The flames of damnation are replaced with the fumes of gasoline and pizza in writer/director James Hilger’s netherworld indie Sleepyhead. Lillo Fante (Lillo Brancato) likes to bowl in his spare time and loves his pet parrot. At his utility company job, his pissed-off co-workers direct him to go down a maintenance hole. The next thing he knows, Lillo is coming to on the pavement at night with no wallet. He is on the wrong side of the river, which is boiling hot for some reason. A ferryman in a flashing skull mask (Joseph Vincent Gay) agrees to take him across, but only if Lillo sings “Happy Birthday.”
Across the river, nothing makes sense at first. Lillo gets thrown out of corner markets and accosted by all sorts of strange characters. A voice at a fast food drive-thru informs him, “You’re dead. So, want a cheeseburger?” As Lillo makes his way through this strange tri-state area of Hades, he has to bargain with lost souls as he has no money. All he wants is a way out so he can get home and feed his parrot. Lillo is told the price will be a wine bottle with the blood of Jesus in it. So he takes off down the sidewalks of Hell, looking for the best bottle of booze that ever was.
Hilger shot this infernal vision in Yonkers, New York. On the border of the Italian Bronx, it oozes that New York feel like oil and vinegar from a deli hoagie. It is far from any hell, making it an interesting place for the filmmaker to put one. But he makes the most surreal version possible. So Sleepyhead gets a big recommendation for its rich location cinematography by director of photography Waleed Sokkar. The footage delivers one gorgeous slice of mid-century east coast urbanism after another. You would swear you were watching Mean Streets. The lighting is fantastic as well, with impressive stylized colors applied to locations, which is very hard to pull off.

“…Lillo makes his way through this strange tri-state area of Hades…”
There is also a good level of humor maintained throughout. The sequence in the park with the witches is hilarious, particularly when they are raping the tied-up creep. 99% of the time, rape jokes are unwatchable, but this is Hell after all. Most of the scenes seem non-sequential, like they could have been put into the movie in any order. It is to Hilger’s credit to have the overall motivation of Lillo to get back to his parrot drive to the whole thing.
However, the big flaw in Sleepyhead lies in Hilger’s script. He never defines what the main character did to be sent to Hell. I am not disagreeing with the choice of not revealing this. Hilger heeded a good impulse by leaving it up to the viewer’s imagination. When it first comes up with the co-workers commenting on the unnamed messed-up act, the ambiguity worked. However, there is a difference between being ambiguous and being incomplete. Later on, a demon requires a prize from Lillo. He makes the protagonist recount the worst thing he ever did. Then the scene ends with no further follow-up. At least the director could’ve had Lillo tell the demon but not let the viewer access what is said. Just cutting away makes it feel undone.
Also, the ending doesn’t work, and I think Hilger knows it. There seems to be audio dubbed in post-production to try to make the climax make more sense. I got it, but it was a stretch. It should be a lot more clear, especially when it explains why the movie is called Sleepyhead. Overall, Hilger has turned in a decent indie film that most will have a hell of a time with.