Coming out of New York, Billy Crystal began his career as a standup comedian, performing sets at the famous "Improv" and "Catch A Rising Star" stages. His fame took a major bump up when he joined the cast of Saturday Night Live, which more than proved Crystal was born to be performing live on a stage. But he wasn't done exploring all avenues of his comedy career trip. Throughout the 80s and into the 90s, in addition to roles in popular TV shows like Soap, Crystal added to his portfolio a list of quality comedic movies, eventually propelling him into the leading man category. These films helped him hit comedy-legend status, as well as lining him up with other funny giants like Whoopi Goldberg and Robin Williams, who together hosted HBO's Comic Relief, an annual live fundraiser for the world's hunger issue. Plenty of these movies hold up nicely and are worth a watch, whether it be for the first time or a nostalgic look back. To help guide you, here we have best Billy Crystal's best comedic performances in movies, ranked:

RELATED: Billy Crystal on ‘When Harry Met Sally,’ ‘Spinal Tap,’ ‘Standing Up, Falling Down,’ and Drinking Jägerbombs

7. Mickey in Forget Paris

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Image Via Sony Pictures Releasing

In 1995‘s romantic comedy Forget Paris, Billy Crystal not only starred in, but also produced, directed, and co-wrote this film. The movie follows his character, Mickey, who is an NBA referee, literally looking up to all the surrounding players. While traveling to bury his recently deceased father at a World War II funeral site in France, Mickey meets Ellen (Debra Winger) who is working for the very airlines that misplaced the casket. After the funeral, they fall in love, however, their new and budding relationship gets interrupted by life, in general; Mickey needs to head back for the start of the NBA season. From there we see how this fairytale-like love story suddenly switches to reality as the world's demands throw one obstacle after another at Mickey and Ellen. Despite this being a great comedic performance by Crystal, you can see the passion and dedication he puts into the character's dramatic moments. And that makes sense since just about every aspect of this production came from this funny man's brain.

6. Mitch Robbins in City Slickers

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Image Via Columbia Pictures

1991's City Slickers was, for sure, one of the movies that helped propel Billy Crystal towards new heights in his comedic career. This film, a smash hit with moviegoers, follows Mitch (Crystal), a man suddenly dealing with a midlife crisis. Stuck in a joyless job, and searching for his "smile," Mitch's friends Ed (Bruno Kirby) and Phil (Daniel Stern), decide to help by giving him a unique birthday present: a trip to a working cattle ranch where they are to become real cowboys and help drive a herd to another ranch. Soon after starting this experience, the usually controlled journey takes unexpected twists and turns, forcing the three friends to rely on each other more than they’ve ever had to in their lives. With plenty of laughs from not only Crystal but the whole cast, this movie also possesses a ton of heart. Crystal plays his character in a relatable way, taking us on his journey from being stuck in a life rut, to eventually finding that "smile," finally proving that cows provide more than just steak and dairy products.

5. Danny Costanzo in Running Scared

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Image Via Metro-Goldwyn-Mayer

Directed by Peter Hyams (Timecop), Running Scared was released during the time when Hollywood started churning out one buddy cop comedy film after another. In this movie, Danny (Crystal) and Ray (Gregory Hines) are fed up with risking their lives taking down bad guys (essentially being one of the first to announce that they are "getting too old for this s***") and decide to retire to Key West, Florida to open a bar. Though this seems like the perfect happy ending, it's not yet to be, mainly because that would make this a very short movie. It's also because Danny and Ray decide they need to bring down the one criminal that got away before they ride off into the Florida sunset. Crystal gives a performance that is tough and charming at the same time. Based on other roles he's tackled, a small stretch of the imagination is required to believe that this little funny man from New York is one of the precinct's most successful cops, but that’s part of what makes Running Scared so entertaining.

4. Larry Donner in Throw Momma from the Train

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Image Via Orion Pictures

In Throw Momma from the Train, Crystal takes a break away from the normal mainstream genre and steps into the world of dark comedy. He plays Larry, a struggling novelist unable to complete the book he’s been working on for what seems like an eternity. In fact, he hasn’t gotten past the first line. Unable to get over the fact that his ex-wife, Margaret (Kate Mulgrew), has stolen his original idea to reach novelist-fame herself, Larry drudges through his job of being a writers' instructor while hiding his ever-growing rage. But Larry isn’t the only one seeing red. Owen, played by Danny DeVito, who also directed the movie, is a student in Larry's class and is as observant as he is dim. Since he wants his own mother dead, Owen understands what his teacher is going through. This leads to a Hitchcockian proposal: to help each other eliminate the cause of their anger, permanently. Crystal's comedic reactions to Owen and his plan of murdering each other's enemy is hilarious as it is alarming, while we watch his entire world spiral out of control towards capital punishment.

3. Dr. Ben Sobel in Analyze This

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Image Via Warner Bros.

Billy Crystal and comedy go together like organized crime and therapy (according to The Sopranos). And in 1999’s Analyze This, directed by Harold Ramis, the film taps into this mafia taboo of talking out all the feelings. Here, we have Ben Sobel (Crystal) who is said professional analyst, that has taken on a new client, Paul Vitti (Robert De Niro), a mob boss suffering from anxiety and panic attacks: Constantly under the threat of being whacked or pitched can do that to you. Crystal stands out in this film, despite being the straight character to De Niro‘s hilariously vulnerable tough-guy shtick. Crystal's internal battle between performing a doctor's duty and not being part of anything illegal shines through, giving us plenty of chuckles as we take pleasure in this poor guy's predicament.

2. Harry Burns in When Harry Met Sally...

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Image Via Columbia Pictures

Do you remember exactly When Harry Met Sally? It was 1989 and the director was Rob Reiner (Stand By Me). This was the romantic comedy that set the bar for every romantic comedy after it. That was because this movie had all the right ingredients needed to become an everlasting classic. It was the movie that launched Meg Ryan’s (Sleepless in Seattle) career, as well as pushing Crystal to the Hollywood-elite level. In this film, enemies-to-friends Harry (Crystal) and Sally (Ryan), who met whilst leaving college, use each other to gauge the current relationship climate for themselves. However, like plenty of romantic comedies that followed, what they really wanted/needed was right in front of them the whole time. In this film, Crystal hilariously navigates New York in the late 80s (a confusing time when it was perfectly ok to scream in ecstasy in the middle of a family restaurant) dating scene, as his comedy once again blends with the perfect amount of vulnerability.

1. Miracle Max in The Princess Bride

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Image Via 20th Century Fox

There’s no question that Billy Crystal as Miracle Max in 1987's The Princess Bride is one of his greatest comedic performances. In this film, also directed by Rob Reiner, Crystal combines several characters from his past to create this unique, bazillion-year-old, miracle worker who holds a grudge against his past employer, Prince Humperdinck (Chris Sarandon). Not wanting to be bothered by pretty much anything, Miracle Max is quick to reject Inigo Montoya (Many Patinkin) and Fezzik's (Andre the Giant) request to bring Wesley (Cary Elwes) back to life with one of his famous, world-renown miracles. At first, Max wants nothing to do with the offer, that is, until he finds out that a successful miracle could bring misery to the prince. Flanked by his wife, Valarie (Carol Kane), this combo makes for the movie's most hilarious scene. The character of Max feels like he could be Crystal’s grandfather and his portrayal of Max is a miracle performance that stands out from an already great movie.