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    15 Classic Christmas Movies to Stream over the Holidays

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    Our list of classics is broad, from warm Old Hollywood favorites to the sort of boozy, vulgar entertainments that parents can watch after putting the kids to bed.Does a Christmas movie have to be about Christmas? If it merely takes place around Christmas, how prominently does the holiday have to feature for it to qualify? And really, must it be a merry Christmas? The Grinches and Scrooges of the world have streaming subscriptions, too.With a more elastic conception of the holiday in mind, we picked 15 Christmas movies of a broad variety, from warm Old Hollywood favorites to family-friendly modern comedies to the sort of boozy, vulgar entertainments that parents can watch after putting the kids to bed. (And yes, the oft-debated “Die Hard” did make the list. When is it ever a bad time to watch “Die Hard”?) These films are either on streaming services or available to rent on major platforms. Also, “Die Hard” returns to theaters Dec. 8.‘Christmas in Connecticut’ (1945)Stream it on Max. Rent it on Amazon, Apple TV, Google Play, Vudu and YouTube.Having established herself as a master of melodrama in “Stella Dallas,” a closet romantic in “The Lady Eve” and a duplicitous femme fatale in “Double Indemnity,” Barbara Stanwyck combines all three qualities into a winning performance in “Christmas in Connecticut,” a screwball holiday comedy with heart. Stanwyck plays a single New Yorker who’s been posing as a wife and mother from rural Connecticut to make her food column more appealing to American housewives. When asked to host Christmas dinner for a dashing war hero (Dennis Morgan), she scrambles desperately to sell her made-up persona, but amid the confusion over her fake husband and baby, she winds up falling for her guest.‘It’s a Wonderful Life’ (1946)Stream it on Amazon Prime Video. Rent it on Apple TV, Google Play, Vudu and YouTube.Released to mixed reviews and disappointing box office — particularly by the standards of the director Frank Capra, who was seen as a hitmaker after films like “It Happened One Night” and “Mr. Smith Goes to Washington” — “It’s a Wonderful Life” has become the undisputed star atop the holiday-movie tree. But what makes it so enduring ties into why it took a while to catch on: The joyful, tear-jerking ending is exceptionally hard-won, following a Christmas Eve that’s a dark night of the soul for George Bailey (James Stewart), a man whose despair nearly drives him to the brink. It’s only after meeting his guardian angel that George sees his value to his family and community.‘A Christmas Story’ (1983)Stream it on Max. Rent it on Amazon, Apple TV, Google Play, Vudu and YouTube.Jeff Gillen, left, and Peter Billingsley in “A Christmas Story.”Warner Bros.As if to compensate for making the holiday-themed slasher classic “Black Christmas” nine years earlier, the director Bob Clark turned to this nostalgia-soaked comedy, which has become a seasonal favorite, though it’s not without its horrors. The Parkers are the most disaster-prone family in their 1940s Midwestern town, and embarrassment is always around the corner for poor Ralphie (Peter Billingsley), who wants nothing more than a Red Ryder air rifle for Christmas, but is constantly told, “You’ll shoot your eye out.” In the lead-up to his big gift, Ralphie has an awful encounter with a mall Santa, decodes a disappointing secret message from Ovaltine and is forced to wear the pink bunny onesie his Aunt Clara got him. But Ralphie won’t be a put-upon kid forever.‘Gremlins’ (1984)Rent it on Amazon, Apple TV+, Google Play, Vudu and YouTube.An ideal double feature with “It’s a Wonderful Life,” Joe Dante’s mischievous comedy throws a Capraesque small town into chaos when an exotic Christmas present spawns the green marauders of the title. While in Chinatown on business, an eccentric inventor discovers a cute little animal called a mogwai and sneaks it back home to his family. But the new caretakers don’t follow important instructions, like keeping the mogwai away from water and not feeding it after midnight. It mutates into the innumerable creatures of the title, who take a juvenile delight in creating mayhem. Part monster movie, part live-action Looney Tunes, “Gremlins” leaves a trail of destruction through its snow-capped holiday idyll.‘Die Hard’ (1988)Stream it on Hulu. Rent it on Amazon, Apple TV, Google Play, Vudu and YouTube.Bruce Willis and Bonnie Bedelia in a scene from “Die Hard.”20th Century Fox, via Getty ImagesThere should be no argument over whether “Die Hard” is a true Christmas movie, given that John McClane (Bruce Willis) flies out to Los Angeles to spend the holiday with his estranged wife (Bonnie Bedelia), battles an armed band of European thieves who have taken over an office party and even dresses one unfortunate henchman in a Santa suit. Plus it’s a useful excuse to rewatch this impeccably crafted and influential action movie, which emphasizes McClane’s vulnerability as much as his resourcefulness and guile in outwitting a criminal mastermind (Alan Rickman) and perhaps saving his marriage in the process.‘The Muppet Christmas Carol’ (1992)Stream it on Disney+ and Hulu. Rent it on Amazon, Apple TV, Google Play, Vudu and YouTube.He may be surrounded by singing, dancing, mischief-making Muppets, but Michael Caine gives the role of Ebenezer Scrooge, the heartless miser of Charles Dickens’s “A Christmas Carol,” every bit the gravity of screen antecedents like Alastair Sim, Basil Rathbone and Albert Finney. This allows “The Muppet Christmas Carol” to position him as the ideal straight man, a grouchy counterpoint to the silliness of Kermit the Frog’s earnest Bob Cratchit, Miss Piggy as a typically brassy Emily Cratchit and the three offbeat ghosts who show Scrooge the path to redemption. The film proves it’s possible to honor Dickens while paying a visit to Fozzie Bear’s rubber chicken factory.‘Tim Burton’s the Nightmare Before Christmas’ (1993)Stream it on Disney+. Rent it on Amazon, Apple TV, Google Play, Vudu and YouTube.Jack Skellington (voiced by Chris Sarandon) in “Tim Burton’s the Nightmare Before Christmas.”Touchstone PicturesOn paper, “The Nightmare Before Christmas” sounds like a cynical proposition, an animated studio musical with a plot that covers both Halloween and Christmas, giving it a solid three-month window where it’s seasonally appropriate viewing. Yet Henry Selick’s stop-motion fantasy, made in collaboration with one of its producers, Tim Burton, has a dark, personal, idiosyncratic style that dispels any thought of commercial calculation. It has earned a legitimate cult following over the years. As the Pumpkin King of Skeleton Town, Jack Skellington (voiced by Chris Sarandon) inadvertently discovers the joys of Christmas Town and tries to bring the magic back home, with predictably demented and chaotic results.‘The Ref’ (1994)Rent it on Amazon, Google Play, Vudu and YouTube.The premise of this dark comedy sounds a little like the Humphrey Bogart noir “The Desperate Hours,” in which escaped felons hole up in a suburban home and take a family hostage. Only the twist of “The Ref” is that the crook, a cat burglar (Denis Leary) abandoned by his partner in the middle of a job, winds up captive himself to his hostages, a Connecticut couple (Kevin Spacey and Judy Davis) who cannot stop arguing. It becomes a Christmas Eve to survive when other members of the family turn up and the would-be felon takes on the role of reluctant counselor.‘Eyes Wide Shut’ (1999)Rent it on Amazon, Apple TV, Google Play, Vudu and YouTube.Tom Cruise and Nicole Kidman in “Eyes Wide Shut.”Warner BrothersThe marital odyssey in Stanley Kubrick’s dreamlike final film is book ended by Christmas backdrops that underline the state of a bourgeois marriage that threatens to collapse. After a fashionable party where his wife (Nicole Kidman) flirts shamelessly with a well-heeled Hungarian, a doctor (Tom Cruise) starts a fight with her about jealousy and temptation. From there, he embarks on a nocturnal adventure that leads to several frustrating encounters with other women, culminating in an exclusive sex party that he tries to attend without an invitation. Given the threat to this superficially stable and happy family, the holiday setting, rendered in warm lights and festive colors, stands out in sharp relief.‘Elf’ (2003)Stream it on Hulu and Max. Rent it on Amazon, Apple TV, Google Play, Vudu and YouTube.There was no more ideal choice to play an orphan raised by North Pole elves than Will Ferrell, whose ungainly, up-for-anything rambunctiousness had made him a breakout star on “Saturday Night Live.” “Elf” has the quality of an extended sketch, as Ferrell’s overgrown Buddy leaves Santa’s Workshop for New York City to find his real father (James Caan), an ornery children’s book publisher who works in the Empire State Building. His comic naïveté and relentless good cheer turn “Elf” into a fish-out-of-water comedy of disarming warmth, thanks largely to an ace supporting cast that includes Emily Deschanel, Ed Asner, Mary Steenburgen and Bob Newhart.‘Bad Santa’ (2003)Stream it on Paramount+. Rent it on Amazon, Apple TV, Google Play, Vudu and YouTube.For those who greet the holidays with dread — or simply like their eggnog extra-spiked — Terry Zwigoff’s dark comedy is the ultimate in Christmas counterprogramming, a relentlessly vulgar provocation that does have a heart if you squint hard enough to see it. Billy Bob Thornton stars as an alcoholic mall Santa who uses his access to rob department stores at the peak of the shopping season, provided he can stay sober long enough to crack the safe. His latest job is complicated by a sweet, outcast boy whose belief in Santa is unshakable, even when his hero is a grump with conspicuously foul breath.‘Kiss Kiss Bang Bang’ (2005)Rent it on Amazon, Apple TV, Google Play, Vudu and YouTube.Robert Downey Jr., left, and Val Kilmer in “Kiss Kiss Bang Bang.”Warner Bros.Since breaking into Hollywood with his script for “Lethal Weapon,” the writer Shane Black has set six of his films during Christmas in Los Angeles, where it’s too temperate to find obvious evidence of the season. His directing debut, the spiky neo-noir buddy-action comedy “Kiss Kiss Bang Bang,” loads up the soundtrack with a mix of traditional and irreverent Christmas songs. Its murder mystery starts at a fancy party where the most intriguing guest, an aspiring actress (Michelle Monaghan), appears in a deconstructed Santa outfit. Robert Downey Jr. plays a hilariously snarky thief who stumbles into an audition for a detective role, gets the part and then shadows a real-life private eye (Val Kilmer) on a case.‘A Christmas Tale’ (2008)Stream it on Mubi. Rent it on Amazon and Apple TV.The premise for this French ensemble piece sounds like a heartwarming holiday treacle: Playing the matriarch of a large family, the screen legend Catherine Deneuve gathers her three adult-age children and their significant others to announce that she has leukemia and needs a bone-marrow transplant. But the director, Arnaud Desplechin, who broke through with a three-hour film titled “My Sex Life (Or How I Got Into an Argument),” isn’t the sentimental type. “A Christmas Tale” exposes the many fault lines in this wildly dysfunctional family but it’s a disarmingly affectionate film, too, with a first-rate cast that includes Mathieu Amalric, Anne Consigny, Melvil Poupaud and Emmanuelle Devos.‘Carol’ (2015)Stream it on Netflix. Rent it on Amazon, Apple TV, Google Play, Vudu and YouTube.Rooney Mara and Cate Blanchett in “Carol.”Wilson Webb/The Weinstein CompanyDuring the Christmas rush at Frankenberg’s department store in 1952 Manhattan, a moment is shared by two women — one an aspiring young photographer (Rooney Mara) logging time as a clerk in a Santa hat, the other a wealthy married woman (Cate Blanchett) in a glamorous mink. What follows is a forbidden affair that bridges a chasm in age and class. The morality clause in the older woman’s marital contract threatens her financial security and her status as a mother. Yet “Carol” has a powerful romantic spirit all the same, buoyed by a wintry holiday backdrop that’s suggestive of a new home these women seek to find in each other.‘Le Pupille’ (2022)Stream it on Disney+.A deserving nominee for best live action short at the 2023 Oscars, Alice Rohrwacher’s charming and evocative 37-minute film takes place at an all-girls Catholic boarding school over Christmas during World War II. As the head nun keeps strict watch over these adorable, mischievous kids — they get their mouths soaped for grooving to a pop song on the radio — a young woman arrives with a scrumptious red custard cake, asking them to pray for her unfaithful boyfriend. The nun presents the kids with a cruel challenge: Can they prove their devotion to Jesus by resisting the temptation of this Christmas Day treat? More

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      Are ‘Elf’ and ‘Love Actually’ the Last Holiday Classics We’ll Ever Get?

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      The two comedies opened on the same date in 2003 and have stood the test of time. A changing Hollywood landscape might make another such day impossible.On Nov. 7, 2003, American audiences had the opportunity to see either “Elf” or “Love Actually” for the very first time in theaters. They could find themselves humming “Baby, It’s Cold Outside” along with Will Ferrell or sobbing to “Both Sides Now” with Emma Thompson. They could imagine themselves running through Central Park to save Santa or dashing through Heathrow to catch their beloved before a flight. And chances are, many of the moviegoers who watched those films on that fateful day in November have revisited them since. After all, both have become bona fide seasonal classics.Every year around this time, you’re likely to turn on the television and find one of them playing. “Love Actually,” the British multistory rom-com, has been debated to within an inch of its life. (Is it sweet? Cynical? Romantic? Fatphobic?) The broader Will Ferrell comedy “Elf” has been adapted into a Broadway musical and an animated TV special. You can even look up how to make Buddy the Elf’s spaghetti doused in M&Ms and chocolate syrup.“Elf” was an immediate hit, topping the box office during its second weekend and ultimately grossing about $220 million worldwide. “Love Actually,” which opened in limited release, had a slower burn but eventually grossed $244 million worldwide. Both now seem like relics of a different time — an era when movies received the kind of dedicated theatrical releases that allowed them to win over viewers and give them that hard-to-define classic status, putting them in a pantheon that includes the likes of “Miracle on 34th Street” and “Home Alone.” What are the chances that a new holiday film could join those ranks of those cherished comfort watches?These days it’s rare to find a movie like “Love Actually” or “Elf” in theaters. The holiday-themed titles that land on the big screen tend to be violent — aimed at audiences that can handle a little gore with their mistletoe. Last year, David Harbour played Santa as a John Wick-style killer in “Violent Night.” On Dec. 1, the bloody revenge tale “Silent Night” arrives from action filmmaker John Woo. It’s also billed as from “the producer of ‘John Wick.’” When did Christmas get so vengeful?The lighter fare, meanwhile, has migrated largely onto computer screens and televisions via streaming and cable. Some of the most insistent purveyors of material sweeter than eggnog are Hallmark, which spits out dozens of forgettable flicks every year, and Netflix, which has established what it calls a “Holiday Universe” that includes franchises like “The Princess Switch” with Vanessa Hudgens. Last year, one of its marquee titles was “Falling for Christmas,” featuring Lindsay Lohan in a snowy “Overboard” rip-off.Ferrell with Daniel Tay in “Elf,” which marries New York jokes with throwbacks to TV holiday specials.Alan Markfield/New Line ProductionsEven once bankable stars are putting their Christmas vehicles online. Amazon is set to release “Candy Cane Lane” in December. It stars Eddie Murphy in what was billed in a promotional email as his “first holiday film,” a distinction that seems to ignore “Trading Places.”On the one hand, thanks to the churn at places like Hallmark and Lifetime, which will collectively release upward of 50 new holiday movies this year, it feels as if the genre is more robust than ever. On the other, the idea of getting a new film that’s as revered and rewatched 20 years on as “Elf” and “Love Actually” feels far-fetched.For the somehow uninitiated: “Elf,” directed by Jon Favreau, charts the adventures of Ferrell’s jovial and naïve Buddy, a human who’s raised in the North Pole by Santa’s elves and who ventures to New York in search of his birth father, a cranky children’s book editor played by James Caan. The movie contains conscious throwbacks to Rankin/Bass animated Christmas specials, like “Rudolph the Red-Nosed Reindeer” (1964), as well as cheeky jokes about New York City without ever getting too racy. (My favorite bit is when Buddy says, “I traveled through the seven levels of the candy cane forest, passed the sea of swirly twirly gumdrops, and then I walked through the Lincoln Tunnel.”)Whereas “Elf” was rated PG, “Love Actually” drew an R; yet despite some nudity and cursing, it outdoes “Elf” in earnestness. The directorial debut of “Four Weddings and a Funeral” and “Notting Hill” scribe Richard Curtis, the movie weaves together the stories of lovestruck Londoners around the holidays. There’s Hugh Grant as the prime minister moony-eyed over one of his employees (Martine McCutcheon); Emma Thompson as the sad wife whose husband (Alan Rickman) is possibly straying; and Liam Neeson as the widower whose young stepson (Thomas Brodie-Sangster) has a big crush. The list goes on.When the two films were initially released, neither saw the other as competition, according to “Elf” producer Todd Komarnicki and “Love Actually” producer Tim Bevan of Working Title Films.“We were toe-to-toe battling with ‘Master and Commander,’” Komarnicki said, referring to the Peter Weir high-seas period drama starring Russell Crowe. He added, “For me, ‘Love Actually’ is just a movie that I really dug.” (Both holiday movies would land in the Top 20 highest grossing films worldwide for 2003, ahead of “Master and Commander.”)And Bevan didn’t even think of “Love Actually” as a Christmas movie. “You sort of knew that it was Christmas-y because of the songs and all the rest of it,” he said. “But it felt like a romantic comedy rather than a Christmas movie.”Instead, he viewed “Love Actually” as a follow-up to the successes of “Four Weddings and a Funeral” and “Notting Hill,” both of which contributed to the rise of the British rom-com as a bankable industry. To be clear, Bevan does understand why it’s so linked with Christmas.“It’s about eight or nine different strands where there are different great emotions going on about love and family and all of the rest of it,” he said. “That’s the element that makes it Christmas-y.”Christmas entertainment is, at this point, eternal, but looking back, the early 2000s were bursting with holiday spirit. After midcentury films like “It’s a Wonderful Life” and “Miracle on 34th Street” offered existential musings on the seasons, a wave of edgier new favorites emerged in the late ’80s and early ’90s. “National Lampoon’s Christmas Vacation” and “Home Alone,” both written by John Hughes, offered Yuletide satires of the nuclear family with zany antics. “Elf” and “Love Actually,” meanwhile, each felt, in their own way, like optimistic responses to the Sept. 11 attacks, with reminders that cynicism can be overcome. But 2003 also saw the release of “Bad Santa,” a pioneer in the now common subgenre of the raunchy Christmas movie that includes “The Night Before” (2015) and “A Bad Moms Christmas” (2017).It takes time, of course, for a movie to become a classic, which is why it’s easy to say definitively that “Elf” and “Love Actually” deserve that designation. “Probably a decade later you think, ‘Wow, people are still watching that movie at Christmas time,’” Bevan said of realizing “Love Actually” had become a perennial favorite.And while there are certainly external factors that go into the popularity of both of these titles — including the fact that television programmers throw them on ad nauseam in the winter months — there has to be some unconscious collective decision that a movie deserves to be watched time and time again. Partly it’s that these films were emblematic of a certain communal experience when audiences gathered to watch them way back in 2003. “The sad thing is, had we made both of those movies for streamers today, I would argue we would not be having this conversation in 20 years’ time,” Bevan said.While he and Kormanicki insisted their movies could get theatrical runs now, “Elf” and “Love Actually,” with their midbudget sensibilities, would probably feel like outliers in the current theatrical landscape. With a few exceptions — like 2019’s “Last Christmas,” based on the Wham! song — there doesn’t seem to be much of a home for holiday entertainment in theaters, unless it is somehow profane or bloody. Even Ferrell’s most recent attempt at Christmas fare, the 2022 Dickens-inspired musical “Spirited” with Ryan Reynolds, was made for Apple TV+, a streamer.Streaming was ostensibly supposed to make movies more accessible, but instead it just makes them feel more disposable. And that’s not to say the streamers haven’t released some genuinely engaging Christmas material among the heaps of dreck, like the visually inventive Netflix animated feature “Klaus” (2019) or Hulu’s queer rom-com, “Happiest Season” (2020), starring Kristen Stewart. Still, the holidays thrive on nostalgia, and it’s hard to be nostalgic for the latest Vanessa Hudgens princess movie you watched while simultaneously scrolling through your Instagram feed.If I’m being honest, in the past 20 years I’ve had “Elf” and “Love Actually” playing in the background countless times while I putter around or hang out with family, but that’s largely because I know them both nearly by heart. My mother typically demands a joint viewing of “Love Actually” at some point every year. And yet the reason I have such affection for it is because each subsequent viewing reminds me of a previous one, which in turn makes me think back to when I watched it for the first time in the basement of a multiplex in 2003. 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      Best James Caan Movies to Stream

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      Drama, comedy, suspense, action, kids’ movies — there was truly nothing he couldn’t do. Who else could star in both “The Godfather” and “Elf”?When James Caan’s family announced his death on Thursday, it sent shock waves through cinematic circles — not because his passing was particularly premature (he was 82), but because he seemed such a vibrant and outsize personality, you figured he just might live forever.He hadn’t retired, or even slowed down much, in old age. He co-starred (with Ellen Burstyn, Jane Curtin and Ann-Margret) in “Queen Bees” last year and has another film still due out. More than that, he had maintained an active presence on Twitter, frequently sharing images from his films and memories of his collaborators and always concluding his messages with the phrase “End of tweet.”Yet Caan was a series of contradictions: a Jewish actor best known for playing an Italian, a leading man who never quite became a movie star, an actor equally adept at playing strength and weakness, rage and vulnerability. His attack on his abusive brother-in-law in “The Godfather” is one of the most visceral scenes of violence in movie history. But just the year before, he had starred in a film still remembered for its ability to make men cry. We’ll begin our look at his long, varied career there.1971‘Brian’s Song’Rent or buy it on Amazon, Apple TV, Google Play, Vudu and YouTube.Caan had already banked several years of television work and a handful of juicy film roles (including memorable appearances in Howard Hawks’s “El Dorado” and “Red Line 7000” and Robert Altman’s “Countdown”) when he starred in this “ABC Movie of the Week.” Caan and Billy Dee Williams starred as the real-life Chicago Bears teammates Brian Piccolo and Gale Sayers, the first interracial roommates in the history of the N.F.L. and best friends until Piccolo’s untimely death from cancer in 1970. Caan and Williams’s easy rapport sells the relationship, and Caan is truly heartbreaking in the closing scenes, which prove a too-rare showcase for his tenderness and warmth.1972‘The Godfather’Stream it on Paramount+. Rent it on Amazon, Apple TV, Google Play, Vudu and YouTube.Caan’s breakthrough role came the following year in Francis Ford Coppola’s sensational adaptation of the best seller by Mario Puzo. The director — who had used Caan to great effect, in a much gentler role, in “The Rain People” (1969) — cast the actor as Sonny, the hot-tempered oldest brother in the Corleone clan. The studio wanted Caan to play Michael (executives didn’t care at all for this Pacino kid Coppola was stuck on), but the filmmaker knew Caan had the mixture of ladies’ man charisma and brute force so essential to Sonny. It was a scene-stealing role, and Caan took advantage of it, playing the character’s many memorable moments to the hilt: his memorable in flagrante delicto entrance, his mocking “bada bing!” moment with Michael, that street-fight humiliation of his brother-in-law and, most of all, his shocking, bullet-ridden last gasps on the Jones Beach Causeway.1974‘The Gambler’Rent or buy it onAmazon, Apple TV, Google Play, Vudu and YouTube.As with most of the actors associated with “The Godfather,” Caan was quickly elevated to leading roles in the wake of its astonishing success. The best of that bunch may well have been this spiky tale of a privileged English professor who finds that his high-society pedigree and formidable intellect are no match for a spiraling gambling addiction. Caan’s duality — his ability to seem to move between worlds, ethnicities and classes — was rarely more effective than here, as his Axel Freed must seem at home both in the classroom, lecturing about the works of Dostoyevsky, and in the back rooms of New York’s seedy gambling underbelly, trying to buy more time from his bookie.1975‘Rollerball’Rent or buy it on Amazon, Apple TV, and Vudu.In our current cinematic landscape, an actor who fronts critical successes like “The Godfather” and “The Gambler” is usually ripe for picking by the Superhero Industrial Complex, handed a nice payday and an easy shoot in exchange for lending class and gravitas to a popcorn movie. Caan’s taking the lead in Norman Jewison’s big-budget sports movie could have looked like the same move, downshifting his considerable onscreen intelligence into something a bit brawnier. But “Rollerball” is no typical sports movie. Set in the then-distant future of 2018, it’s a prescient warning of the dangers of corporate overreach, overt violence and class warfare in sports entertainment — and society in general — and Caan conveys both the character’s fierce physicality and his intellect with ease.1981‘Thief’Stream it on Tubi. Rent or buy it on Vudu.Caan turned in arguably his finest performance — and certainly his most soulful — in this astonishing combination of crime movie and middle-age melodrama from the writer-director Michael Mann (“Heat”). Mann specializes in working-class criminals, guys who see their work as a job and nothing more, a way to make a living without punching a clock. Few actors understood that character like Caan, who plays the safecracker, jewel thief and ex-con Frank as a man who will break the law but not his moral code, and who so longs for the fruits of his labor that he carries around a collage of his imagined perfect, suburban life like a mobile vision board. Caan wears the heaviness of the character like a winter coat; he does what he has to do to get by, forever grasping for the last big score that always seems just out of reach.1990‘Misery’Stream it on Showtime. Rent or buy it on most major platforms.Caan spent much of the ’80s in a self-imposed exile, burned out from his busy ’70s, battling addictions and caring for his children. He stepped back into the industry with this Rob Reiner adaptation of Stephen King’s best seller, but did so with a generosity of spirit: Rather than choosing a solo vehicle that would show off his gifts, he took the decidedly secondary role of bedridden novelist Paul Sheldon and ceded the spotlight to the relative newcomer Kathy Bates, who had the much showier role of his obsessed superfan Annie Wilkes. She won an Oscar, and thanked him profusely in her acceptance speech: “I really am your No. 1 fan, Jimmy.”1992‘Honeymoon in Vegas’Rent or buy it on Apple TV+; buy it on Amazon.Caan spent the ’90s easing into his new position as a respected character actor, with copious supporting roles both in film and on television. The remnants of Sonny Corleone made him a no-brainer for villain roles, and he played them well, but some of his most memorable work inverted and confounded those expectations. One of the best examples was this romantic comedy from the writer-director Andrew Bergman, starring Nicolas Cage as a newlywed who gambles away a weekend with his wife (Sarah Jessica Parker) to Caan’s high roller. On paper, the character is reprehensible — but Caan invests him with a lovelorn sweetness that lends the picture, and its central conflict, some unexpected ripples.1996‘Bottle Rocket’Stream it on HBO Max. Rent it on Amazon, Apple TV, Google Play, Vudu and YouTube.Caan may have had visions of John Travolta’s “Pulp Fiction” comeback when he accepted a supporting role in the up-and-coming Wes Anderson’s debut feature, a cockeyed caper picture about a crew of incompetent criminals. It didn’t have the same result — the film didn’t find its audience until years later, after Anderson had established himself — but Caan’s unsung comic side shines in the role of Mr. Henry, an imposing criminal mastermind (and the proprietor of a successful landscaping firm). It was one of his finest late-career performances, deploying his still-potent tough-guy demeanor and undercutting it with unexpected, self-aware wit.2003‘Elf’Stream it on HBO Max. Rent or buy on most major platforms.When you live and work for as long as Caan did, you become beloved by each generation for a different role, and if boomers loved him for “The Godfather” and Gen Xers for “Bottle Rocket,” this smash family comedy endeared him to Generation Z. A lesser actor, cast in the role of the father to the North Pole elf Buddy (Will Ferrell), might’ve winked or mugged and ruined the whole thing; Caan wisely played this harried dad close to the bone, keenly aware that the straighter his face, the funnier his scenes. Drama, comedy, suspense, action, kids’ movies — there was truly nothing James Caan couldn’t do. More