The film's version of the Make-A-Wish Foundation assumes that sixteen-year-old Dylan (Sky High star Michael Angarano) is making a cheap, sophomoric joke at their expense just because there are TV cameras around. But Dylan is dead serious about his wish: to spend a weekend alone with supermodel Nikki Sinclair (Sunny Mabrey, star of Species III). Most everyone around him assumes it's an impossible dream and it might have been, if Nikki weren't such a self-destructive drunk that she badly needs a bit of good PR in order to stay gainfully employed.
With her handler Arlene (Gina Gershon), Nikki makes a quick and cynical appearance at Dylan's home for a photo op, leaving him her business card and the futile hope that if he's ever in New York, he can call up her agency and contact her. Undeterred by the coldness of it all, and figuring that he has absolutely nothing to lose given that he's gonna lose everything soon anyway Dylan decides that the trip to New York must happen.
It's such a good high-concept hook for a movie, blending a potentially tragic situation with a comedy and a mildly risqué undertone, that it's a bit of a surprise to see it as an indie release as slick and crowd-pleasing as it plays, you'd expect bigger stars than Cynthia Nixon to be attached (Wyclef Jean shows up as a cabbie, and Michael Rispoli as a weird mystical guy, but that's about it for familiar faces). Conversely, one might expect an indie film to have a slightly grittier take on things. Director Alex Steyermark, whose only previous feature was the disappointing Gina Gershon vehicle Prey for Rock & Roll, gets great performances out of his actors, but he and writer Barry Stringfellow (Sweet Valley High) occasionally kill the mood with overdone spiritual bits in which dead people (either as ghosts or angels; it's never specified) intervene in the proceedings. If you're going to use such a gimmick, either do it big or not at all as is, the silliness detracts from the otherwise grounded characters. Talk of spirituality is certainly a part of dying, but ghost cab drivers aren't.
That said, it's hard not to get pulled into the emotional flow before the movie's done. You know how it must end, of course, as all stories of dying people inevitably do, but Dylan is no saintly cancer-boy begging for your Disney tears. He calls bullshit on talk of God, shares his medical marijuana with friends, needlessly picks fights and has as his principal goal the task of inducing a celebrity to essentially commit statutory rape on him. "If you were ten years older...," she wistfully tells him; "...I'd be dead," he responds.
The less said about a half-baked romance between Dylan's mom (Nixon) and a football player, the better. But let us take a moment to question an item or two that seem dated. To raise money for New York, Dylan and friends collect all the money they have, buy time on public-access TV and auction off his possessions including porno tapes (not DVDs) there. Have they not heard of eBay? We know the movie is set in the present, because it features a Wyclef song that references 9/11. Dylan's a smart kid, even with tumors hurting his brain, so one has to wonder what kind of life his scriptwriter leads.
Still and all, Angarano and Mabrey bring something special to the proceedings, and they make it work. Every laugh is earned, and if you find a tear or two, it's because you feel it, not because you're forced into it.