Comedian Billy Crystal is one of the greatest icons of his generation. Born in New York City in 1948, he would eventually end up at New York University as a film and television major, per newsreel, while there he studied with the likes of Martin Scorsese. After college, Crystal began working in comedy with two of his friends, but eventually found moderate success as a solo artist. He began to rise through the ranks of nighttime television shows and the improv scene throughout New York City, but then dug his hand deeper into the world of television and film.
Crystal’s very first role in a movie was in Joan Rivers’ Rabbit testbut he became famous when he appeared in the sitcom Soap and hosted Saturday Night Live for some time. He continued to play a series of successful roles throughout the 80s and 90s, including: The princess bride, cementing his status as one of the most famous figures of his generation. Recently, in 2022 per The New York TimesCrystal grabbed a run on Broadway in an adaptation of his movie mr. Saturday Night, and shows how he crosses media to reach the public. That said, these are his best movies.
6/6 mr. Saturday Night
mr. Saturday Night was Crystal’s directorial debut and would be his film that eventually made its way to a Broadway stage. He plays Buddy Young Jr., a stand-up comedian who is catapulted to television fame. This happens with the help of his brother and manager, Stan, who helped him perform for their family as a child. As Buddy starts to grow up and get his show, things quickly start to fall apart, showing how such good things can be destroyed in just moments or by a single statement, including a brotherly relationship. Crystal would later reprise this role in the Broadway adaptation of the film.
5/6 get up, fall
Released in 2019, get up, fall stars Crystal, Eloise Mumford and Ben Schwartz. For fans of Crystal’s earlier work, the subject may seem familiar: he portrays Marty, a comedian whose career is on the decline. He moves from Los Angeles back to Long Island, New York, and finds solace with a dermatologist with alcohol problems. Despite both seeming like failures to those outside of their personal lives, they learn from each other how to resist their past and move on from it.
4/6 The princess bride
Now a classic movie for many Americans growing up in the late 80s and 90s, The princess bride is iconic. Adapted from a William Goldman novel, 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 believed to be lost at sea. When she is forced to marry the local prince, things go awry and she finds herself on the adventure of a lifetime. Though now considered one of the greatest films ever released, The princess bride was initially unsuccessful.
3/6 Monsters, Inc.
Monsters, Inc. is one of the biggest franchises and releases to come out of Pixar in the 2000s. Set in the world of monsters, Mike Wazowski and James P. Sullivan are two monsters who get stuck with a human girl who somehow managed to sneak into the monster world. When they can talk to a human for the first time and experience it in a context where they aren’t forced to scream, they discover that making the girl laugh produces much more energy than being scared and screaming. Thus, a decent story starts with a few twists, making it solid entertainment for a children’s movie.
2/6 city people
Crystal stars in city people, which was the debut of a young Jake Gyllenhaal in the film world. A trio of friends make all these big trips abroad and across the country to escape their problems, as they have jobs and relationships that are not satisfying. When they come up with a plan to drive cattle from New Mexico to Colorado for two weeks, everything is about to change for the better for the three of them. Full of humor and learning moments, city people is not to be missed in Crystal’s filmography.
1/6 When Harry Met Sally
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 drive together across the country to New York City, as Sally plans to start her journalism career there. Things aren’t going well on this drive, but this isn’t the end of their relationship. Over the course of 12 years, they continue to run into each other, torn between love, hate and friendship.