When actors and crew people make the leap to directing, they tend to make movies that reflect their backgrounds. Actors gravitate toward the kind of intense, emotional showcases that give them and their collaborators the juicy speeches, scenes, and dramatic moments they are cruelly spared when directed by those whose lives do not revolve around the sacred art of pretending to be other people for money. When writers get the big promotion to director, their emphasis is, quite naturally, on the written word, on dialogue and monologues and preserving the integrity of their own words or someone else’s. Choreographers, cinematographers, and production designers tend to make movies that are elegantly put together and lovely to look at, but a little empty and dramatically inert. As for producers, well, I’ve been writing about pop culture for close to two decades and once spent a weekend at the home of super-producer Robert Evans, and I still cannot, for the life of me, tell you exactly what it is that a producer does, except that it seems to involve a lot of ego, money, manipulation, seduction, dishonesty and cocaine. I suppose when producers become directors, the product represents those obsessions as well.

It should not come as a surprise, then, that when casting directors become director directors, their films are often defined by some really amazing ensembles. A case in point would be Risa Bramon Garcia, the director of the 1999 non-cult classic 200 Cigarettes, which is wholly acceptable hangover viewing on New Year’s Day but had the potential to be infinitely more. Garcia’s career as a casting director almost couldn’t have begun on a more auspicious note: according to IMDB, her first credit was on 1985’s Desperately Seeking Susan, a film that briefly made Madonna a movie star as well as a pop icon. From there, Garcia racked up impressive credits for casting movies like Something Wild (which broke Ray Liotta), Fatal Attraction, Wall Street, True Romance, Natural Born Killers, Twister, and Flirting With Disaster. That is one hell of a record for spotting talent, and on a mere casting level alone, 200 Cigarettes is a goddamned triumph: the film brings together (drumroll please) Dave Chappelle, Courtney Love, Elvis Costello, Ben Affleck, Casey Affleck, Martha Plimpton, Paul Rudd, Janeane Garofalo, Christina Ricci, Jay Mohr, Kate Hudson, Gaby Hoffman, David Johansen and Caleb Carr in one stunningly inconsequential wisp of a movie.

Unfortunately, 200 Cigarettes barely even feels like a movie; it’s more like a 1980s dress-up party special on MTV (whose film division had a hand in this, as it did Dazed & Confused) with a narrative clumsily shoehorned in. Despite its period setting, in terms of cast, tone and sensibility, the film could not be more a product of its time. Honestly, if Daria and My So Called Life somehow achieved sentience and co-hosted 120 Minutes, the results wouldn’t feel more 1990s than 200 Cigarettes, or more MTV.

“The only thing keeping it from being a cultural touchstone and beloved cult classic is that it is no good at all.”

Wikipedia calls the film “a mosaic”, which is a pretentious way of saying it is a project with a bunch of different stories you don’t care about. In a deliberate nod to American Graffiti and Dazed & Confused, it follows a broad cross-section of lovelorn or just plain horny twenty-somethings as they try to find love or hook up by the time the clock strikes midnight. Though I would argue its cast is on par with those two films, which is no faint praise, as they are easily two of the best cast films of all time, 200 Cigarettes falls short in every other respect.

It has a fun premise and a neat retro setting — New York in the early 1980s — and, like so many of the films I’m covering for this column, it benefits from a sort of double nostalgia, since the gap between today and when the film was released (about sixteen years) is roughly the same as the time between when it was made and when it’s set. Unfortunately, 200 Cigarettes fails as both a 1980s and a 1990s nostalgia movie, although not because it doesn’t pander hard enough. Yes, the only thing keeping it from being a cultural touchstone and beloved cult classic is that it is no good at all. Of course, no movie with a young Dave Chappelle and Paul Rudd can be completely worthless, but given the talent assembled, it’s almost impressive how little the filmmakers were able to accomplish.

The film’s multiple vignettes are connected by Chappelle’s cabbie character, a funky-fresh amalgam of Rick James, Bootsy Collins and Chappelle’s own persona whose cab serves as a disco on wheels, a mobile blast of 1970s love vibes liberally laced with marijuana smoke and advice of varying levels of quality. He ferries many of the film’s characters, including an adorably rage-filled young man played by Rudd who has just been dumped by girlfriend Janeane Garofalo and is drowning his sorrows in booze and contemplating best friend Courtney Love’s offer to be his New Year’s Eve fling. Could these friends actually be soul mates in disguise? Could friendship lead to love? If decades of romantic comedy tradition are any indication, the answer is yes, and 200 Cigarettes is nothing if not a slave to conventions of all sorts.

Kate Hudson shows up as a lovable klutz who loses her virginity to a cad played by Jay Mohr and then follows him around like a lost, crying puppy in a debutante’s sad little party dress. If 200 Cigarettes were a smarter or more self-aware movie, Hudson’s character might have come across as an inspired caricature of a familiar romantic comedy archetype, the gorgeous woman whose beauty is undercut by her inability to master even the most basic of social and societal functions. Instead, the character’s a groaning cliche. At least give this subplot credit for succinctness; it’s a dreadful two-hour romantic comedy about mismatched lovers condensed into a 15 minute subplot begging for the cutting room floor.

“200 Cigarettes doesn’t have a whole lot more to offer than glimpses of how adorable Paul Rudd was when he was younger.”

Other subplots begging to be cut include one about a pair of sentient Long Island accents (played by Christina Ricci and Gaby Hoffman in performances designed exclusively to please their dialect coaches) who are on the hunt for big city romance with rockers and have to make do with a pair of scruffy roadies (Guillermo Diaz and a young Casey Affleck) who have the carefully cultivated scuzziness of punk rockers and the interiors of nice young men, as well as a bartender played by Ben Affleck who comes between a pair of competitive friends.

The disparate stories are also linked by a party thrown by Martha Plimpton, who drinks herself into a blackout worrying that no one will come to her soiree and deals with the sexual insecurities of an ex-boyfriend played by Brian McCardie. Like real-life New Year’s Eves, 200 Cigarettes is an orgy of disappointment for its characters as they struggle and fail to hook up with the people they think they want, and end up with whoever’s around. Conveniently, a film-ending photo montage narrated by Chappelle reveals that after Plimpton’s character passed out drunk, everyone came to her party, had a blast, and ended up hooking up, including Garofalo and Elvis Costello (playing himself) in what I imagine is some nerd’s nerdiest sexual fantasy.

200 Cigarettes is quintessential Yearbook Cinema: much — if not most — of the fun and excitement comes from the weak little rush that comes with seeing familiar faces before they became familiar, in seeing a coterie of big names from across the pop culture spectrum at a time when their careers were, for the most part, still young. The problem is that 200 Cigarettes doesn’t have a whole lot more to offer than glimpses of how adorable Paul Rudd was when he was younger.

Time has made a remarkable cast even more impressive, but during Courtney Love, Paul Rudd and Dave Chappelle’s one scene together all I could think about was Gene Siskel’s oft-noted comment about how frustrating it is to see movies where simply watching the cast eat together would almost assuredly be more entertaining than what they’re doing onscreen. I think it’s safe to assume that even if they were discussing the relative quality of anti-fungal ointments, or comparing their retirement plans, a real-life conversation between Rudd, Love and Chappelle would by definition have to be more compelling than their scene here.

But even in this comic wasteland, which aspires only to slick mediocrity and fails to realize even its modest ambitions, Chappelle is a consistent delight, even if the film doesn’t really seem to have any idea what to do with him beyond putting the camera on him and letting him go. Part of what makes him such a joy to watch is the palpable, infectious joy he takes in his own gifts, in that sheepish, little boy grin he sports when he’s getting high off his own irreverent genius. While everyone else is working overtime to breathe life into cardboard characters and a stale script, Chappelle is clearly having a blast, acting in a movie of his own that just happens to overlap with the one occupied by all of these lesser performers. It’s as if he’s in a high school band where everyone is trying to figure out simple chords while he’s bashing out a crazy Buddy Rich solo on the drums, arms flailing wildly, eyes ablaze with fiery intensity as he gets lost in a stoned frenzy of self-delight.

“Chappelle is a consistent delight, even if the film doesn’t really seem to have any idea what to do with him.”

Chappelle’s cabbie fits the parameters of the Magical Negro, a smiling yet sassy black man who shows up and imparts casual life lessons to the uptight, neurotic people in his cab. But he turns the archetype on its head by establishing in no uncertain terms that for all of his chill-ass counsel, he’s really only concerned with getting high, getting laid, and amusing himself. He’s not there for the benefit of these uptight white people; they’re there to amuse him, to give him something to play off until his shift is over.

In its own unfortunate fashion, 200 Cigarettes is all too faithful to the intense emotions of New Year’s Eve. From the outset, it radiates potential and excitement; the possibilities are limitless. In theory, it is a magical time, a time of romance and optimism and bittersweet nostalgia for the year that passed, a time when people might find their soulmates before the clock strikes midnight or make memories that will last a lifetime. In actuality, New Year’s Eve is more often a time when people force themselves to wear fancy clothes they find uncomfortable and out of character so they can go to a party and make agonizing small talk with people they don’t enjoy anywhere near as much as they’re supposed to, all the while wishing they were at home in bed and that all of the nonsense and hype was over. In that respect, the film is remarkably true to life; it’s filled with characters and actors you imagine you’ll love spending a fizzy 90 or so minutes with, but who almost instantly wear out their welcome, with the exception of Chappelle and Rudd.

New Year’s Eve is a time for memory and anticipation, and 200 Cigarettes unwittingly captures that for most people, those memories consist primarily of how consistently New Year’s Eve has sucked, despite their fervent plans and desires, and that anticipation revolves around how this upcoming year will probably suck too. Also like the typical New Year’s Eve, enjoyment of 200 Cigarettes is dependent on lowering expectations until they’re borderline non-existent, and in convincing yourself that you’re having a much better time than you actually are. Instead of commenting satirically on the inevitable disappointment engendered by this flashiest of holidays, 200 Cigarettes just ends up reproducing that disappointment in breezy but eminently forgettable and skippable cinematic form.

Original Certification: Rotten

Tomatometer: 28 percent

Re-Certification: Rotten

Follow Nathan Rabin on Twitter: @NathanRabin