Back when I was in college I had a professor tell me that it was possible to make a simile between any two items you could think of. No matter what you picked, he said, there would be some connective tissue, even if it was a weak connection or an abstract idea. It's easy enough to see what a Juliet has in common with a rose, but if you work at it, you can figure out what a raven has in common with a desk. (They're both things that Poe wrote on, by the way.)
Watching the Artist, it seems like an odd fit for the other films that have been crowned Best Picture. It isn't a boldly envisioned epic, like Lawrence of Arabia or Gone with the Wind. It isn't a near perfect example of a moneymaking genre like Silence of the Lambs or Lord of the Rings: Return of the King. It isn't a film that's being used to retroactively reward a well regarded filmmaker's entire career like the Departed or A Beautiful Mind. It isn't something that announced itself as an instant classic like the Godfather or Casablanca.
But there are connections if you work at them. Like Driving Miss Daisy it's a period piece with a big part for a chauffeur. Like the Lost Weekend it's about a guy who is basically a drunk (although Lost Weekend takes this problem a bit more seriously.) Like All About Eve it's about the heartbreak and joy of being an actor. Like Crash it is a film that was lucky to come out in a year where there wasn't a really strong competitor that would have justifiably steamrolled past it.
It turns out, then, that if you want to put the Artist into perspective you just have to look at it next to the other films which have fallen by the wayside over the years. (And to be fair, also next to All About Eve, which is still a classic.) The film is well made enough that it's hard to dislike; it's got a genial spirit that's pleasant. But it also doesn't impress you much, nor does it linger after it's through. You can put it next to some of the best movies of all time and you would find things that they have in common, but I'm not sure why you'd want to.