Huey, Dewey, and Louie are the main characters of this story, all three of them voiced by Russi Taylor, who often voices them whenever they appear in contemporary Disney productions. When it's not her, it's Tony Anselmo, the modern voice of Donald Duck, who does them, and since I watched DuckTales a lot, I prefer Ms. Taylor's performance. Whenever Anselmo does them, he just does his Donald voice in a slightly higher pitch but Ms. Taylor is able to actually make them sound like young boys (and plus, I can understand them better when she does them anyway). In any case, their characterizations tend to differ from one cartoon to another: sometimes, they're characterized as just freaking mean little kids, which was the case in many of the classic cartoons, and other times, it's more like, "Boys will be boys." Their characterization here, as it often has since DuckTales, leans more to the latter: they're just very energetic and rambunctious kids who are excited about Christmas. They don't mean any harm by what they do but they also don't quite grasp what the holiday is really about and grow weary of it when they have to live through it day after day. However, they learn what it means when they decide to change things up one day by playing pranks on the family and end up unintentionally wrecking the house in the process. They're about to go sledding before Donald has a chance to get mad at them and that's when they see that, instead, of being angry, he's shattered by what's happened after the Christmas tree has fallen over onto him. They also finally bother to read the card that came with their sleds and discover that Donald and Daisy were trying hard to make this a special day for them full of love and family. Feeling guilty, they make the next day the best Christmas they can, having learned its true meaning and thereby breaking the time loop (very akin to Groundhog Day when Bill Murray stopped being a jerk and started being a good person).
Donald Duck, voiced, of course, by Tony Anselmo, is his usual hot-headed self here but, at the same time, he also wants this to be a great Christmas for everyone and especially for the boys to know how much he and the rest of the family care about them and what this time of year means to them. You wouldn't expect Donald to be this sentimental but, as I said in my review of Mickey's Christmas Carol, his mood tends to change from one appearance to another, as is the case with any character, I guess (ironically, in one of the segments in the sequel to this, his Christmas spirit is almost nonexistent). You've also got Daisy Duck (voiced by Tress MacNeille), Scrooge McDuck (voiced by Alan Young), and a character I'd never seen before this but may have been in the Donald Duck comics, Aunt Gertie (also voiced by Ms. MacNeille). Daisy and Scrooge are mainly just kind of there and don't do much significant: Daisy makes Christmas dinner, as well as tries to get Donald to kiss her under the mistletoe, and Scrooge often tries to get everyone to sing Christmas carols. However, there's a funny running joke with Aunt Gertie being one of those female relatives that kisses you to death whenever you see her and Huey, Dewey, and Louie end up soaking wet each time as a result. With each Christmas day, there's a new spin on it: they forget it's coming; they try to run from her but Donald forces them to let her kiss them; they put wetsuits on to avoid getting waterlogged; and finally kiss her themselves on the last day. Chip and Dale are also shown to be living in a birdhouse next to Donald's, playing with a toy train each time they're seen.
As is always the case in the modern era, Goofy is voiced by Bill Farmer, but since Dana Hill, the voice of Max on Goof Troop, had died from complications brought on by diabetes by this point, Shaun Fleming voices Max here. In Goof Troop, most of the comedy came from the fact that Max isn't as dim-witted or clumsy as his father and is actually a normal kid and that holds true here as well... for the most part. As usual, Goofy is a well-meaning father and an all-around good guy (he helps out a family that's been going through a rough patch lately) but he's dopey and clumsy, often causing his son a lot of embarrassment, but it's always clear that Max does love his father, even if he is an absolute idiot most of the time. As I said, Max is younger here than in Goof Troop (I'd say maybe seven or eight) and still believes Santa Claus is real, going to the trouble of having his Christmas list mailed to the North Pole. Unfortunately, mean old Pete (voiced by Jim Cummings) makes Max doubt Santa's existence and he starts trying to scientifically examine how Santa could possibly be real. Poor Goofy, who sincerely believes in Santa just like his son, does his best to explain away Max's fears but doesn't do a very good job at it. I do like this dynamic, as it feels like Max is approaching that age where most kids begin to doubt Santa's existence (it was a little later for me, though) and you also can't help but love Goofy for still having the innocence of a child even though he's an adult, no doubt due to his less than average intelligence.
Another interesting part of this story is how much Goofy and Max are actually alike. When Max uncovers his father playing Santa for the kids of that down on their luck family, he feels betrayed, that Goofy lied to him. Goofy tells Max that he was just trying to make those kids happy and also tries to convince Max that Santa is real since he's clearly lost his faith in it completely. Goofy puts sky-watch equipment on the roof and has Max stay up with him to keep a look out for him, but when there's a false alarm at one point, Max leaves Goofy on the roof and tries to go to bed. He can't sleep, though, and wishes that his father would just grow up... and that's when he sees something truly touching: Goofy shoveling the message, DON'T FORGET MAX, in the snow in his driveway. This makes Max realize how much his dad cares about him and that he's doing all of this for his sake. However, another false alarm, this time a burglar coming out of Pete's chimney that Goofy mistakes for Santa, ends up destroying Goofy's own faith in Santa. Now comes an interesting role reversal where Goofy is just like his son in that he's devastated that Santa apparently isn't real and Max tries to cheer his father up, doing the same stuff that he did earlier, even dressing up as Santa, which Goofy does fall for at first. The ruse doesn't last long but it brings them closer by the end, with Goofy saying that he may have let Max down but Max didn't let him down.
This is my personal favorite story in the film for many reasons. One, I love Mickey and Minnie Mouse to death. They're my favorite Disney characters. I know some may roll their eyes at that but I just can't help but find their relationship, in all its forms, to be very sweet and heartwarming, and I like seeing how much it's grown from their first appearances in the classic cartoons of the late 20's and 30's. It was mainly a love at first sight thing with them but it went on to become a slightly more complex one in some of the shorts in the 40's, which led to more sophisticated stories of their relationship like this one. Some may find it to be very saccharin (as with a lot of Disney's stuff in general) and that's fine, to each their own, but I've always really been drawn to these characters. Second, I really liked the way Wayne Allwine and Russi Taylor played Mickey and Minnie. If you didn't know, the two of them actually became a couple and married in real life. Not only did that make for an odd coincidence, to say the least, but as a result, the chemistry between Mickey and Minnie always felt very natural and strong because it was being done by a real couple (which is why I was quite hurt in 2009 when I heard that Allwine died). I feel that chemistry is particularly strong here. You can see the love these two have for each other, the lengths each of them are willing to go to in order to make the other happy, and the realization at the end of how much they truly mean to each other. It may not be the most realistic thing but I find it to be a nice, heartwarming bit of sentiment that's a breath of fresh air in a very cynical world.
While Pluto, Figaro, and Daisy Duck have small roles in this story, the other characters who are really notable are Mickey and Minnie's horrible employers. Mickey, unfortunately, works for Pete, who owns a Christmas tree lot and, as usual, he's a selfish, greedy jerk who tries to trick a poor family into buying an expensive tree they can't afford and, given what one of the kids says, probably couldn't even fit into their house by telling them that it's the last available one on the lot. Mickey, however, convinces the family to take a much smaller, cheaper tree and he makes a lot of money in tips, but Pete, furious at him for ruining his chance at selling one of the big trees, cruelly takes all of his money to make up for what he would have made and throws Mickey and Pluto off the lot. He ends up getting what's coming to him, though, when he unintentionally puts his lit cigar into his back-pocket and stupidly tries to put it out in paint, which ends up burning down his lot. He also ends up unintentionally spoiling Christmas for other people, as there's this Firehouse Toy Drive going on which Mickey and Pluto get roped into performing for because the band is too busy putting out the fire at the lot. Mickey, at first, isn't willing to perform since he needs to find a way to get Minnie's present before the day's over but, being the good guy he is, he goes through with it when he sees how much it means to the kids. That's what I like about Mickey Mouse: whether he's the rascal he once was or the overly nice character he's typically depicted as nowadays, he's always a good person at heart. (Incidentally, when he's dancing around on the stage, he does a dance move and makes a facial expression that's exactly like what he did in the 1940's short, Mickey's Birthday Party.)
Minnie's employer is actually a character from the past: Mortimer Mouse (voiced by Jeff Bennett). If you've seen the cartoon Mickey's Rival, you'll remember this guy as this obnoxious rat who was apparently an old boyfriend of Minnie's and made Mickey's life miserable for the short time he was around (I'm pretty sure this was his first appearance since that cartoon and he's been a recurring character in most Mickey Mouse-related stuff since then, trying to steal Minnie away from Mickey at every turn). Here, his characterization is a bit different, as he's portrayed as a pompous tycoon who's unable to remember Minnie's name and whose "Christmas bonus" for her turns out to be a big fruitcake. And after giving it to her, he tells her, "Now, scoot along back to the gift-wrapping department where you belong," with Bennett using that uppity, pompous voice he tends to use quite frequently all the while, which works very well for the character. Minnie's disappoint at this is quite heart-wrenching, especially when she wonders aloud how she's going to get Mickey's present now.
Going back to what I said in the introduction, in addition to the actual stories is a wraparound segment featuring three gifts underneath a Christmas tree signifying the stories' various themes and significances. Narrating the segment and introducing the stories in rhyme, Kelsey Grammer does a pretty good job of conveying the spirit of the season as well as the meaning of the stories, and to cap it all off, there's an ending segment where all of the main Disney characters come together to sing carols, finishing with, We Wish You a Merry Christmas, which I think is a nice, charming little way to wrap things up. As with most animated films, there were several directors involved, with Alex Mann directing Stuck On Christmas along with Bradley Raymond and some additional material as well as; Jun Falkenstein and Bill Speers directed A Very Goofy Christmas; and finally, Toby Shelton directed Mickey and Minnie's Gift of the Magi, as well as the interstitial segments. You'd think so many different directors would mean each segment would look different from the others but they actually all manage to gel together into a whole that's mostly consistent in style (something that Disney is quite good at), with only some slight differences here and there (for instance, Daisy looks a bit different in her small appearance in the Mickey and Minnie story from the way she did in Stuck On Christmas and Mickey and Minnie look different in their story than they do in the closing piece). One thing I think that the directors really got right is the wintery look of the stories, with those beautiful, pinkish sunsets that you often see this time of year and color schemes that make everything look and feel cold when it's outside and warm and cozy inside. I also thought the animation was quite fair for a direct to video film. Granted, it's definitely not theater-level, but it serves its purpose and does its job well. I know there are many who don't like the very neat and clean-looking animation look that's prominent since the 90's, maybe feeling that it looks a little too cold and sterile, but I myself usually prefer it to the more rough-looking stuff from around the same time (like on the TV show, Mickey's Mouse Works, where some shorts don't like quite as clean and polished as others).
Like everything else in this film, the music by J. Eric Schmidt may not be anything special but it does nothing less than serve its purpose well and exemplify the emotions of the scenes: Christmastime, happy, sad, funny, etc. Most of the music is just instrumental versions of classic Christmas songs and I particularly like the band version of Jingle Bells that plays during the scene where Mickey plays along with them for the toy-drive, as well as the Christmas carols sung by the characters at the end (those voice actors are all really good singers in their own right). Finally, I have to mention the version of Deck the Halls sung by the music group SheDaisy over the ending credits. Some may not like it when modern music groups like this do songs for Disney and other animated films but I think the way they sounded while performing this song was really nice and gives you that Christmas feeling.
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