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The Intern (2000)
I love it. No really, I do.
Yes, the sound production is awful. Yes, quite a bit of the acting is sub-par. Yes, the story leaves much to be desired. Yes, this is one of my favorite comedies of all time.
If you watch this movie, be prepared to strain to understand all the lines of dialogue and wince at the tinny, no low-end soundtrack. Someone should have been fired before this movie was completed for their apparent ineptitude at sound editing. I actually hated this movie upon first viewing, being unable to even finish it. It was only after I overheard a friend of mine laughing hysterically at it from the other room that I decided to give it a second chance.
It's a great idea to get a bunch of the fashion world to do cameos in a film like this; unfortunately they aren't known for the acting, and for good reason. Joan Rivers is just as hard to swallow as she is in real life, so be prepared. Dominique Swain over-acts, as per usual, but she is still likable.
The opening musical number is perfect in one respect: it sets you up for the unexpected. There is absolutely no reason for it, but it's funny. Is this an office comedy? A gay comedy? A romantic comedy? Is it, as another user posted, a whodunit? Yes, in all respects. The plot really can't decide which to be. It's very ambiguous.
Taking all of this into account, I still highly recommend this movie. If you go into it expecting it to be awful, you just might find a new favorite.