When the subject of Generation-X films comes up, everybody remembers the John Hughes classics The Breakfast Club, Sixteen Candles, and Pretty in Pink, and Cameron Crowe’s Say Anything and Singles, and Kevin Smith’s Clerks and Chasing Amy. A more attentive movie buff might also remember Repo Man or Kids or Blue Velvet, or there’s even the possibility that a few of you wandered naively into The Crying Game or Paris is Burning and never have been able to forget what you saw. Or maybe you went out on a limb once or twice back in the ’80s and ’90s and tried to watch those cool new movies people were talking about, like Slacker or Wild At Heart. But there’s much more, so . . . in addition to the first ten I already offered, here are ten more that might have gotten lost in the shuffle.
If you think of Jon Cryer as either teenage loverboy Ducky from Pretty in Pink or as the flunky chiropractor Allen in Two and a Half Men, you probably didn’t pay much attention to him in the years between. This late-’90s indie film, which followed the minor high-school comedy Hiding Out, had Cryer playing a young man who goes with his alcoholic best friend on a day-long quest to find a childhood friend who disappeared. This movie captures and uses the Generation X penchant for randomness and pseudo-intellectualism pretty well. The movie only gets a 5.8/10 rating on IMDb, but it’s a better movie than that.
Paris, Texas (1984)
Directed by Wim Wenders and with a storyline from Sam Shepard, this European movie features indie mainstay Harry Dean Stanton playing Travis Henderson, a man who remerges in his small town after he wandered off four years earlier. His young wife, played by model Natassja Kinski, has left, and his young son has been raised by his brother during that time. Travis wants to reunite his family, so his brother helps him, and it becomes a road movie. Some people say that the end of this film is the greatest movie ending ever.
Arizona Dream (1993)
After Edward Scissorhands and before Benny & Joon and What’s Eating Gilbert Grape?, Johnny Depp starred in this film about a young man who goes to Arizona for his uncle’s wedding— but it won’t be that simple. This movie has a stellar cast: comedian Jerry Lewis, beauties Faye Dunaway and Paulina Porizkova, indie actors Lili Taylor and Vincent Gallo, and character actor Michael J. Pollard. If it’s possible to combine Gen-X floundering, unlikely romance, and the complexities of coming-of-age with halibut in the desert Southwest, this film does it.
Night on Earth (1991)
This movie is centered around taxi cab rides in five major cities around the world, and it tells its story in five vignettes about an array of characters. Back when Bravo! was an arts channel, they used to show movies like this one at random times, between Cirque de Soleil reruns and that documentary about Paganini. This was the first time I remember seeing Roberto Benigni, who seemed so wacky, and with her baseball cap on backwards, Winona Ryder was playing a distinctly different kind of role here. (This film came out in the year between Edward Scissorhands and Bram Stoker’s Dracula.) The movie is short on action, but it’s the conversations that carry it forward.
Stranger than Paradise (1984)
Set in New York City and starring musician John Lurie, who you’d recognize from Wild at Heart or Desperately Seeking Susan, and Richard Edson, who you’d recognize as the garage employee who joy-rides the Ferrari in Ferris Bueller, this is another distinctly Generation X road movie, as two Hungarian cousins leave New York City to visit their aunt in Cleveland. Of course, it goes further than that.
Living in Oblivion (1995)
Self-described as a “film about filmmaking,” this movie is a farce about the making of a low-budget movie. I remember reading about this in Village Voice when I subscribed in the mid-’90s but not actually seeing the movie until later. Of course, the cast is pure ’90s indie: Steve Buscemi, Catherine Keener, Dermot Mulroney, James LeGros . . . and even has Peter Dinklage who later became famous in Game of Thrones. If you find chaos funny, you’ll like this movie. If you don’t, you probably won’t.
Where the Day Takes You (1992)
Another one I saw back when Bravo! showed good movies, Where the Day Takes You tells the story of a group of homeless teenagers in Los Angeles led by a cool dude named King, played by Dermot Mulroney. The movie intersperses its main story with videotaped segments of King talking to a counselor about how he’d like to get off the street. Lara Flynn Boyle plays a new arrival on the scene who, of course, falls in love with King. It’s a pretty bleak movie, but not as bad as some on this list.
Near Dark (1987)
Like The Addiction, this is one of the lesser-known Generation X vampire movies. It is alternately slow-paced creepy and wildly violent. It lacks the Hollywood feel of Lost Boys, which came out the following year, but it’s better than a movie like 1985’s Fright Night, which was pretty hokey. This one has a small-town boy to fall in love with a sultry girl, played by Jenny Wright from The World According to Garp. But she turns out to be a vampire, and her homeless-punk-Winnebago family doesn’t like this new boy hanging around. Her father is played by Lance Henriksen, of Pumpkinhead fame, and her brother by Bill Paxton from Weird Science. The movie gets a little stupid and gory as it goes along, but hey, it’s a 1980s horror movie.
At Close Range (1986)
Set in the late ’70s in rural Pennsylvania, this film has Sean Penn playing Christopher Walken’s son in a crime thriller that is based on a true story. This was also a film that paired Penn on screen with Madonna, who did the movie’s main song, “Live to Tell.” At Close Range is gritty and tough in its portrayal of cold-blooded killers in a crime family that specializes in the theft of farm equipment, but Penn’s character Brad Whitewood, Jr. finds out that he’s in over his head when he and his friends try to get in the same racket.
Less Than Zero (1987)
I don’t know how I made my first list of ten GenX movies without mentioning this one, which was based on a Bret Easton Ellis novel. I remember seeing Less Than Zero when I was a teenager and thinking that LA looked so cool— until Robert Downey, Jr.’s character had to become a gay prostitute to work off his drug debt. Less Than Zero had Jami Gertz the year before she starred in Lost Boys and Andrew McCarthy the year after Pretty in Pink. It also has a killer soundtrack, wacky ’80s fashion, stacked TV sets, and a red 1959 Corvette convertible. It’s probably the most Hollywood of the movies I’ve listed, but because it’s also dark and dated, it doesn’t get as much play these days.