Billy Crystal added a list of outstanding comic movies to his repertoire during the 1980s and 1990s, in addition to appearances in popular TV shows like Soap, thrusting him into the leading man category. These films cemented his standing as a comedy classic, as well as putting him in the company of other comic legends like Whoopi Goldberg and Robin Williams, who co-hosted HBO’s Comic Relief.
Many of these films have aged well and are worth seeing again, whether for the first time or as a sentimental look back. Here are the top comic performances of Billy Crystal in films.

1. The Princess Bride (1987)

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Director- Rob Reiner

Return to a period when marshes were swamps and men were men. That is, fire swamps. Quicksand and Rodents of Unusual Size abound. Shrieking eels lived in the lagoons. Also, the world’s most beautiful woman was known as… Buttercup? It is, after all, a twisted fairy tale. Fencing, chasing, escapes, and silly accents are all present and correct. Inigo Montoya, for example, has spent his entire life dreaming of locating the six-fingered man who murdered his father. His massive sidekick is Fezzik. And the kvetching miracle man is Max. Blonde Buttercup has a thing for sad stable lad Westley. When he gets kidnap by pirates, the villainous Prince Humperdinck chooses her to be his princess bride. She gets kidnap and he is slain along the way.

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2. Analyse This (1999)

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Director- Harold Ramis

Dr. Ben Sobel, a New York City psychologist, has one more difficulty to cope with after a fender bender with prominent crime lord Paul Vitti. While living in the shadow of his famous psychiatrist father and dealing with many challenges while getting set to remarry. The infamous mobster chooses to pay the good doctor a visit, hell-bent on resolving his deep-seated difficulties before the annual meeting of Big Apple’s Mafia Dons, secretly suffering from terrible anxiety attacks that render him unable of performing what he is best at. Ben now has a two-week deadline to find a viable solution, as his conflicted but deadly patient refuses to accept no for an answer.

3. When Harry Met Sally… (1989)

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Director- Rob Reiner

The successful political consultant Harry Burns and the New York City journalist Sally Albright haven’t found an answer after a decade of unsatisfactory debates and logical arguments on the ever-present subject of whether men and women can be merely friends. Even though they like bantering when they are not squabbling, Harry and Sally persistently refuse to acknowledge that they are the right fit against the backdrop of a strictly platonic friendship punctuated with dramatic love/hate moments. They are still confronted with this difficult ongoing situation after all this time.

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4. Running Scared (2006)

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Director- Wayne Kramer

Joey Gazelle, a gangster, is in charge of disposing of the firearms that killed crooked cops during a narcotics deal between Italian mobsters and African-Americans. Joey, on the other hand, hides the guns in the basement of his house rather than dumping them in the river, and his ten-year-old son Nicky and best buddy Oleg Yugorsky see him doing so. When Oleg’s abusive stepfather Anzor Yugorsky beats up on his mother Mila, Oleg grabs the weapon from the basement and shoots Anzor, then flees with the gun. Throughout the night, Joey, the Russian and Italian mobsters, as well as the crooked cops, pursue the little kid in an attempt to recover the gun and discover who ordered the boy to shoot his stepfather.

5. Throw Momma From The Train (1987)

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Director- Danny DeVito

Larry Donner is a published novelist and a writing professor who mentors aspiring authors. Larry’s life has turned into a living hell after his ex-wife Margaret published and profited from a book he wrote under her name. One of Larry’s students, Owen Lift, offers Larry the opportunity to kill Margaret in exchange for Larry killing his terrible mother. Larry believes it’s a joke until he discovers Owen murdered his ex-wife. Larry is the main suspect today.

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6. Forget Paris (1995)

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Director- Billy Crystal

A group of friends discuss the narrative of Mickey and Ellen’s relationship with Andy and Liz, a soon-to-be-wed couple, while waiting for their married friends Mickey and Ellen to arrive at a restaurant. The casket gets lost by the airline as NBA referee Mickey travels to Paris to bury his father. The employee entrusted with aiding Mickey is Ellen. The incident pulls them together, but several factors threaten to separate them.

7. City Slickers (1991)

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Director- Ron Underwood

Mitch Robbins, a disgruntled New York City CEO in his forties, is searching for his long-lost grin and a sense of purpose in life. Mitch’s best mates, Ed and Phil, are equally bored. To avoid the dreaded midlife crisis, the long-time friends have chosen to trust their instincts and try their luck at achieving a sense of success this year. Now, the completely unprepared thrill-seekers are pretending to be cowhands on a two-week cattle drive from New Mexico to Colorado in search of freedom.

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