6. Groundhog Day (1993, Harold Ramis)
A Bill Murray tour de force, high in feelgood factor, the idea that you can experience the same day and improve upon it. A little light, a little mindless like some friends.
Full of dark humor, nostalgia, sentimentality, frustration — what we feel when it seems like every day is the same and we wish we could break out of it. That feeling that our friends somehow stay the same but we’re the ones who’ve changed? This is that, in spades.
Add the hilarity of Chris Elliott and elegance of Andie MacDowell. The one-line zingers (“This is a man we’re talking about, right?” Murray says to MacDowell when she describes her ideal mate, a French speaking, poetry-loving, musical instrument-playing, handsome, sensitive, modest, confident, etc.), which are like a secret code among friends, function like inside jokes, and makes us feel warm inside.
7. Clerks (1994, Kevin Smith)
A film about that one friend. Lucky Dante has tough, fearless Randal. Shot in black and white for $27,575 in the convenience and video stores where director Smith worked in real life.
Faux art-house, fiercely independent, it made making a fun, philosophical film far easier than it looked. There’s a brilliant talkiness in the film, especially about sex, like an European film but also distinctly American. And who can’t appreciate the constant refrain of “I’m not even supposed to be working today. It’s my day off.”
8. Bottle Rocket (1996, Wes Anderson)
Anderson expanded his shockingly good 1994 13-minute short film, a Sundance Film Festival entry, into a full-blown film. His funniest, most original film tracks the exploits of three close friends who attempt to pull off a heist under the neighborhood cover of a landscaping company. The Wilson brothers, Owen and Luke’s acting debuts, opposite a perfectly cast, savvy James Cagney as the real criminal.
Great stand-alone scenes and wry dialogue and the naive belief that love overcomes everything — hallmarks of all Wes Anderson films, are ever present. In terms of male friends, you feel sorry for each of them, but importantly, short of feeling too sad. In the end, you love Owen Wilson’s Dignan most of all for dreaming big for himself and his friends, toting his 75 year master plan jotted down in a spiral bound notebook.
9. Y Tu Mama Tambien (2001, Alfonso Cuarón)
A visually stunning, unforgettable, sexed-up story of two smart, but immature Mexican college friends (Diego Luna and Gael Garcia Bernal) who road-trip with an older woman (stunning Maribel Verdu), who’s both mysterious and familiar (the wife of one of the boys’ older cousin).
Part-social commentary, part-erotic drama, part-coming of age story — these are the bonds of a quintessential shared experience that marks friends for life. You will love the epilogue — there’s such truth to what happens to friends who go through something like this and emerge completely changed.
10. Sideways (2004, Alexander Payne)
Based on Rex Pickett’s novel, two friends in their forties, a failed writer/wine aficionado played by Paul Giamatti and a washed up actor played by Thomas Haden Church spend a male-bonding weekend in Santa Barbara wine country to celebrate Church’s upcoming wedding. Virginia Madsen and Sandra Oh co-star as romantic foils, even if you can’t quite buy Madsen and Giamatti as a pair.
A perfect balance of wine talk (why Pinot Noir is good and Merlot is bad, which incredibly caused Merlot sales to dip in California when the movie came out) and middle-aged male wisdom or lack thereof. In the end, friends can only make so you happy, and ultimately, the lesson is you learn to fend for yourself.