10 Best Billy Crystal Movies, According To Rotten Tomatoes

Billy Crystal is a national treasure and, throughout his long career, has been known for being many things: a comedian, an impressionist, an Oscars host, an author, a storyteller, and above all, an actor. He’s been a part of so many great comedies that have become classics and his expressive abilities have led to a wide range of great comedic characters.

Recently, Crystal released Here Today, a film he wrote and directed. It’s a great reminder of his immense comedic talents and proves there is, quite simply, no one else like them. Being a natural improviser, Crystal is able to add great bits of comedy magic that make every one of his projects better and audiences always know, despite the movie’s quality, Billy Crystal is always “mahvelous” in it!

10 Running Scared (1986) – 57%

It may be hard to believe but there was a brief time Billy Crystal was an action star. In the 1980s, buddy cop movies became popular, especially after the success of 48 Hrs. Running Scared teamed Crystal with actor, and legendary tap dancer, Gregory Hines. The film follows two cops who have to make one more big arrest before they can finally retire.

Despite Crystal’s presence, the movie isn’t all laughs, although Crystal does add some funny one-liners throughout. The movie is set in a dreary Chicago, with the humor taking a backseat to drama while also delivering some great action scenes, including a car chase on an elevated subway track. Running Scared was a moderate success but seems to have been forgotten and overshadowed by the era’s more successful buddy cop movies.

9 Mr. Saturday Night (1992) – 58%

Crystal made his directorial debut with Mr. Saturday Night, the story of an aging comedy legend who’s trying desperately to make a comeback. The movie is a great depiction of a bygone era of comedy, and the pitfalls of trying to make a career last in show business.

While the movie received mixed reviews and was a box office bomb, Mr. Saturday Night is a great outlet for all of Crystal’s comedic talents, such as his acerbic and vivacious wit, and his clear love of show business.

8 Throw Momma From The Train (1987) – 63%

Directed by co-star Danny DeVito, Throw Momma From The Train is a clever black comedy sendup of the classic Alfred Hitchcock film, Strangers On A Train. In the film,  Owen (DeVito) mistakenly believes his writing teacher, Larry, wants to swap murders with him so he “kills” Larry’s ex-wife but now Owen wants Larry to return the deed and kill his overbearing mother.

The movie was a hit, and critics and audiences praised Crytal and DeVito’s chemistry. For playing Owen’s mother, the uniquely voiced Anne Ramsay received an Oscar nomination for Best Supporting Actress.

7 Analyze This (1999) – 69%

After playing a mobster several times on-screen, Robert DeNiro finally took a comedic route with the subject matter for Analyze This, a comedy about an anxiety-plagued gangster who seeks therapy from a reluctant psychiatrist (Crystal). Directed by the late Harold Ramis, Analyze This succeeds due to a smart script, the amazing chemistry between its two leads, and for being a clever satire of the mobster movie genre.

The movie proved to be a big success and started a trend for DeNiro in comedies. A sequel, Analyze That, was released a few years later, and while it did not match the original’s success, commercially or critically, audiences still enjoyed DeNiro and Crystal together.

6 Deconstructing Harry (1997) – 73%

For Deconstructing Harry, Billy Crystal has a small role within Woody Allen’s huge ensemble cast. In the surrealistic film, Allen plays Harry Block, a writer confronted by his stories and the people he hurt who inspired them.

Crystal appears as Larry, the man who Harry’s wife left him for. Later, Harry describes a comically dark story wherein he travels to Hell and meets the Devil, also played by Crystal. The two then proceed to boast about the horrible things they’ve done and argue whose done worse. Crystal shines in a brief role in what is one of Allen’s best films.

5 Standing Up, Falling Down (2020) – 87%

As time has gone on and Crystal has grown older he’s morphed into playing fatherly mentor roles and that’s just what makes Standing Up, Falling Down so great. An independent film starring Ben Schwartz, the movie concerns a failed comedian that moves back home with his parents and learns how to confront his failures after beginning a friendship with a funny but alcoholic dermatologist played by Crystal.

The film premiered at the 2019 Tribeca Film Festival where critics and audiences praised it, especially for the two leads’ chemistry. For Crystal, it was his best-reviewed live-action film in many years.

4 City Slickers (1991) – 90%

One of Billy Crystal’s best films and biggest hits was City Slickers: A western comedy about three inexperienced men taking part in a cattle drive that turns dangerous. Crystal plays Mitch, a man in the middle of a midlife crisis, and the film co-stars classic western actor Jack Palance as Curly, the cattle drive leader who teaches Mitch about life.

On the surface, City Slickers appears to be a fish-out-of-water comedy or western genre spoof but it ultimately becomes poignant, emotional, and contains many themes on aging and death. For his role as Curly, Palance earned an Oscar for Best Supporting Actor. A less successful sequel, City Slickers II: The Legend Of Curly’s Gold was released a few years later.

3 When Harry Met Sally (1989) – 91%

When Harry Met Sally set a new standard for romantic comedies and few have come close to attaining its level of quality. The movie tracks the relationship between two friends and their struggle attempting a romance that might ultimately cost them their friendship.

When Harry Met Sally made stars out of Crystal and Meg Ryan and has become not just a romantic comedy classic but a movie classic in general. Written by Nora Ephron, immensely likable Ryan and Crystal effortlessly perform the clever and sharp interplay and their chemistry has audiences rooting for them until the very end. Notably, the famous “I’ll have what she’s having” line was a suggestion by Crystal.

2 Monsters Inc (2001) – 96%

After turning down the Buzz Lightyear role in Toy Story, a decision he would regret, Billy Crystal took the role of Mike Wazowski in Pixar’s Monsters Inc. Co-starring  John Goodman as Sulley, Monsters Inc takes place in a world powered by the scares monsters give children. However, when a child wanders into their world, it’s up to Mike and Sulley to protect her.

Crystal is perfectly cast as the short, opinionated, and one-eyed green monster, proving turning down Buzz Lightyear was the right decision. Like most Pixar movies, Monsters Inc was a huge commercial and critical success, spawning a sequel, Monsters University, and an upcoming Disney+ series, Monsters At Work, both of which star Crystal.

1 The Princess Bride – 97%

Perhaps Billy Crystal’s most memorable role is actually a small role in The Princess Bride, a fantasy story, and fairy tale, about a pirate (Cary Elwes) who battles many obstacles in order to be reunited with his true love (Robin Wright). In the film, Crystal, buried in old-age makeup, plays Miracle Max, a hilarious medicine man. Interestingly, his big scene was mostly improvised by Crystal.

The Princess Bride was a modest box-office success but, over time, became extremely popular, especially for its many great quotes, including Crystal’s iconic line “Have fun storming the castle!” It’s a great example of taking a brief role and making it so memorable that generations of viewers remember it fondly and quote it for years.

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