The 10 best films of Billy Crystal

As he prepares to host the Academy Awards once more, we chart the movie highlights of Billy Crystal's career...

Billy Crystal

This Sunday will mark the ninth time that Billy Crystal has hosted the Academy Awards, and if he carries on at this pace his hosting appearances will soon catch up with his film appearances. That comment may be a little unfair, but despite being great screen presence and a talented comedian, Billy Crystal has never been a prolific actor, which is a great shame.

Below are what I consider to be some of his finest appearances in film.

10. Analyze This/Analyze That

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These films are perhaps given a hard time as they can be used as an example of where Robert De Niro became a parody of himself, which is partly true. Still, these are far less egregious examples of this than, say, the Meet The… movies.

As it happens, Analyze This is actually enjoyable and turned a decent profit. The sequel? Desperately poor, and barely broke even, if at all. Still, Crystal is perfectly suited to the role psychiatrist Ben Sobel, who as is often the case, is as flawed a human being as the people he treats.

9. Forget Paris

The second of Crystal’s directorial efforts is perhaps not as widely received or revered as some of his key works, but is a strong effort nonetheless (and really quite an underrated little movie).

The fact that the film is incredibly cynical could put a lot of people off, as rather than fall for the usual Hollywood happy ever after trappings of a romantic comedy, it instead deals with a lot of the real problems that exist in relationships once the honeymoon period is over.

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With that in mind it hardly sounds like a barrel of laughs, but there’s plenty of humour to be had. It’s perhaps harsh to compare this to some of the works of Woody Allen, but the influence is clear throughout. The non-linear narrative is an interesting tactic and doesn’t come off as gimmicky; instead it complements the material, as the audience are given pieces of the relationship out of sequence which leaves you guessing as to how things pan out. A fine example of Crystal as a writer, director and star.

8. Howl’s Moving Castle

Not his finest piece of animated voice work (and a film we’d rate higher, were it more of a Crystal project from birth) but his vocal talents are well used in the western dub of Studio Ghibli’s Howl’s Moving Castle.

Whilst not the lead, Calcifer still provides Crystal with ample opportunity to make the character his own, with some damn fine voice work. Perhaps not one of the best films in the Ghibli catalogue. but it still has a hell of a lot of charm.

7. Mr Saturday Night

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Crystal’s directorial debut is a strong effort indeed, and one that oozes class from the start, with a Saul Bass title sequence. Whilst the film was something of a box office disaster, it is one of the more interesting works of Crystal’s career.

The film charts the rise and fall of a stand up comedian Buddy Young Jr., and much of the film requires Crystal to perform under heavy make up to show the aging process of his character. Perhaps inevitably, this is one of the film’s main weaknesses, in that it’s far from realistic and ends up being quite distracting.

Perhaps the reason it performed poorly was down to the fact that it’s not a comedy, which is what you would expect from the subject matter. Instead, Mr Saturday Night is a dark, interesting drama, one very much worth checking out.

6. Deconstructing Harry

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Not necessarily one of the most popular films in Woody Allen’s back catalogue (despite being nominated for three Academy Awards), but I’d argue that 1997’s Deconstructing Harry is one of his underappreciated gems.

Like the Allen-influenced directorial effort Forget Paris that we’ve already discussed, Deconstructing Harry is a film that doesn’t have a traditional narrative. Sure, there’s a key throughline. However, much of the film features flashbacks and scenes depicting the writings of Allen’s character, Harry.

Crystal plays Larry, Harry’s best friend, who has taken up with his wife. And Crystal is excellent here: his chemistry with whoever he shares a screen with really is a treat to behold. He also relishes in playing the Devil, with entertaining results.

5. Throw Momma From the Train

One of Crystal’s first major film roles, Throw Momma From the Train may not be the most sophisticated comedy, but it’s a good time nonetheless.

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Directed by and starring Danny DeVito, this black comedy wasn’t all that well received on original release, although it did bring in some decent box office dollars.

It’s based loosely on Strangers On A Train, something heavily referenced in the film itself. DeVito plays a student of Crystal’s character, and both of them have someone close to them that they would rather live without. So inevitably, a plan to switch killing duties is concocted and hilarity ensues.

Crystal is given practically all of the film’s best lines and consequently steals much of the show, in a performance that perfectly demonstrates the star power that would be seen in later works.

Oh: and Anne Ramsey. She’s just brilliant, isn’t she?

4. City Slickers

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A big box office hit for Crystal back in 1991, City Slickers stands up as a really good, strong comedy, even if its cash-in sequel doesn’t. Parallels can certainly be drawn between City Slickers films and Analyze This, in that both had a first film that hit big, and a sequel that, well, didn’t.

Here, Crystal, along with co-stars Daniel Stern and Bruno Kirby, are great as city types going through a midlife crisis, who are sent to experience life on a ranch. The fish out of water situation enables Crystal to be likeably obnoxious and sarcastic, and his performance nails that perfectly. City Slickers, though, is stolen by Jack Palance, who won an Oscar and a Golden Globe for his performance. Notably, the follow up was nominated for a Razzie.

The sequel is, to be fair, nowhere near as bad as its reputation suggests. The first film? It’s one of the better Hollywood comedies of the 90s. The bit where Palace walks up behind the wise-cracking Crystal remains its highlight: “he’s behind me, isn’t he?”

3. The Princess Bride

The Princess Bride

Granted, I know that this perhaps isn’t technically a Billy Crystal film, and is one that he’s not on the screen for any great length of time, but The Princess Bride is a firm favourite around these parts. And, in the short length of time Crystal is in the film, he leaves a great impression.

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As Miracle Max, Crystal is almost unrecognisable, but is an absolute treat when he’s on screen, and is a major part in one of the most consistently funny scenes in the film. Crystal had worked with director Rob Reiner in another one of his great works, This Is Spinal Tap, prior to this in a small role as a mime artist, and would go on to play a major role in another of the director’s key works. Talking of which…

2. When Harry Met Sally

When Harry Met Sally

Meet Rob Reiner’s follow up to The Princess Bride.

When Harry Met Sally is famed for its deli scene, but has so much more to offer. And like Forget Paris, it’s a rather grown up look at love. The role of Harry, a divorcee adjusting to single life, was based on Reiner’s own experience of that time, and Crystal, a friend of the director’s, was able to bring the right amount of himself to the role. He elevated the material, certainly, and that material was already strong.

When Harry Met Sally is a fine example of Crystal as a movie star, and his chemistry with Meg Ryan is great throughout. In fact, it’s hard to think of anyone, on-screen, that Meg Ryan has ever had a better chemistry with. An outstanding romantic comedy.

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1. Monsters, Inc.

It’s interesting to think that Billy Crystal turned down the opportunity to voice Buzz Lightyear in Toy Story. It’s a decision that Crystal has admitted since that he regrets.

Still, Pixar didn’t hold this against him, and offered him the role of Mike Wazowski in Monsters, Inc., another one of their revered works. While the film doesn’t reach the heights of sophistication of Toy Story, it has a lot of heart and an emotional punch that typifies the studio’s best work.

This is an even better example of Crystal’s talent for voice work than Howl’s Moving Castle as he’s given much more freedom (he’s originating the performance, rather than translating someone else’s), and his chemistry with John Goodman is superb.

While Mike and Sulley may not be Woody and Buzz, they’re still some of the finest characters Pixar have produced, which really is saying something considering the quality in the studio’s catalogue. And a large part of what makes Mike and Sulley such great characters is down to the performances of Crystal and Goodman. Fortunately, we’ll get to enjoy more of their work when Monsters University is released next year…

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