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31 Greatest Billy Crystal Movies Ranked Worst To Best

With a career that is now in its 6th decade, Billy Crystal has done it all: Movies, television, stand-up, Broadway, and even music, by way of his minor hit novelty song "You Look Marvelous." Though his first big mainstream role was on the sitcom "Soap," most people tend to view "Saturday Night Live" as the place where Crystal really put himself on the path to superstardom. While Crystal was establishing himself as a gifted stand-up and sketch comedy performer, he began taking his film career seriously in the mid-1980s and soon had iconic films like "This Is Spinal Tap," "The Princess Bride," and "When Harry Met Sally" under his belt.

While he would freely move between the various facets of his career over the next few decades — including a recent return to Broadway with the 2022 stage adaptation of his 1992 film "Mr. Saturday Night" — Crystal has largely felt like a movie star above all else. That medium continues to be the one that connects him to the largest audience and has been most directly responsible for introducing him to each new generation of fans. That is the focus of this feature, looking at all 31 of the scripted films in which he has a significant non-cameo role, beginning in the late 1970s all the way through to the present day.

31. SST: Death Flight (1977)

There's something to be said for getting your worst movie out of the way early — your film career has literally nowhere to go but up. In the case of Billy Crystal, the first film he ever appeared in remains his worst by a considerable margin. A made-for-television disaster film that aired on ABC in 1977, Crystal's role in "SST: Death Flight" is admittedly rather small. But since he wasn't famous yet, it certainly wasn't a cameo — so for both that reason and the fact that it's his first ever movie role, it's kicking off this list.

Just how bad is "SST: Death Flight?" Bad enough to be one of the movies featured in the first season of "Mystery Science Theater 3000." There really isn't much to say about "Death Flight" other than how bad it is, and there's nothing especially noteworthy about Crystal's very small role other than the knowledge that the rising star could thankfully afford to become much pickier with his projects not long after this.

30. City Slickers II: The Legend of Curly's Gold (1994)

There aren't very many sequels in Billy Crystal's filmography, largely owing to the types of movies he typically makes. Still, comedies sometimes make enough money that a studio pushes for a follow-up, despite the fact that comedy sequels are almost always a step down in quality from their predecessor. But to call "City Slickers II: The Legend of Curly's Gold" a mere step down in quality from the original is being far too kind. Rather, "City Slickers II" is more like a plummet off a cliff.

With Jack Palance being such a huge part of the original's charm, one of the biggest challenges of the sequel was the fact that his character died before he would have a chance to appear in it. So we meet his identical twin, Duke — and things only get more eye-rolling and hackneyed from there. Crystal does his best with the material, as do Palance and the also-returning Daniel Stern. But "City Slickers II" forgot that the original succeeded on the strength of the characters themselves, and instead focused too much on the adventure aspect — while also not bothering to be a particularly entertaining comedy or adventure movie.

29. Tooth Fairy (2010)

In a tradition that dates back to at least "Kindergarten Cop" and "Mr. Nanny," action heroes often take a break from blowing up bad guys and pile-driving their opponents to star in family-friendly comedies. The muscle-bound leading men of the 2010s were all too keen to revisit this concept, from Vin Diesel in "The Pacifier" to Dwayne Johnson donning wings and playing the titular "Tooth Fairy." 

And, yeah, most of these movies are pretty bad — clearly, these guys just want to take a break and do something fun and less physically demanding, and aren't particularly concerned with the actual quality of the films themselves. To be fair, Johnson is his usual charming self in "Tooth Fairy." But as pointed out by Lucy Barrick of Radio Times, it's the strong supporting cast of seasoned performers like Billy Crystal and Julie Andrews that do most of the work in giving this otherwise forgettable kids' movie a few rare bright spots.

28. Rabbit Test (1978)

"Death Flight" was technically Billy Crystal's first movie, but it was with 1978's "Rabbit Test" that he made his big-screen debut. The sole directing credit of the late, great Joan Rivers — who also co-wrote the script — "Rabbit Test" is a high-concept comedy about a guy (Crystal) who somehow becomes the world's first pregnant man. Critics hated it almost unanimously, with Gary Arnold of the Washington Post saying the movie's attempts at humor "fall flat with dreadful consistency" and Roger Ebert declaring in no uncertain terms that "[Rabbit Test] is not a funny movie. It really isn't."

Still, Rivers believed in it, personally appearing at a number of theaters that were showing the film and helping it to become a financial success in comparison to its cheap production budget. But she never returned to directing, and it was far from being a successful star vehicle for Crystal — he would go back to focusing on television for a few years before trying his hand at Hollywood again. 

27. Parental Guidance (2012)

Though he's made some memorable films in the past few years and seems to be settling into a nice late-career renaissance, Billy Crystal's non-animated film output was largely forgettable in the 2000s and 2010s. There are definitely a few releases in there that feel like they're more about who he was working with rather than what he was working on, and that certainly seems to be the case with family comedy "Parental Guidance."

One can hardly be blamed for not passing on the chance to be Bette Midler's co-lead, and she and Crystal have good chemistry, clearly enjoying themselves. To its credit, there is nothing egregiously bad about "Parental Guidance" and there are far, far worse examples of this type of movie. But it just ends up being completely unremarkable and almost entirely forgotten by the time the end credits are done rolling. It's like if fast food were a movie — it does its job in the moment, but you feel unfulfilled once you're done with it.

26. Memories Of Me (1988)

After spending a decade writing for both television and his own stand-up specials, Billy Crystal wrote his first feature-length movie with the 1988 comedy-drama "Memories of Me." Starring Crystal with Henry Winkler behind the camera in his directorial debut, "Memories of Me" is about Abbie Polin (Crystal), a man who tries to reconnect with his estranged father after he has a heart attack. His father is played by Hollywood veteran Alan King, and JoBeth Williams plays Abbie's love interest. 

The movie itself had largely lukewarm reviews, but praise was given to Crystal's script and performance — particularly his scenes with King. Winkler was also acknowledged for having a creative hand as a director that helped to elevate what is, admittedly, a fairly cliched melodrama a lot of the time. Still, it's a solid effort overall and proved Crystal's writing talents could translate to the big screen — something that isn't necessarily true of even the best television writers. 

25. Breaking Up Is Hard To Do (1979)

While Billy Crystal was taking a break from the big screen after his man-gets-pregnant comedy didn't instantly make him an A-list star, he appeared in a few made-for-TV movies. Luckily, they weren't all as bad as "Death Flight" — and in fact, some were actually pretty decent, especially viewed retrospectively as quirky cult films. "Breaking Up Is Hard To Do" is one such movie, and Paul Mavis of the blog DrunkTV even calls it "a true gem" in a rather extensive write-up on the movie.

A movie about heartbreak and divorce told mostly from the perspective of the men as they try and bond over the experience, "Breaking Up" stars Crystal along with Robert Conrad, Susan Sullivan, and Tony Musante. Considering how little is written about it, it's obvious it didn't make much of an impact when it originally aired on ABC in 1979, even though the cast consisted of a lot of fairly big names in television at the time. But there is definitely some fondness for it out there and some people do remember it, even if it's never going to be anything more than a minor footnote in Crystal's early career.

24. My Giant (1998)

Inspired by the time he spent with André the Giant on the set of "The Princess Bride," per an interview with Bobbie Wygant, Billy Crystal brainstormed some ideas based on stories Andre told him about his life and career. Crystal would eventually team with screenwriter David Seltzer on the script that became the 1998 comedy "My Giant." As André had already passed away by then, Crystal needed a suitable stand-in to play the part of the titular giant — and found him in 7 foot, 7 inch NBA player Georghe Mureșan.

While "My Giant" is both novel and funny in its early scenes where Crystal's character meets the giant in his quaint Romanian village, it becomes a somewhat formulaic showbiz tale in its latter half. It doesn't help that Mureșan is difficult to understand, owing in large part to his very thick Romanian accent and lack of professional acting experience. That isn't his fault, of course, but it doesn't make his dialogue any easier to follow. But he still has a very affable and charming presence, and he and Crystal make for a fun on-screen duo — it's just too bad the movie wasn't more about Crystal's character being the fish out of water rather than the reverse, as those are the best segments of the movie. 

23. Enola Gay: The Men, the Mission, the Atomic Bomb (1980)

Despite his reputation as a comedic actor, many of Billy Crystal's earliest film roles largely skewed dramatic. It's unclear if he was just taking whatever roles he could get, or if there was a conscious effort on his part to be a serious actor — but it's an interesting aspect of the beginning of his acting journey. In the 1980 NBC made-for-TV movie "Enola Gay: The Men, the Mission, the Atomic Bomb," Crystal tackles especially heavy material as he stars in a movie revolving around the United States dropping an atomic bomb on Hiroshima during WWII.

In "Enola Gay," Crystal plays Lt. Jacob Bessler, who has the unfortunate distinction of being the only person to be part of both missions where the U.S. dropped atomic bombs. The production values are pretty decent for a primetime network movie of the time, and Crystal definitely shows that he has acting chops outside of being the funny guy. But beyond that, there's a reason it's mostly been lost to time: It's the kind of TV movie that wasn't really meant to be thought about or discussed long after the week it aired. 

22. Analyze That (2002)

Another Billy Crystal comedy sequel, and another that is squarely in the lower half of this list. "Analyze That" isn't nearly as dreadful as "City Slickers II," but it's definitely an entirely unnecessary sequel to a surprisingly good original. The biggest issue is that the entire gimmick of a dangerous mob boss needing to see a psychiatrist because of his frequent panic attacks is really a one-movie kind of premise, and trying to stretch it into a sequel sees it worn entirely too thin.

It's one of the all-too-common examples of a comedy sequel largely being a rehash of the original, but there is still some fun to be had. Crystal and Robert De Niro have some of the best nervous guy/crime boss comedic chemistry this side of Matthew Perry and Bruce Willis in "The Whole Nine Yards" — and to the credit of "Analyze That," it never feels nearly as dull or vapid as the truly awful sequel to that movie did. Plus, Lisa Kudrow (who plays the wife of Crystal's character) isn't in nearly enough movies — so anytime she gets to be in something halfway decent, that's a win for everybody.

21. America's Sweethearts (2001)

In 2001, it was considered an embarrassment of riches to have Julia Roberts, John Cusack, Catherine Zeta-Jones, and Billy Crystal as the four leads of a single film — not to mention an ensemble rounded out by Stanley Tucci, Alan Arkin, Christopher Walken, Hank Azaria, and Seth Green. But that's exactly what "America's Sweethearts" brought to the table, with Crystal also serving as producer and co-writer. 

Crystal plays publicist Lee Phillips, who decides that the best way to promote an upcoming movie starring Hollywood's hottest husband-and-wife acting partners Eddie Thomas and Gwen Harrison (Cusack and Zeta-Jones) is to have them pretend that they aren't actually going through a nasty divorce in real life. At the same time, Eddie is starting to fall for Gwen's sister (Roberts), while Gwen is also pursuing her own separate relationship — all of which Lee is trying to keep under wraps just long enough for the movie to come out. It's all a pretty entertaining look at celebrity culture and the way actors are "sold" to us, even if it doesn't quite have the bite that it could've to really make it exceptional.

20. Animalympics (1980)

When one thinks of Billy Crystal and animation, a certain round, green monster with one big eye probably comes to mind first. But Crystal has lent his distinctive pipes to a few other animated projects over the years, starting with this spoof that was specifically commissioned to run alongside NBC's coverage of the 1980 Olympic Games. Crystal voices four separate characters in "Animalympics" — reporter Rugs Turkell and athletes Joey Gongolong, Art Antica, and Bruce Kwakimoto, all spoofing then-current broadcasters and Olympic participants.

Joining Crystal were Gilda Radner, Harry Shearer (seven years before "The Simpsons"), and Michael Fremer, who each voiced multiple characters as well. For an "official" spoof, "Animalympics" is surprisingly funny and well-made, and it would've been great to have it as an ongoing franchise that returned with each subsequent Olympics. As it stands, it was a one-off special that has sadly been rarely seen since, showcasing Crystal's formidable voice acting talents many years before Pixar gave him a call.

19. Fathers' Day (1997)

Though Billy Crystal and Robin Williams have technically been in three films together, "Deconstructing Harry" and "Hamlet" are both large ensemble pieces and the two don't share any screen time in either one. Which makes their dual-headlining role in the comedy "Fathers' Day" their only true co-performance in a feature film — somewhat surprising given that the two were very close friends as well as longtime collaborators on HBO's "Comic Relief" charity comedy specials.

As it sometimes goes with this type of thing, "Fathers' Day" is far from being the comedy masterpiece that the long-awaited Billy Crystal/Robin Williams buddy comedy should've been. In fact, taking its script and giving it to almost any two other actors would've really hammered home just how mediocre it is. But there is no denying what a joy Crystal and Williams are together and how palpable their love and respect for each other are on-screen. Come to watch these two masters having the time of their lives working and ad-libbing together — just keep your expectations in check for everything going on around them at any given time.  

18. Small Apartments (2012)

Right off the bat, it needs to be made clear that "Small Apartments" is a vehicle for British comedy actor Matt Lucas. More to the point, it's a vehicle for how well Lucas plays completely bizarre characters. In fact, most of the performances in the movie are of the over-the-top, "playing to the cheap seats" variety, full of actors who seemingly joined the movie specifically to chew as much scenery as they can possibly stomach — and then chew some more.

While Billy Crystal would normally be right at home in such an environment, he actually gives one of the movie's more subdued performances. Critic John DeFore of the Hollywood Reporter says that Crystal's performance "roots the picture" and that it "[reminds] us how engaging the actor can be." As for the rest of the movie, your enjoyment of its very dark, very quirky brand of black comedy relies entirely on your tolerance for not only Lucas but also actors like Rebel Wilson, Juno Temple, and, yes, Johnny Knoxville, being told they can go all in and not hold back. 

17. Howl's Moving Castle (2004)

For years, even the most prominent anime got subpar dubbing, a trend that Studio Ghibli was determined to break. So they partnered with Disney in the late '90s to ensure that their films got top-of-the-line dialogue translations, in addition to Disney throwing their clout around to ensure that the English dubs of Studio Ghibli movies were full of A-list actors. In the case of 2004's "Howl's Moving Castle," this meant hiring the likes of Christian Bale, Emily Mortimer, Blythe Danner, Lauren Bacall, and Billy Crystal to lend their voices to the English dub.

In the movie, Crystal plays the part of Calcifer, a fire demon whose main form is just a face on a flickering flame on a log. But it's a Hayao Miyazaki movie, so there is much more to Calcifer than meets the eye, and he's imbued with more personality than many other animated movies' entire casts. Crystal brings his own charm and energy to Calcifer and makes the character his own, helping to make the English dub of "Howl's Moving Castle" a standout in the Studio Ghibli filmography. 

16. Untogether (2018)

Comedic actors often shift gears to dramatic roles in indie-style movies as they get older, and Billy Crystal is no exception to this. After being on cruise control for many of his 21st-century film performances, Crystal seems to have made a concerted effort in the last few years to pick (if not write) better roles for himself. One such example is his role in the 2019 indie drama "Untogether."

Written and directed by first-time filmmaker Emma Forrest, who had previously been a journalist and novelist, "Untogether" is, fittingly, about a writer (played by Jemima Kirke of "Girls"). Billy Crystal plays a rabbi with a history that goes back to his work in the Civil Rights movement, and critic Glenn Kenny says of his performance, "he's perfect." The movie itself got an admittedly tepid reception from critics as a whole, but "Untogether" is still worth checking out, if for no other reason than to show that, even into his 70s, Crystal remains at the top of his acting game. 

15. Forget Paris (1995)

Billy Crystal has only directed four movies so far, and appeared in three of them (he resisted the urge to give himself so much as a cameo in the HBO baseball biopic "61*"). Directing is something he clearly only does when just the right project comes his way, or it's a movie he wrote himself, and he wants to be the one to see it through. The latter is the case with the rom-com "Forget Paris," which Crystal not only directed but co-wrote and co-produced.

Considering that it was one of the all-time great rom-coms — yes, you know the one — that finally made Crystal a bona fide leading man movie star, it's commendable that he showed a certain amount of restraint in how few of them he appeared in throughout his career. But when he makes a rom-com, he makes it count, and "Forget Paris" is an extremely charming movie. There were few better female leads for this type of movie than Debra Winger, and "Forget Paris" also has a rare live-action Julie Kavner performance, of which there aren't nearly enough. 

14. Here Today (2021)

The last movie Billy Crystal had written prior to "Here Today" was "America's Sweethearts," making for a 21-year gap between film screenplays. It started to seem like his movie writing days were over and he was going to focus his pen on television and live productions for the remainder of his career — which would've been perfectly fine, of course. But "Here Today" serves as a perfect reminder of how much his writing was missed on the big screen, too.

Crystal plays an aging screenwriter who has had a celebrated career but is now struggling with dementia. He befriends a young woman (an excellent Tiffany Haddish) through rather humorous circumstances, and she helps him come to terms with his illness and reconnect with his family — who in turn take her in as one of their own. It's not the first time that Crystal examined the fleeting nature of fame and the way the world often turns its back on people once they pass their prime — more on that in the next entry. But his several decades of experience in the industry informing his writing, directing, and acting in "Here Today" definitely come across in the way he handles things with a warm, poignant touch.

13. Mr. Saturday Night (1992)

Billy Crystal was already pushing 40 when he finally became a legitimate movie star, and he certainly had to be aware that Hollywood isn't always kind to aging actors. We know now that his film career was only just getting started going into the '90s and he'd remain relevant for decades beyond that, but there was no way to be certain of that at the time. And that fear, that his peak was already happening and he'd soon be facing the downhill slope on the other side of it, informed not only his performance in "Mr. Saturday Night," but also his directing and co-writing of its script.

Crystal plays one of his few true jerk roles in his portrayal of Buddy Young Jr., though it's to his credit that you still find yourself feeling bad for him even as you watch him being terrible to everyone he interacts with. Crystal obviously rode his stand-up comedy success into a successful acting career, but it's not hard to see "Mr. Saturday Night" as his imagining of an alternate universe where that never happened. It's the kind of glum "what if?" story you can only tell about your past after you are secure in the knowledge that it didn't actually come to pass. 

12. Throw Momma from the Train (1987)

Based on the Alfred Hitchcock thriller, "Strangers on the Train," "Throw Momma from the Train" takes on a more comedic (although still darkly so) approach, with the trademark humor of its stars, Billy Crystal and Danny DeVito. Directed by DeVito himself in his big-screen directorial debut (aside from a couple of TV movies, anyway), the movie also stars the wonderful Anne Ramsey in one of the last films released before her death.

Needless to say, "Throw Momma" is a black comedy, and black comedies can be tough to pull off. But Crystal and DeVito are an incredibly effective on-screen duo, and they really shine in what would've otherwise been a tough-to-sell premise. But the lion's share of the credit for making the movie a classic goes to Ramsey, who was one of the best villains of the '80s and played a character you loved to hate as well as anyone ever has. 

11. Running Scared (1986)

It's basically a requirement that every comedic actor star in at least one buddy cop comedy during their career, and Billy Crystal got his out of the way early with "Running Scared." Paired with the should've-been-a-much-bigger-movie-star Gregory Hines, the pair play cops who attempt an early retirement in Florida — and, naturally, find themselves sucked into the "one last job" trope shortly after.

This will be the 500th time this list praises Crystal's chemistry with another actor, but the fact of the matter is that he's just great at playing off just about anyone — and his chemistry with Hines is no exception. What "Running Scared" also offers is a less violent, less mean-spirited — and a lot less racist — counterpart to "48 Hrs." And there is something to be said for that. As far as where "Running Scared" stands amidst the golden age of buddy comedies that featured "48 Hrs.," "Beverly Hills Cop," and "Lethal Weapon," it's probably inferior to all of those. But it's also the most underrated one of the bunch, and deserves to at least be in the conversation with them.

10. Analyze This (1999)

In the entry for "Analyze That," we point out that "Analyze This" is built around a very specific premise, one that it's a little too thin to warrant being turned into a franchise. But for just a single movie, it works fine and remains Robert De Niro's one of best comedic performances, equaled only by his work as Ben Stiller's father-in-law in "Meet the Parents." What "Analyze This" has over "Meet The Parents," however, is that it lets De Niro poke fun at his own tough-guy persona, whereas in the latter he's largely playing it straight against a comedy backdrop. It's one of the first times we really see De Niro have a sense of humor about himself, and it's extremely refreshing.

In fact, De Niro frequently manages to do something during "Analyze This" that few actors are capable of: steal scenes from Billy Crystal. And it's to Crystal's credit that he is perfectly fine with it, at times almost even seeming to play the straight man to De Niro's comedic performance rather than the other way around. 

9. Monsters University (2013)

Pixar has a few sequels under its belt by now, something they resisted earlier in the studio's tenure. But it wasn't until "Monsters University" that they did a full-on prequel, and it was definitely the smarter choice to further develop the "Monsters, Inc" universe. To follow Sully and Mike as they continue their careers in making kids laugh wouldn't have been the most compelling of premises for a movie, but flashing back to their college days together and seeing how they became friends is a delight.

Billy Crystal was made for cartoon voiceover work and it's somewhat surprising he hasn't done more of it — but the upside is that it makes his performance as Mike Wazowski that much more special. Well into his 60s at the time, Crystal voices a college-aged monster with as much energy and jubilance as a much younger actor would have. "Monsters University" also feels like more of a Mike Wazowski movie than the original did, which means there's more Billy Crystal as Mike — and nobody is complaining about that. 

8. This Is Spinal Tap (1984)

Billy Crystal's role in "This Is Spinal Tap" could definitely be classified as a cameo. But given that it was such an early role for him, and how iconic the movie itself has grown to become, it seems like a worthy inclusion to the list all the same. His performance as a mime waiter — in a scene with the equally pre-famous Dana Carvey — is brilliant, managing to be a standout in a film that is essentially just one iconic scene after another.

Beyond delivering the perfect "Mime is money" line, Crystal was able to showcase his formidable improvisational talents on the big screen for the first time. Even audiences who might not have known who he was were probably still left thinking, "Who is that guy, and when can I see him in more stuff?" Considering that one of Crystal's most famous "Saturday Night Live" roles was in his recurring "I hate when that happens" sketch with Christopher Guest — star and co-writer of "Spinal Tap" — it's surprising (and a little disappointing) that Crystal wasn't a fixture in Guest's movies going forward. 

7. Deconstructing Harry (1997)

With Woody Allen roping in pretty much every actor working in Hollywood from the late '70s through the '80s and '90s, it's extremely surprising that it took until 1997's "Deconstructing Harry" for Billy Crystal to finally appear in one of his films. But when Crystal finally did play a role in a Woody Allen movie, he made it count by literally playing the devil.

Well, to be clear, Crystal plays Larry, the best friend of Allen's titular character. It's just that the devil character from Harry's stories is based on his friend Larry, so that's why the devil looks like him. But it's the scene where Harry and Larry argue over which one of them is more evil that Crystal gets to show off, and it's a joy to watch. Well, it was, back when we could enjoy Woody Allen movies before everything we've since learned about him — but that shouldn't be held against Crystal nor his fantastic performance in "Deconstructing Harry." 

6. Standing Up, Falling Down (2019)

Even though Billy Crystal didn't have a hand in writing or directing "Standing Up, Falling Down," the fact of the matter is that it's his best movie in years and the most compelling example of why small indie dramedies are such a great fit for him at this stage in his career. The movie stars Ben Schwartz as a struggling stand-up comedian named Scott who is ready to abandon his dreams, but finds himself bonding with alcoholic dermatologist Marty (Crystal). Marty tries to use his failures as a cautionary tale for Scott, while Scott in turn helps Marty realize that he's not nearly the failure he paints himself to be.

It's a sweet little movie that has fantastic performances all around. Schwartz, currently best known as the voice of Sonic in the "Sonic the Hedgehog" film series, shows that he has a great side career in indie films alongside big-budget family comedies if he wants it. And Crystal continues to find a perfect balance at this stage in his career of playing age-appropriate characters, but ones that aren't just the typical "wise old man." If you check out any one under-the-radar Billy Crystal movie on this list, it should definitely be "Standing Up, Falling Down."

5. Hamlet (1996)

Hollywood tries its hand at adapting William Shakespeare's "Hamlet" every few years, and each one has its own unique gimmick or angle. For instance, the 2000 Ethan Hawke version reimagines the whole thing under the lens of Y2K, seeing Denmark as a tech company rather than a nation. What director Kenneth Branagh (who also plays the lead role of Hamlet himself) does with his 1996 version is offer the entire unabridged play on screen for the first time, resulting in a whopping four-hour epic.

Rotten Tomatoes critics claim that the movie "wastes none of its 242 minutes" — high praise indeed. "Hamlet" also doesn't waste the casting of any of its many supporting characters, including a delightful performance by Billy Crystal as one of the gravediggers. He delivers Shakespearean dialogue like a pro, and proves a more-than-worthy scene partner for the classically-trained Branagh. It's a quick scene, but a memorable one — and makes us wish Crystal would do more Shakespeare.

4. City Slickers (1991)

The standout performance in "City Slickers" is obviously that of Jack Palance, who earned an Academy Award for his performance. It's not often that a big studio comedy gets Oscars attention, especially for acting, which speaks to the quality of the movie overall. Billy Crystal is also at the top of his comedic game, backed by a talented (and stacked) cast that includes Daniel Stern, Bruno Kirby, David Paymer, Helen Slater, and many others — including the film debut of a young actor by the name of Jake Gyllenhaal as Crystal's son. 

"City Slickers" proves that not all studio comedies are lifeless and predictable, and does a lot with its premise to keep things interesting. It also handles middle-age ennui better than most movies, not going too far in trying to make the so-called "problems" of these 40-something white guys seem too much worse than they actually are. It pokes fun at them as much as it sympathizes with them, and that's why it all works. 

It really could've been the start of a fun action-comedy franchise, until "City Slickers II" completely ruined any chance of that happening. 

3. Monsters, Inc.

Billy Crystal has famously poked fun at himself for having turned down the role of Buzz Lightyear when it was offered to him. But he admits that Tim Allen was a better fit for the role anyway, and he would of course get another chance at Pixar immortality by way of Mike Wazowski in "Monsters, Inc." Not only is it a great showcase for his loose, ad-lib-heavy comedic style, but his chemistry (there it is again) with John Goodman as Sully led to one of the great animated buddy duos of the last twenty years.

After the somewhat mixed reception of "A Bug's Life," "Monsters, Inc." proved that Pixar was more than just "Toy Story" and helped to solidify the company's place as one of the best movie studios around — animated or otherwise. And much of that is due to the performances of Crystal, Goodman, and company in helping to bring the characters of this unique universe to life. 

2. When Harry Met Sally...

All due respect to "Annie Hall," but for our money, "When Harry Met Sally..." remains the best rom-com of all time. (It also helps that it doesn't have any of that baggage associated with the person who wrote, directed, and starred in the other one.) But "When Harry Met Sally..." succeeds where most romantic comedies fail in its honest depiction of adults who struggle with that line between platonic friendship and romantic love, and has its two leads develop a relationship in a gradual, realistic manner.

Any doubt as to whether Billy Crystal could carry a movie was gone after "When Harry Met Sally...," with his performance as Harry setting the template for the unconventional romantic leading man for years to come. Of course, he needs to share that credit with Meg Ryan, good in so many movies with Tom Hanks but never a better female counterpart in a rom-com relationship than she is here. Both Harry and Sally are bolstered by the wonderful performances of Bruno Kirby and Carrie Fisher — sadly both having since left us — as the token best friends whose relationship is an underrated highlight of the film.

1. The Princess Bride (1987)

It's hard to decide what the best Billy Crystal movie is. With him as the lead, "When Harry Met Sally..." is an obvious choice. But we also have to balance Crystal's presence in a movie with the quality of the film itself, and it's hard to argue that there is an overall better movie that Billy Crystal has ever been in than "The Princess Bride."

Crystal and his scene partner Carol Kane nearly steal the whole movie during their relatively short screen time as Miracle Max and his wife, Valerie. And that's saying a lot, considering that basically every scene in "The Princess Bride" has taken on a life of its own, with stalwart fans of almost every character. Many fantasy movies have a scene where one of the heroes has to visit some quirky elven character(s) in a forest village and enlist their magical assistance in continuing the journey. And the one in "The Princess Bride" might just be the best — and most definitely funniest — example of that trope in movie history.