If you want a 455 the easiest route is a 307 donor for mounts and accessories. You'll be able to bolt it in and make it look like the factory did it without custom fab or hackery.
You have options for the transmission. If your main objective is 1/4 mile ETs then I'd probably use a TH400. Obviously it'd need a BOP bellhousing pattern to fit your 455.
If you plan to do much freeway driving you'll probably want to check into a Gearvendor overdrive. The other choice would be to have a 200-4r built. That won't be cheap because it'll need to be properly upgraded to handle the ridiculous torque that a 455 can dish out.
For simplicity's sake I'd recommend a 9" rearend. They're damn near indestructable and have the largest aftermarket support. You could also use an 8.5" but they're getting tough to find and would need some parts to live a long life of BBO 1/4 mile abuse. Chevy 12 bolt and Ford 8.8s have been swapped as well but are less common. Motorheadmike is a fan of the S60. Some site searching will get you specifics on each of them.
Don't overlook all the other stuff that goes with a major repowering like this...exhaust, fuel system upgrades, crossmembers, shifters, driveline, gauges, AC?, wiring, etc. That's all assuming that you're satisfied with your factory braking and suspension.
Not knowing you or your skill level, my advice would be to leave the car alone and enjoy it as-is until you've collected all the parts. It won't be a weekend project. If you're pretty handy and well equipped to do all of the work yourself I'm guessing you'll have at least 100 hours and (conservatively) $10k into it. If you're paying other people to do the work (correctly) then double your budget. An '80s Cutlass isn't immune to being an expensive hobby. Free cars are never free.
I'm not trying to scare you out of it -- in fact, I'd love to see you do it. We'd all just hate to see another driver fall into stalled project status. There's a lot of guys on this site with waaay more experience and knowledge than me and there's a million ways to build a Gbody. You'll learn a ton if you take a few days to wade through some build threads.
Hope that helps.