The original LIFE AND LOVES OF A SHE-DEVIL is the most radical Ugly Duckling transformation I’ve seen.
Why would she be hugging Cardassians? Although, come to think of it… I could easily believe that, as a society, they’re really into S&M.
Strickly Ballroom has a well done one.
Dirty Dancing is supposed to be one but she has the same level of attractivenss for me through the entire movie.
Oh and My Fair Lady, of course.
Cher in Moonstruck goes from a tired-looking Italian widow with graying hair and a pretty dull wardrobe to. . .well, Cher. Tada!
Bette Davis and Cher (from the movies mentioned) both are women with strong features, who can look ugly or amazing depending on how you depict them.
It would be really hard to do such a transformation on Julia Roberts or Michelle Pfeiffer.
How about the opposite: beauty Charlize Theoron as truly plain-looking woman in “Monster”? Or the stunning Johnny Depp, his thick hair shaved into male pattern baldness, in the movie “Fear and loathing in Las Vegas”?
Or recently, Cameron Diaz as mousy woman in being John Malcovich.
Speaking of Star Trek, there’s 7 of 9’s transformation…
I’ll have to watch Moonstruck again. She was a widow?
IIRC she married her first husband for love and he died tragically, which fed into the whole bit with Olympia Dukakis telling her not to love the man she marries or marry the man she loves because it will only lead to misery. I seem to recall something about Loretta’s having “bad luck” with men as well but it’s been ages since I’ve seen it.
As for the reverse transformations, the examples given don’t apply since they are not transformations of the character within the course of the film from beautiful to ugly. An actual example would be Bette Davis in Mr. Skeffington who went from a beautiful young woman to an ugly old woman over the course of the story. Not to imply that old people are inherently ugly, but there are a lot of examples of attractive actors being aged through makeup with the result of being…not so attractive.
And one for the ladies: Jerry Lewis in The Nutty Professor.
Clark Kent into Superman
Which would be a terrific example of the “glasses equals ugly” trope that the OP specifically didn’t want.
Oh, and yet another Bette Davis example, involving the end of a film so despite its being 40 years old I’ll spoiler it:
In What Ever Happened to Baby Jane? Davis caked on her makeup every day, layering it new without washing off the old in imitation of what starlets in the earliest days of Hollywood supposedly did. She looks old, worn, lined and hideous. In the final sequence, when she’s dancing on the beach, there’s a near-complete transformation and she looks almost completely unwrinkled. Davis always claimed that it was completely from within. But there has been speculation that she had her makeup redone over the day’s lunch break, that she had a “mini-facelift” with tape to pull her skin taut or that the lighting was redone so as to burn the wrinkles out.
In Loaded Weapon 1, Allyce Beasley asks “Can I change before we go?” She leans forward to unravel her hairbun and when she leans back, she’s Kathy Ireland.
The film is also notable for being the only non-Trek film to feature William Shatner and James Doohan.
This was going to be my nomination.
(Apropos of nothing, Exit to Eden has been in heavy rotation on the crap movie channels lately. Did that movie kill Paul Mercurio’s career dead or what?)
I was talking more about how Christopher Reeve’s portrayal of Clark was so markedly different to his Superman, but even so, I knew it wasn’t really what was looked for.
Meh, too much effort. 
BTW, this reminded me of an old movie I saw in school about a man who made a deal with the devil where he couldn’t wash or groom himself for 7 years in order to get a girl (I think). If I remember, it was a pretty decent transformation. Anyone know the movie?
That sounds like a version of the folktale The Dirty Old Soldier. IIRC the story is from Russia. In the eighties a version was filmed as an episode of (title may be off) Fairy Tale Theatre. The soldier’s deal with the devil is actually that he gets a very large amount of money if he agrees not to wash, comb his hair, trim his nails, or even wipe his nose for seven years. He gets some money upfront and there are other conditions.
If the film you saw had an opening sequence featuring an animated minstrel changing clothing styles as he sung about his name in different countries (OTTOMH ‘In Germany, I’m Yohann. In Sweden, I am Yann. In Russia, I am Ivan. In America, I’m John!’) It was Fairy Tale Theatre.
Yeah it was, but they “cheated” by giving her a bad tooth gap before the potion. That’s not a makeover, that’s serious cosmetic dentistry.
I have a student with little, gapped teeth the like of which I’ve never seen before, and it’s got an effect, unfortunately.
Nope. Most of his credits after that, though, seem to be from Australia.