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Best Comedy Movies Alone On A Rainy Night From The 80S And 90S That Will Keep You On The Edge Of Your Seat

These comedy picks were hand-selected for a rainy night in, not pulled from a popularity chart. Every pick is chosen for emotional and situational fit, not streaming popularity or critic scores.

The best comedy movies alone on a rainy night from the 80s and 90s that will keep you on the edge of your seat. Includes The Princess Bride, Knockin' on Heav...

Rain against the window and a film nobody else picked. This is one of the few configurations that actually allows you to pay full attention.

The 80s and 90s are where a lot of cinema's DNA was written. Films that set the templates still running today.

Great comedy is harder than drama. The timing has to be precise, the characters have to be real, and the laughs have to be earned rather than demanded.

The Princess Bride movie poster
1
1987 · ★★★½☆ 7.7/10

In this enchantingly cracked fairy tale, the beautiful Princess Buttercup and the dashing Westley must overcome staggering odds to find happiness amid six-fingered swordsmen, murderous princes, Sicilians and rodents of unusual size. But even death can't stop these true lovebirds from triumphing.

Knockin' on Heaven's Door movie poster
2
1997 · ★★★½☆ 7.7/10

Two young men, Martin and Rudi, both suffering from terminal cancer, get to know each other in a hospital room. They drown their desperation in tequila and decide to take one last trip to the sea. Drunk and still in pajamas they steal the first fancy car they find, a 60's Mercedes convertible. The car happens to belong to a bunch of gangsters, which immediately start to chase it, since it contains more than the pistol Martin finds in the glove box.

Fried Green Tomatoes movie poster
3
1991 · ★★★½☆ 7.7/10

Amidst her own personality crisis, a southern housewife meets an outgoing old woman who tells her the story of Idgie Threadgoode and Ruth Jamison, two young women who experienced hardships and love in 1920s Whistle Stop, Alabama.

Brazil movie poster
4
1985 · ★★★½☆ 7.7/10

Low-level bureaucrat Sam Lowry escapes the monotony of his day-to-day life through a recurring daydream of himself as a virtuous hero saving a beautiful damsel. Investigating a case that led to the wrongful arrest and eventual death of an innocent man instead of wanted terrorist Harry Tuttle, he meets the woman from his daydream, and in trying to help her gets caught in a web of mistaken identities, mindless bureaucracy and lies.

Black Cat, White Cat movie poster
5
1998 · ★★★½☆ 7.7/10

A small-time hustler makes a deal with a notorious gangster to whom he owes money: marry his teenage son to the latter's daughter. However, the young lovers are not as agreeable.

What makes great comedy is specificity. The more precise the observation, the more universal the feeling. These films nail that balance.

Geri's Game movie poster
6
1997 · ★★★½☆ 7.6/10

An aging codger named Geri plays a daylong game of chess in the park against himself. Somehow, he begins losing to his livelier opponent. But just when the game's nearly over, Geri manages to turn the tables.

Groundhog Day movie poster
7
1993 · ★★★½☆ 7.6/10

A cynical TV weatherman, along with his idealistic producer and his sardonic cameraman, is sent to report on Groundhog Day in the small town of Punxsutawney, where he finds himself repeating the same day over and over.

Mediterraneo movie poster
8
1991 · ★★★½☆ 7.6/10

Greek Sea, World War II. An Italian ship leaves a handful of soldiers in a little island; their mission is to spot enemy ships and to hold the island in case of attack. The village of the island seems abandoned and there isn't a single enemy in sight, so the soldiers begin to relax a little. Things change when their ship is hit and destroyed by the enemy, and the soldiers find themselves abandoned there.

I'm Starting from Three movie poster
9
1981 · ★★★½☆ 7.6/10

Gaetano, a young Neapolitan, decides to leave home, work and friends, to look for other moments of life and meet other people.

All About My Mother movie poster
10
1999 · ★★★½☆ 7.6/10

Following the tragic death of her teenage son, Manuela travels from Madrid to Barcelona in an attempt to contact the long-estranged father the boy never knew. She reunites with an old friend, an outspoken transgender sex worker, and befriends a troubled actress and a pregnant, HIV-positive nun.

Tension is a byproduct of investment. You're only on the edge of your seat if the film has made you care first. These do.

These films hold up because they were never just funny. They were precise, human, and true. The laughter was always a byproduct of that.

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