Feel free to review our history and where we've finished by looking at this link:
http://www.hockey-reference.com/teams/MTL/
Actually, it looks like we did draft top five once due to standings. It was the very year the modern draft began in 1970. Ray Martyniuk was our pick as we missed the playoffs that year.
As far as I know though, 1970 would still be a weird draft year because you still had players who'd been signed to C-Forms (like Bobby Orr) as teenagers. So the draft took on more meaning in the next few years as the only way you could get those younger players was to draft them. The WHA made things more intersesting as well.
EDIT: Correction. Martyniuk was traded for as well from the California Seals.