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20 Holiday Movies Starring Comedians

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There are a whole lot of holiday movies starring comedians, either because they provide a great way for comedians to break into movies (with built-in "family" audiences) or because holiday movies are so busy getting stuffed with good cheer and warm feelings that they fall short on comic relief. Whatever the reason, check out this list to see which comics have created lasting classics and which ones should find a new holiday.

1. Will Ferrell - 'Elf' (2003)

DVD cover art for 2003 holiday movie Elf
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Saturday Night Live star Will Ferrell proved he could carry a movie with 2003's Elf, perhaps the only holiday film of the new millennium to instantly achieve "new classic" status. Ferrell's character, Buddy the Elf, gives the comedian his most likable role to date and is a perfect showcase for his man-child approach to comedy. Though the movie softens too much in the third act -- giving up on the comedy in favor of some feel-good "family" stuff -- the first two-thirds are really enjoyable. Director Jon Favreau adds some nice touches (dig the stop-motion animation!), but it's really Ferrell's show here.
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2. Bill Murray - 'Scrooged' (1988)

DVD cover art for 1988 holiday comedy Scrooged
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If Elf gave Will Ferrell the perfect sweet-but-naive character vehicle, than 1988's Scrooged did the same for Bill Murray, only in the exact opposite direction. Consider it the anti-Elf. It would be hard to find an angrier, more black-hearted holiday comedy -- particularly one that's supposed to warm our hearts by the end. This re-telling of Charles Dickens' A Christmas Carol updates the material for 1980s corporate America, making Bill Murray the crankiest, darkest Scrooge to hit the screen (at one point, he suggests stapling antlers to mice). Working for a script by pitch-black SNL patron saint Michael O'Donoghue, this is a movie that seems to hate everyone. Murray -- who often seems to hate everyone himself -- is perfectly cast.
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3. Chevy Chase - 'National Lampoon's Christmas Vacation' (1989)

DVD cover art for 1989 holiday comedy National Lampoon's Christmas Vacation
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After the dismal European Vacation, Chevy Chase and the National Lampoon crew bounced back with 1989's Christmas Vaction -- the second funniest film in the Griswold family franchise. More a series of set pieces than a coherent story, Christmas Vacation keeps the Griswold family at home for the holidays, where they're forced to confront sledding accidents, visiting in-laws, squirrels and disappointing Christmas bonuses. As far as comedians go, Chevy Chase pretty much owns Christmas; this one is on a short list of holiday films that deserves to be watched every year.
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4. Tim Allen - 'The Santa Clause' (1994)

DVD cover art for 1994 holiday comedy The Santa Clause
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It may seem strange -- and a little sick -- that a holiday film be based around the premise that Santa Clause has died, but that's exactly the setup of the 1994 Disney film The Santa Clause. And, apparently, audiences didn't mind; the movie became a huge hit, spawned a successful franchise and made a (sort of) movie star out of comedian Tim Allen. He would return to the role -- a guy who accidentally kills Santa and has to take his place (it's a family film) -- twice more in The Santa Clause 2 (2002) and The Santa Clause 3: The Escape Clause (2000), the latter of which also starred comedian Martin Short as Jack Frost. Mostly kid stuff -- assuming kids don't mind finding out Santa has died and been replaced by the guy from Home Improvement.
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5. Jim Carrey - 'How the Grinch Stole Christmas' (2000)

DVD cover art for the 2000 holiday movie How the Grinch Stole Christmas
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Director Ron Howard and comedian Jim Carrey took it upon themselves to transform the much-loved Dr. Seuss book, How the Grinch Stole Christmas, into a live-action feature film. The results are a strange mix of broad humor (thanks to Carrey), gooey family stuff and a look that's the stuff of nightmares. Carrey is buried under impressive makeup (courtesy of Rick Baker), but it limits his ability to be expressive (a lesson the filmmakers should have learned from The Mask). That means he's got to find other ways of mugging, which he does primarily with a vocal affectation that sounds nothing like the way you might expect The Grinch to talk.
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6. Adam Sandler - 'Eight Crazy Nights'

DVD cover art for 2002 holiday comedy Adam Sandler's Eight Crazy Nights
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It's rare that a holiday film celebrate anything other than Christmas, so you've at least got to give the 2002 animated Adam Sandler film Eight Crazy Nights for recognizing that people do celebrate in other ways. Unfortunately, the depiction of Hanukkah is the only thing this movie's got going for it -- unless you consider ugly animation, a loathsome central character, would-be sentiment towards a diminutive and annoyingly-voiced (also by Sandler) referee named "Whitey" checks in the "plus" column. Written, produced by and starring Sandler (sort of), this is a film that gets its biggest laughs from the sight of animated reindeer pooping -- a joke it repeats more than once. You kind of know how the reindeer feel.

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7. Stan Laurel & Oliver Hardy - 'Babes in Toyland' (1934)

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This 1934 musical comedy starring legendary comedy duo Stan Laurel and Oliver Hardy isn't one of their best films, but is still well-loved and considered a holiday classic. The plot, loosely based on a 1903 operetta, is a little needlessly complicated, but the scope and ambition of the comedy are impressive -- particularly for the time period. Re-released in 1948 as March of the Wooden Soldiers, the movie exists in many alternate versions (including different edits and a computer colorized version), so be wary of which one you seek out -- especially because it's now in the public domain and can be put out by just about anyone.
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8. Denis Leary - 'The Ref' (1994)

DVD cover art for the 1994 comedy The Ref
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Acerbic comic Denis Leary stars in this under-appreciated 1994 comedy, directed by the late Ted Demme and co-starring a then fairly unknown Kevin Spacey. The movie is a perfect vehicle for Leary's comic persona in the 1990s; he's a misanthropic burglar who gets trapped on Christmas with a feuding family. This is a holiday movie for people who may not like traditional holiday movies, and unlike, say, Scrooged, it tempers its black comedy with some genuine emotion. It's not all just misery and hatred. Leary wouldn't find another role this well-suited for him until TV shows like The Job and Rescue Me.

9. Steve Martin - 'Mixed Nuts' (1994)

DVD cover art for 1994 holiday comedy Mixed Nuts
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This 1994 Steve Martin comedy is a mess, but notable because it features a whole mess of comedians including Robert Klein, Madeline Kahn, Adam Sandler, Garry Shandling and Jon Stewart. About a group of wacky characters working at a suicide-prevention hotline on Christmas Eve, it's obvious that writer/director Nora Ephron was going for the kind of dark comedy that something like The Ref achieved far more effortlessly. It's mostly unpleasant and unfunny, but you do have to appreciate that cast of comedians.

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10. Jack Black - 'The Holiday' (2006)

DVD cover art for 2006 holiday comedy The Holiday
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Comedian Jack Black is cast waaay against type in Nancy Meyers' 2006 romantic comedy The Holiday. Normally a shaggy, hard-rocking comedic anarchist, here Black is a less-shaggy, sensitive and lovable composer romantically paired with fish-out-of-water Kate Winslet over a Christmas holiday. The notion that he's the "guy least likely" is exactly why Black is cast, but he dials down his energy so much that he comes off like a noodle of a nice guy. Wouldn't it have been more interesting to see Winslet -- who carries most of their scenes together -- fall in love with the usual Jack Black? That's a movie worth seeing. The Holiday is pleasant enough (but criminally overlong) as a love letter to movies, but cuts the balls off its chief comic asset.
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