"Adventures in Babysitting" (Chris Columbus, 1987)
An '80s family comedy from Disney (released under their slightly more mature Touchstone Pictures banner), it centers on a babysitter (Elisabeth Shue), who brings her charges with her into the big bad city to rescue her stranded friend (a similarly youthful Penelope Ann Miller). Of course, anything that can go wrong, does go wrong, including car thieves, a very important Playboy magazine, and a towering mechanic (played by Vincent D'Onofrio) who looks uncannily like comic book character/god Thor. The addition of children to the "wild night" formula injects an additional element of wily danger, and it was a structure closely (lovingly) followed by David Gordon Green a couple of years ago with his offbeat studio comedy "The Sitter." While "Adventures in Babysitting" was directed by John Hughes contemporary Chris Columbus and replicates many of the things that made John Hughes movies so successful (including, apparently, it's queasy pseudo-racism and its Chicago setting), with slightly more late-'80s edge, it's not a certifiable classic, but if you're stuck babysitting, there are worse things you could put on.
"From Dusk Till Dawn" (Robert Rodriguez, 1996)
In a kind of warm-up for their horror drive-in double feature "Grindhouse," "From Dusk Till Dawn" is a genre mishmash written by Quentin Tarantino and directed by his BFF Robert Rodriguez, in which a wild night becomes extravagantly wilder when the entire movie becomes something different. It almost feels like Tarantino knew that his initial story, about a pair of murderous outlaw brothers (George Clooney and in an ultimate moment of wish fulfillment, Tarantino himself), knew that he couldn't top the outrageousness of "After Hours" so he said, "Fuck it," and mutated the script halfway through, adding a bunch of Mexican vampires and turning it into an all-out horror romp. For the most part, this ballsy experiment works, with the squishier second half of the movie nicely complementing the more earthbound initial sections (which also include a prolonged kidnapping and several murders), and the extension of the wild night conceit into the realm of the supernatural is something that is too rarely engaged in. It is pretty wild, too, with obvious touchstones like "After Hours" giving way to explicit references to things like John Carpenter's "Assault on Precinct 13" and George Romero's "Dawn of the Dead." In the end, it's all just bloody good fun.
"American Graffiti" (George Lucas, 1973)
Back before "a long time ago in a galaxy far, far away," George Lucas was interested in transporting us to a location far more familiar – America in the summer of 1962 (its famous tagline was "Where were you in '62?"). It follows a typical coming-of-age format (one that another of our "wild night" entries follows – but more on that in a minute), with a group of friends on the cusp of fracture. Most of this has to do with going off to school and all of the feelings that go along with that. Lucas wisely chose to depict the night as a series of vignettes, with an emphasis on dialogue and aimless "cruising" (riding around in cars, not hitting on gay men), which gives ample opportunity to get to know the cast of likable characters (among them: Richard Dreyfuss, Ron Howard, Candy Clark, and Cindy Williams) and allows the wackiness of the night to escalate gradually. "American Graffiti" was a smash both commercially and critically (people forget that it was nominated for Best Picture) and inspired not only its own middling sequel ("More American Graffiti") but also the phenomenally popular television series "Happy Days" (with Howard playing a similar role). Its wild night is unwieldy in a smaller, more human way, which might be why it's so identifiable and emotionally resonant. It's wildness you can relate to.
"Dazed and Confused" (Richard Linklater, 1993)
Enjoying the general conceit of "American Graffiti" but set more than a decade later (1976), Richard Linklater's masterpiece is a coming-of-age fable about growing up and staying young. The film is set, uncannily, on the last day of school – for some this means graduation for college, for others it’s the beginning of the thorny transition from middle school to high school – and there's one big party that everyone is going to attend. Most of the wildness of this lone wild night has to do with hazing and the outrageousness associated with this huge party. Linklater is a filmmaker who is never in a rush, and lets us get to know these characters in this pivotal moment in their lives, always allowing time to linger on outsider oddness, like the character played by Matthew McConaughey who has graduated from high school but still hangs around for the chicks, or dialogue that maybe rambles more than it should. It's staggering the number of actors who were cast in "Dazed and Confused" and went on to bigger and better things (McConaughey, Parker Posey, Milla Jovovich, Eric Stoltz, and Ben Affleck to name a few). Also staggering is that for all it's wooh-party, wild-night atmosphere, it's also absolutely heartbreaking.
"Harold & Kumar Go To White Castle" (Danny Leiner, 2004)
Harold (John Cho) and Kumar (Kal Penn) are a couple of overachieving stoners who really have the munchies – and they want White Castle. In the course of their very crazy, very wild night to acquire said foodstuff, they encounter a backwoods redneck named Freakshow (Christopher Meloni, having the time of his life), are forced to perform surgery, get attacked by a raccoon, smoke weed with a leopard, and have an encounter with a comically exaggerated version of Neil Patrick Harris. While it's probably never going to enter the National Registry of preserved films, "Harold & Kumar Go To White Castle" is a ball of fun, and goes to some very unexpected places, crafting a lovingly rude homage to late-night aimlessness, coming across as equal parts "Dazed and Confused" and back issues of Mad Magazine and the National Lampoon. Penn and Cho, too, make surprisingly solid heroes, like Hope and Crosby lost in a cloud of marijuana smoke.
"Night On Earth" (Jim Jarmusch, 1991)
An international portmanteau, bringing together a great cast working their cinematic passports, there probably few films that will take as many places in just a couple of hours, like Jim Jarmusch's "Night On Earth." Following five cabbies and their passengers -- Winona Ryder driving movie agent Gena Rowlands in L.A.; Armin Muller-Stahl driving Giancarlo Esposito and Rosie Perez in NYC; Isaach De Bankolé driving Beatrice Dalle in Paris; Roberto Benigni driving Paolo Bonacelli in Rome and Matti Pellonpaa driving Kari Vaananen, Sakari Kuosmanen and Tomi Slamela in Helsinki -- at the same point in time, the film motors unvenly with the opening L.A. portion, but shifts into an easy gear for the rest of the running time. The warm and funny New York section is caried by the easy charm of Esposito and Perez, while the genuinely hilarious Rome segment reunites Benigni with Jarmsuch (they paired on "Strangers In Paradise"), with the comic actor in top form. There is a romance and poetry to watching life and the city race by through the windows of a cab (or any car really) that Jarmusch perfectly captures, and the entire effort is aided by songs from Tom Waits. While perhaps not as discussed or admired as other Jarmusch movies, and maybe not as wild as the others on this list, it's no less special, and few nighttime journeys are as memorable as this.