1. Punch Drunk Love (2002)
Starring: Adam Sandler, Emily Watson
Directed by: Paul Thomas Anderson
Punch Drunk Love is usually classified as a dark comedy, which it most certainly is. Paul Thomas Anderson’s entertaining follow-up to Magnolia is about a very eccentric businessman dealing with crippling loneliness, his 7 invasive sisters, a budding romance, and a phone sex scam in which he is the target of. There are few characters out there as oddly memorable as Barry Egan, and Sandler plays the role quite marvelously.
There’s also a small role played by the late great Phillip Seymour Hoffman, who delivers a performance that demands to be admired:
2. Tiny Furniture (2010)
Starring: Lena Dunham, Laurie Simmons, Alex Karpovsky
Directed by: Lena Dunham
Tiny Furniture is Lena Dunham’s first movie — the thing that Judd Apatow liked so much, he figured he could build an entire HBO television series around the young starlet.
You can see why Apatow saw so much potential in Dunham, as she makes a movie that easily could be terrible (it’s about an aimless postgrad who moves back in with her mom and sister), and turns it into a poignant commentary on familial relationships, personal intimacy, and a slew of other zeitgeisty realities. While that last sentence was primarily bullshit, Tiny Furniture is not.
3. Sleepwalk With Me (2012)
Starring: Mike Birbiglia, Lauren Ambrose
Directed by: Mike Birbiglia
Mike Birbiglia’s debut film, an adaptation of his one-man off Broadway show of the same name, tells the semi-autobiographical story of a stand-up comedian juggling his career, his relationship, and a severe sleepwalking problem. Like most of Birbiglia’s work, it’s equal parts endearing, thought-provoking, and laugh out loud funny.
4. Our Idiot Brother (2011)
Starring: Paul Rudd, Elizabeth Banks, Zooey Deschanel, Emily Mortimer
Directed by: Jesse Peretz
You probably remember the previews for this a few years back, as it’s difficult not to remember Paul Rudd looking like an extra in Bruce Almighty. While Our Idiot Brother was released during one of the most forgettable movie times of the year (this time), I found the movie a rather pleasant surprise; the cast is excellent, and is the rare feel-good comedy that uses a a rather simple plot to execute a pleasant message.
TJ Miller, the now-Silicon Valley star, plays a supporting role here and really steals the show in every scene he’s in.
5. Chasing Amy (1997)
Starring: Ben Affleck, Joey Lauren Adams, Jason Lee
Directed by: Kevin Smith
Like Kevin Smith’s other earlier movies, Chasing Amy is about a very particular subset of young New Jerseyans in the late 90s. The world is portrayed in an impeccably specific manner, which enables the story — a comic book artist falling for another comic book artist, who just so happens to be a lesbian — to really shine through. Like a few other movies on this list, Chasing Amy does an incredible job remixing the traditional rom-com formula.
6. Trading Places (1983)
Starring: Dan Aykroyd, Eddie Murphy
Directed by: John Landis
Trading Places is far from underrated, as it’s widely considered one of the better comedies of the 20th century. The Eddie Murphy/Dan Akroyd movie is on this list because it simply doesn’t deserve to be one of those movies that becomes culturally obsolete a few decades later. Murphy and Akroyd’s performances are amongst the best of their career, and their chemistry is undeniable.
(I hate being the guy who talks about how classic movies are that came out before he was even born, but this is one of those movies that forces you to be that guy.)
7. Bernie (2011)
Starring: Jack Black, Shirley MacLaine, Matthew McConaughey
Directed by: Richard Linklater
This summer, Richard Linklater has been making considerable waves for his coming-of-age epic Boyhood. Prior to Boyhood he made Bernie, based on the true story of Bernie Tiede, a 38 year-old mortician who murdered his partner, an 81 year-old (and incredibly wealthy) woman named Marjorie Nugent. Bernie was so well-respected and beloved within the town of Carthage, Texas, that even though he confessed his murder to the police, the district attorney (played Matthew McConaughey) was forced to institute a change of venue to ensure a fair trial. The movie is as wacky as the bafflingly true story.