1. Wristcutters: A Love Story (2006)
The ragged chemistry between Patrick Fugit (Almost Famous) and Shannyn Sossamon (A Knight’s Tale) keeps this backdoor romantic comedy breezy — no small feat, considering its title. The movie is just dark enough to woo the cynical half of any sweetheart couple searching for something between The Notebook and Blue Velvet. —Kyle Anderson
2. Wendy and Lucy (2008)
A girl (Michelle Williams) with nothing to her name besides a no-good car and a faithful dog must travel from Oregon to Alaska to find work. Director KellyReichardt (Old Joy) says more about the precariousness of life on America’s margins than any politician will ever pretend to understand. And in a career defined by her subtle, pained grace, Williams delivers her most heartrending work yet. —Karen Valby
3. Walking and Talking (1996)
Writer-director Nicole Holofcener’s debut film about a pair of twentysomething best friends(Catherine Keener and Anne Heche in their breakout roles) dealing with love, heartache, and the bumpy road to adulthood has everything you look for in romantic comedy and rarely find: whip-smart dialogue, bracing honesty, and spot-on performances. When people wax nostalgic about the ’90s heyday of indie film, this is the sort of movie they’re talking about. —Josh Rottenberg
4. Two Family House (2000)
A wisecracking Staten Island native (MichaelRispoli) can’t get the pregnant Irishwoman (Kelly MacDonald) squatting in his newly acquired apartment to vacate, but when he provides her with new housing, her feelings start to change. MacDonald expertly conveys the transition from prickly to smitten, and Rispoli exudes an innocent dreamer’s charm. —Grady Smith
5. Together (2000)
It’s easy to turn people who live on communes into ponytail-wearing hippie caricatures (see: Wanderlust). But director Lukas Moodysson’s bittersweet dramedy (featuring Michael Nyqvist, who’d play Mikael Blomkvist in the Swedish adaptation of The Girl With the Dragon Tattoo) pulls off something more difficult and rewarding, finding the beautifully messy humanity in the screwed-up residents of a 1970s Stockholm commune. —Josh Rottenberg
6. Surfwise (2007)
Nine siblings (two champion surfers, two members of ’90s one-hit wonders the Flys, their swimsuit-designer/model sister, and four other bothers) grew up together in a 24-foot RV under the iron fist of a surfing-obsessed father. This unforgettable documentary about the wave-riding clan becomes an exploration of family bonds and the American dream. —Adam Markovitz
7. Smiley Face (2007)
Dude, there’s no one better at playing stoned than Anna Faris. Her immensely likable wastoid character, who’s daft without being dumb, eats a batch of her roommate’s laced cupcakes and gets herself into a series of ridiculous scrapes. The whole goofy trip is a showcase for an actress at the top of her game who deserves more movies this fresh and funny. —Karen Valby
8. Safe Men (1998)
Two incompetent singers (Steve Zahn and Sam Rockwell) are mistaken for expert safecrackers in Providence. The supporting cast of lunatics — including a disconsolate Mark Ruffalo and Paul Giamatti as a Jewish gangster — keep the madcap story spinning, but it’s Zahn and Rockwell who make it hugely entertaining. —Marc Snetiker
9. The Rules of Attraction (2002)
Upon its release, this cheeky adaptation of Bret Easton Ellis’ novel about a group of bored, privileged college kids (led by James Van Der Beek) was known as themovie where Dawson turned devilish. Featuring a cast of rising stars like Jessica Biel and Kate Bosworth, Attraction also boasts a standout performance by Ian Somerhalder as a (literally) bed-hopping bisexual student. —Dave Karger
10. Rescue Dawn (2006)
Actor Christian Bale and director Werner Herzog are both known for going to extremes for their work. Put the two together in this incredible-but-true survival story of a downed combat pilot who escaped a brutal Laotian prison camp during the Vietnam War, and the result is a kind of gonzo art-house Rambo movie, as harrowing as it is thrilling. —Josh Rottenberg