide, he learns that his father, Mitch Baylor, has just died of a heart attack while visiting his hometown of Elizabethtown, Kentucky. As the oldest offspring and as his mother, Hollie Baylor, was dependent upon Mitch for everything in life, Drew is assigned to go to Elizabethtown to represent Hollie, his sister Heather Baylor, and his own wishes for Mitch's funeral against Mitch's extended family, who Hollie, Heather and Drew have not seen in years. There is especially bad blood between Hollie and the Baylors because she was the one who stole him away from Elizabethtown to the west coast, and from his Elizabethtown girlfriend Connie to whom he was engaged. Drew plans to go to Elizabethtown to carry out this task before he returns home to continue with his suicide mission. Drew feels overwhelmed in this task as he is seen by the extended Baylor family as the successful one, and he feels he needs to maintain the façade for his mother's sake. To deal with this overwhelming situation, he turns to the one person he feels he can, namely Claire Colburn, the gregarious flight attendant he met on his Louisville inbound flight. Ultimately, Claire may not only help Drew get through the funeral arrangements, but may provide Drew with a different perspective of his life.