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Best Billy Crystal Movies, Ranked – MovieWeb

From Mr. Saturday Night to When Harry Met Sally, these are Billy Crystal’s best movies.
Comedian Billy Crystal is one of the biggest icons of his generation. Born in New York City in 1948, he would ultimately end up at New York University as a film and television major, per Film Journal, studying under the likes of Martin Scorsese while there. After college, Crystal began working in comedy with two of his friends, but eventually found moderate success as a solo performer. He began to rise through the ranks of late-night television shows and the improv scene throughout New York City, but then dipped his hand deeper into the world of television and film.
Crystal's very first role in a movie was in Joan Rivers’ Rabbit Test, but he rose to prominence when he appeared on the sitcom Soap and hosted Saturday Night Live for some time. He continued to have a string of successful roles throughout the 80s and 90s, including The Princess Bride, solidifying his status as one of the most well-known figures of his generation. Recently, in 2022 per The New York Times, Crystal wrapped up a run on Broadway in an adaptation of his movie Mr. Saturday Night, showing how he crosses over mediums to reach audiences. That said, these are his best movies.
Mr. Saturday Night was Crystal’s directorial debut and would be his movie that ultimately found its way to a Broadway stage. He stars as Buddy Young Jr., a stand-up comedian who finds himself catapulted to television fame. This is done with the help of his brother and manager, Stan, who, as a child, helped him with performing for their family. As Buddy starts to hit it big and gets his show, things quickly start to fall apart, showing how such good things can be destroyed in mere moments or by a single phrase uttered, including a brotherly relationship. Crystal would later reprise this role in the Broadway adaptation of the movie.
Released in 2019, Standing Up, Falling Down stars Crystal, Eloise Mumford, and Ben Schwartz. For fans of Crystal’s previous work, the subject may seem familiar: he portrays Marty, a comedian whose career is on the decline. He moves back to Long Island in New York from Los Angeles and finds solace in a dermatologist with alcohol issues. Despite both seeming like failures to those outside of their personal lives, they learn from each other how to stand up to their past and move forward from it. Related: These Are the Best Academy Awards Hosts of All Time
Now a classic film for many Americans who grew up during the late-80s and 90s, The Princess Bride is iconic. Adapted from a novel by William Goldman, it has a story within a story. A grandfather reads a book to his grandson about a woman named Buttercup, who, after falling in love with one of the farmhands, finds tragedy after he is presumed lost at sea. When forced to marry the local prince, things go awry, and she ends up on the adventure of a lifetime. Though now considered one of the greatest movies ever released, The Princess Bride was not originally a success.
Monsters, Inc. is one of the biggest franchises and releases that came out of Pixar in the 2000s. Set in the world of monsters, Mike Wazowski and James P. Sullivan are two monsters that get stuck with a human girl who has somehow managed to sneak into the monster world. As they get to talk to and experience a human for the first time in a context where they aren’t forced to scream, they discover that making the girl laugh generates a lot more energy than her being afraid and screaming. Thus begins a decent story that has a couple of twists and turns, making it solid entertainment for a children’s movie.
Related: Best Dramatic Movies From Funny Comedians
Crystal stars in City Slickers, which was a young Jake Gyllenhaal’s debut in the movie world. A trio of friends goes on all of these grand trips abroad and across the country to escape their problems, as they are living through jobs and relationships that are unfulfilling. When they hatch a plan to head on a two-week cattle drive from New Mexico to Colorado, everything is about to change for these three for the better. Full of humor and learning moments, City Slickers is not one to be missed in Crystal’s filmography.
Released in 1989, When Harry Met Sally… has also become a classic for modern viewers. The romantic comedy features Crystal and Meg Ryan as the titular characters. They meet in Chicago and go through a cross-country drive together to New York City, as Sally is planning to start her journalism career there. Things do not go well on this drive, but this is not the end of their relationship. Across the span of 12 years, they keep running into each other, bouncing between love, hate, and friendship.
Writer, author, critic. Find me at @ashleynassarine

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