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.

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.

"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. 

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. 

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. 

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.

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.

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. 

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. 

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.

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. 

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. 

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. 

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."

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. 

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.