Planes, Trains and Automobiles (1987)
The ultimate odd-couple comedy, this John Hughes classic pairs a high-strung executive (Steve Martin) with an overbearing but good-natured salesman (John Candy) on a disastrous three-day journey home for Thanksgiving. What makes it stick is how it moves
beyond slapstick. One minute you’re howling as their rental car becomes a burnt-out husk, the next you’re hit with a wave of unexpected empathy. The famous scene where Del Griffith quietly defends himself after Neal Page’s cruel monologue is a masterclass in heart. It’s a film about how the most infuriating people can sometimes be the ones you need most, a lesson delivered with both chaotic laughter and profound warmth.
The Princess Bride (1987)
This film shouldn’t work, yet it’s perfect. It's a fairy tale, a parody of a fairy tale, a swashbuckling adventure, and a heartfelt romance all at once. Directed by Rob Reiner, it has everything: giants, swordfights, heroes, villains, and endlessly quotable dialogue. But its real staying power comes from its sincerity. It’s funny without being cynical and romantic without being cheesy. The story, framed by a grandfather reading to his sick grandson, reminds us of the timeless power of a good yarn and the simple, profound joy of a story about 'true love and high adventure'. It’s a comfort movie that feels both classic and clever every single time.
Tootsie (1982)
Dustin Hoffman plays a difficult, unemployed actor who lands a role on a soap opera by pretending to be a woman named Dorothy Michaels. While the premise is pure high-concept comedy gold, the film endures because it’s so much smarter and more soulful than its summary suggests. As Dorothy, Michael becomes a better man, learning firsthand about the indignities and sexism women face daily. The film is packed with sharp, witty dialogue and brilliant performances, but its genius lies in using a farcical situation to explore genuine truths about empathy, identity, and respect. It’s a laugh-out-loud comedy with a surprisingly resonant message that has only gotten more relevant.
Steel Magnolias (1989)
Set in a Louisiana beauty parlor, this film is a testament to the power of female friendship. The cast—Sally Field, Dolly Parton, Shirley MacLaine, Olympia Dukakis, Daryl Hannah, and Julia Roberts—is legendary for a reason. Their banter is fast, funny, and feels utterly real. The film is famous for its whiplash-inducing ability to pivot from gut-busting one-liners to heart-shattering tragedy. Based on a true story, it celebrates the resilience of women who are, as the title suggests, as delicate as magnolias but as tough as steel. It’s a movie you quote with your friends while laughing, and then quote to them for comfort while crying.
When Harry Met Sally... (1989)
Can men and women really be just friends? This film dives into that question over twelve years in the lives of two people who start as wary travel companions and evolve into the best of friends, and maybe more. The script by Nora Ephron is a treasure of witty, observant, and painfully relatable dialogue. The chemistry between Billy Crystal and Meg Ryan is iconic, creating a relationship that feels completely lived-in. It sticks with you because it’s one of the few romantic comedies that feels genuinely romantic and genuinely comedic, all while capturing the messiness, comfort, and terror of falling for your closest friend.
Broadcast News (1987)
Perhaps the most intelligent romantic comedy ever made, 'Broadcast News' is about three people in a TV newsroom: a brilliant, intense producer (Holly Hunter), a sharp, insecure reporter (Albert Brooks), and a handsome, charismatic anchor who represents the rise of style over substance (William Hurt). It’s a razor-sharp satire of the news business and a deeply poignant look at work, ethics, and unrequited love. The love triangle at its center is complex and achingly real, refusing easy answers. It’s a film for anyone who’s ever poured their soul into their work, felt a connection that couldn't quite be, or watched the world change and wondered about their place in it. It's funny, heartbreaking, and unforgettable.
