I’ve decided to start recording my real-life casting choices in my blog, because people are always asking me who I would cast as them, but when put on the spot, I can never remember past decisions. It really works the other way — rather than thinking up an actor to play one of my friends, I’ll be watching something and someone in the film or TV show will remind me of someone we know — a look, an outfit, something — and then I’ll be struck with casting nirvana. So really, I should capture these moments of enlightenment for future use.
So to begin:
If they ever make a movie of my friend Anthony’s life, they should cast Jack Black.
TurtleHead 
In looks only, of course. Anthony is just a titch more laid back than Jack Black. 🙂
I’ve told a bunch of my friends that you do this, and so if you ever meet them, you’ll probably get asked who you’d cast as them.
Who would you cast as Mr. Montreal?
The Jack Black casting is from King Kong — it’s a much more serious role for Jack and he tones it down enough that you see the Anthony in there :).
As for Mr. M…I find it hard to cast on-the-spot like that. I need to see someone famous first, then I’ll notice they look like someone I know — not the other way around. I’ll give it some thought but definitely anything I come up with right now will just horrify you :).