Tootsie (1982)

It’s as relevant as ever when a man walks a mile in women’s shoes. Michael Dorsey’s a struggling actor who’s fed up with getting turned down for roles so he dresses as a woman to audition for a part on a soap. “Dorothy Michaels” lands it thanks to a pseudo feminist tirade projected at the chauvenist director. Michael becomes so convincing, even he buys into his own hype; his new-found empathy prompts “Dorothy” to insist women everywhere need his advice to stand up for themselves.

One, Two, Three (1961)

Don’t say I didn’t warn you: crisscrossed boisterous action and frenetic dialogue at breakneck speed are not for the faint of heart!

Mac, a driven Coca-Cola exec assigned to West Berlin is desperate to advance, which will ensure relocation to a better city, though he doesn’t share his wife’s preference. He agrees to host his boss’ teenage daughter, who turns out to be impudent and headstrong. Her antics, along with Mac’s priorities, further strain his troubled marriage.

Already juggling a mistress and business negotiations with some reluctant Russians, Mac finds himself the ringmaster of his own circus when the young socialite disappears. Then turns up married. To a Communist. And her parents announce they’re on their way to retrieve her. With only 24 hours to turn a Red beatnick activist into a Blue blooded Count, everyone springs into action to save the day (and thus their own skins).

On a Clear Day (2005)

How “mad” (as they say in Glasgow) does a man have to be to swim the English Channel? Perhaps driven to despondency by long-term grief and strained relationships with his family then pushed to the brink by unexpected job loss. In need of a challenge, such a man sets his mind to accomplishing a crazy goal. Helping their friend achieve it invigorates orhers’ enthusiasm for their own unfulfilled dreams.

Though the premise of a midlife crisis isn’t original, the interwoven private insecurities of the characters make this particular story special unique and their genuine chemistry makes the it feel relatable. Though it’s inevitably predictable, you can’t help but invest in everyone’s personal struggles and thus rejoice in their triumphs.

Marjorie Prime (2017)

Memory is a perhaps the trickiest aspect of the Human Experience. Would technology designed to serve our need for emotional connection (dare I say “closure”?) enhance or hinder the natural process of grief? Far from flashy gadgets integrated into outer space- inspired decor, a glimpse into the not-too-distant future raises intriguing questions about the nature of adaptive technology/ artificial intelligence while challenging our perception of memories. Subtle foreshadowing/ allegory allows the obvious to speak for itself and stunning visuals are almost a distraction but completely appropriate given the main theme.

Caroline? (1990)

That it was originally made for TV by a greeting card company shouldn’t dissuade you from giving this gem a chance. Before Hallmark had an entire channel of cookie-cutter romances, it was the only safe counter to modern political correctness that handles certain topics with patronizing forcefulness. Most movies portray the people they’re suppose to honor as characatures but, refreshingly, this film treats the issue of Special Needs (introduced by a suspiciously convenient long-lost relative, who stands to inherit a hefty sum) with such grace and tact the characters seem to live on after the credits roll.

Coffee and Cigarettes (2003)

That it was likely a vanity project notwithstanding, this quirky movie is truly unique. I can only liken it to an event I attended where we discovered the same guy was in the background of each picture. So we started staging photos to continue the running gag. The final pic of the night was of everyone photobombing him. Similarly, this movie– comprised of a series of casual conversations– features a blend of musicians, actors who typically play minor characters and a few headliners known for their cameos. This time, the titular items (coffee and cigarettes) play supporting roles but by the end they nearly steal the show.

Greta (2018)

Though touted as a “feminist thriller,” more impressive than the casting of all female leads is the originality of the story. To truly thrill, there must be an original premise and genuine plot twists. Nothing kills suspense faster than predictability; fortunately, this movie does not disappoint.

¡Three Amigos! (1986)

Being famous has its perks but at some point the novelty wears off. Still, it’s best to give the people what they want. After all, without fans you’re nobody, which is exactly the position in which three near-broke actors find themselves. Real-life legends are perfectly cast as they bring their natural chemistry and impeccable comedic timing to the roles of former legends of the silver screen, who misunderstood a plea for help from a fan in rural Mexico, who believes they’re the iconic heroes they play in the movies. Desperate for a gig, The Three Amigos arrive in character to a Western-style showdown to face a violent bully, who’s been threatening to take over the tiny village.

Dreamer: Inspired by a True Story (2005)

Yes, an unlikely competitor defies the odds by overcoming a significant injury. However, when it comes to Sonador, his main backer is a child. Though Cale Crane grew up around horses, racing is actually in her blood; the ranch on which she grew up may be empty but it hasn’t seen its last horse, yet. Training a potential champion becomes a family affair, which garners more than luck and money.

Grizzly Man (2005)

A fair & balanced tribute to a quirky guy obsessed with wildlife, especially bears. To some he was a troubled soul seeking purpose; to others he seemed inspirational. To a few he was simply a nuisance. No matter how you regard his passion, there’s no doubt he died doing what he loved: living like a Grizzly.