After [my father had] seen me in five or six things, he said, "Son, your mother and I really enjoyed your recent film, and I must say that you're a lot like John Wayne." And I said, "How so?" And he said, "Well, you're exactly the same in all your roles." Now, as a modern American actor, that's not what you want to hear. But for a guy who watched John Wayne movies and grew up in Iowa, it's a sterling compliment.
Kat (Debra Messing), planning a return to London for her sister's wedding, discovers that her ex-fiancé will be serving as the best man. In a panic, she hires a male escort (Dermot Mulroney) to stand in as her significant other.
Sarah Hurlihy (Lane), a divorced preschool teacher who has sworn off dating after her bad breakup, finds her family pushing her back into the dating world. Her sister places a personal ad for her, declaring that anyone answering it "must love dogs," despite the fact that Sarah doesn't own a dog herself. When someone intriguing responds to the ad, she decides to borrow Mother Theresa, her brother's dog, and plunge in.
Jack Nicholson stars as Warren Schmidt, a man who is set adrift following retirement and the sudden death of his wife. Uncertain about his future as well as his past, Warren packs up his 30-foot Winnebago to set out on a journey across the Nebraska plains to attend his daughter's (Hope Davis) wedding to a waterbed salesman (Dermot Mulroney). But every step he takes seems wrong, and Warren seems destined to end his life as he lived it: a failure. But along the way, Warren recounts his journey and shares his observations with an unexpected friend - a poor Tanzanian boy he is sponsoring for 73 cents a day. In his long letters to the boy, Warren begins to see himself and the life he has lived with new eyes.
A 28-year-old woman, who years earlier made a pact with her closest male friend that if neither were married in ten years time they would marry one another, now faces the fact that the man is about to marry someone else. He asks her to be his best man and she agrees, planning to go to the ceremony and then break up the couple before they exchange their vows. Instead, she accepts the turn of events and realizes she doesn't need to be married to be happy.
1878 in New Mexico: John Tunstall picks up young gun men from the road to have them work on his ranch, but also to teach them reading and to civilize them. However he's a thorn in the side of the rich rancher Murphy, as he's a competitor in selling cattle. One day he's shot by Murphy's men. Judge Wilson can't do anything, since Sheriff Brady is one of Murphy's men. But attorney Alex persuades him to constitute Tunstall's young friends to Deputies and give them warrants of arrest for the murderers. Instead of arresting them, William Bonney just shoots them down. Soon the 5 guys become famous and William gets the name "Billie the Kid" - but they're also chased by dozens of Murphy's men and the army. The people however honor him as fighter for justice.
