- Struggling with drug addiction in modern-day New York City, an artist and his best friend complete a spiritual journey started 140 years earlier on the Underground Railroad.
- Santo, the movie's narrator, tells the viewer he and his friends enjoy getting high. Although he is Caucasian (described as Puerto Rican at one point), he also has dreams where he is a slave who is branded and chased. His brother Benny, who had a different father and has distinctly darker skin, is demanding that Santo come and see their mother who has stage 4 breast cancer. Benny has a job. It's not clear how Santo makes a living.
Santo's friend Hunter, who based on his accent and the color of his skin seems to be African, is a successful artist. His paintings are being shown in galleries and his latest advance is $10,000, though he doesn't seem to be spending the money responsibly. His girlfriend Allie, who is white (though that's not important), feels safe with him though others think she'd be better off with someone else, or that she needs a father figure. It's not that Hunter is mean or anything. He's actually calm most of the time. But he seems to need to be high to get his inspiration, and those who appreciate his work think something is missing. The movie really seems to be more about Hunter than Santo.
On one occasion, Santo and his friends go to Nantucket for a party on a private plane with a professional pilot. And of course they're already high. As Santo explains, this is one of five days straight without sleep for him and the others. About halfway through the movie Santo falls asleep and wakes up 2 days later. This is what is known as "5 Up, 2 Down".
Santo seems to be a talented artist himself, but he doesn't seem to be sharing his talent with the world.
There is cheating going on (in stalls of what appear to be single-gender bathrooms), and what little violence the movie has seems to concern this cheating.
Meanwhile, will Santo and Benny ever reconcile, and will Santo see his mother in time? Will Hunter's career fall apart?
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