The film explores the love triangle of real-life characters Neal Cassady, Jack Kerouac, and Carolyn Cassady in the late 1950s and the 1960s. It chronicles Jack Kerouac writing his seminal novel ''On the Road'', and its effect on their lives.
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An ambitious carnival man with a talent for manipulating people with a few well-chosen words hooks up with a female psychologist who is even more dangerous than he is.
Recently divorced career woman Alex Greville begins a romantic relationship with glamorous mod artist Bob Elkin, fully aware that he's also intimately involved with middle-aged doctor Daniel Hirsh. For both Alex and Daniel, the younger man represents a break with their repressive pasts, and though both know that Bob is seeing both of them, neither is willing to let go of the youth and vitality he brings to their otherwise stable lives.
After he and his first wife separate, journalist David Sheff struggles to help their teenage son, who goes from experimenting with drugs to becoming devastatingly addicted to methamphetamine.
Jon, a first-time filmmaker, finds himself in Lansing, Michigan to present his film at a local film festival. Vince, his high school friend who is now a volunteer fireman and small-time drug dealer, also visits the town to support Jon on his big day, or so it seems. After a raucous hello and much backslapping, it appears that there is an undercurrent of tension in the air.
In the mid-1960s, wealthy debutant Edie Sedgwick meets artist Andy Warhol. She joins Warhol's famous Factory and becomes his muse. Although she seems to have it all, Edie cannot have the love she craves from Andy, and she has an affair with a charismatic musician, who pushes her to seek independence from the artist and the milieu.