On the day that Hurricane Katrina hits New Orleans, elderly Daisy Williams (nee Fuller) is on her deathbed in a New Orleans hospital. At her side is her adult daughter, Caroline. Daisy asks Caroline to read to her aloud the diary of Daisy's lifelong friend, Benjamin Button. Benjamin's diary recounts his entire extraordinary life, the primary unusual aspect of which was his aging backwards, being diagnosed with several aging diseases at birth and thus given little chance of survival, but who does survive and gets younger with time. Abandoned by his biological father, Thomas Button, after Benjamin's biological mother died in childbirth, Benjamin was raised by Queenie, a black woman and caregiver at a seniors home. Daisy's grandmother was a resident at that home, which is where she first met Benjamin. Although separated through the years, Daisy and Benjamin remain in contact throughout their lives, reconnecting in their forties when in age they finally match up. Some of the revelations in Benjamin's diary are difficult for Caroline to read, especially as it relates to the time past this reconnection between Benjamin and Daisy, when Daisy gets older and Benjamin grows younger into his childhood years.

Sara Goldfarb (Ellen Burstyn) is a retired widow, living in a small apartment. She spends most of her time watching TV, especially a particular self-help show. She has delusions of rising above her current dull existence by being a guest on that show. Her son, Harry (Jared Leto) is a junkie but along with his friend Tyrone (Marlon Wayans) has visions of making it big by becoming a drug dealer. Harry's girlfriend Marion (Jennifer Connelly) could be fashion designer or artist but is swept along in Harry's drug-centric world. Meanwhile Sara has developed an addiction of her own. She desperately wants to lose weight and so goes on a crash course involving popping pills, pills which turn out to be very addictive and harmful to her mental state.

Donnie Darko doesn't get along too well with his family, his teachers, and his classmates; but he does manage to find a sympathetic friend in Gretchen, who agrees to date him. He has a compassionate psychiatrist, who discovers hypnosis is the means to unlock hidden secrets. His other companion may not be a true ally. Donnie has a friend named Frank, a large bunny which only Donnie can see. When an engine falls off a plane and destroys his bedroom, Donnie is not there. Both the event, and Donnie's escape, seem to have been caused by supernatural events.

In Albuquerque, Sheryl Hoover brings her suicidal brother Frank to the breast of her dysfunctional and emotionally bankrupted family. Frank is homosexual, an expert in Proust. He tried to commit suicide when he was rejected by his boyfriend and his great competitor became renowned and recognized as number one in the field of Proust. Sheryl's husband Richard is unsuccessfully trying to sell his self-help and self-improvement technique using nine steps to reach success, but he is actually a complete loser. Her son Dwayne has taken a vow of silence as a follower of Nietzsche and aims to be a jet pilot. Dwayne's grandfather Edwin was sent away from the institution for elders (Sunset Manor) and is addicted in heroin. When her seven-year-old daughter Olive has a chance to dispute the Little Miss Sunshine pageant in Redondo Beach, California, the whole family travels together in their old Volkswagen Type 2 (Kombi) in a funny journey of hope of winning the talent contest and to make a dream come true.

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