I have some ideas, I'll put them in alphabetical order, so I won't confuse myself
Adams Brothers Probe 16 (or replica) - It's an era on four wheels. It's lower than a current F1 car.
Alfa Romeo
8c spider - a bizarre Alfa-Ferrari, which people love to do coachwork around, so if I'm lazy I'll drop it off for a few months in Turin.
tipo 33 - the classic Le Mans look. Perfect curves. Probably pretty atrocious to drive off the track. I might still do the Mille Miglia in it
SZ - delicious Zagato weirdness
AMG 6x6 - yeah, nothing compares
Alpina Z8 - similar to the above in nature - laid back performance with great styling.
Alpine A110 - The Alpine to have.
BMW M1 - mid-engined 80s magic
CS prototype - the hyper saloon that never was
Brabus Biturbo - melding two I3 turbos into a V6 and stuffing it in the back of a Smart Roadster? That's the kind of insanity I love.
Bugatti EB110 - the low volume pre-Veyron. The Veyron is probably the better car, but this makes the EB110 all the more interesting
Type 57S Atalante (or maybe something like the Gangloff Drop Head Coupe) - arguably the best of the 30s
Citroen C6 - never has a luxury car looked this smooth. My father owned one, and I miss it.
Chevrolet El Camino - the only American car on this list, but the most American of all cars.
Ferrari
250 LM, to park beside the tipo 33
FF - for the shooting brake and the V12
Jaguar XJS12 - An 80s interpretation of the E-Type? Its looks are oddly satisfying
Lada Niva - I'd probably get a bunch of them, and do stupid things with them.
Lagonda - to park beside the later hyper-saloons.
Lamorghini's Estoque prototype - so wrong, yet so right. Parked next to the CS.
Lancia Stratos - Ferrari V6, awesome looks, irreplacable.
Lexus LFA - Overpriced, overengineered, fabulous.
Lotus
Esprit HC turbo - more mid-engined 80s magic, but so different from the M1.
Elite II - shooting brake! wheee
Maserati
222E - very nice lux coupé with some of the nicest 80s design
Quattroporte V - another design classic...and the Maserati V8 sound...
Bora - Citroen and Maserati team up? What can possibly go wrong?!
McMerc SLR - The only McLaren or Mercedes I'd have. That supercharger sound. I'd have two - one Sterling Moss, and one standard coupe.
Nissan Juke GTR - would have this over the Quashquai.
Panther 6 - Idspired by the Tyrell P34! Completely pointless and opulent! ...okay, so that's another American car.
Peugeot 406 coupé - some of the cleanest lines in car history. Great work by Bertone, not at all diminished by mass production.
405 T16 - The French police used these in their police force. Pedigree enough for me
Porsche GT1 Straßenversion - Porsche's first supercar was actually just built to race. Many wants.
Renault Clio V6 - functional side-scoops on a hatchback.
TwinRun concept next to it.
R5 Turbo on the other side.
Mégane II RS - mostly for the design.
Toyota Aygo crazy prototype - something to compare the TwinRun against
Vauxhall (Holden?) VXR8 Bathurst - the hooniest of all hoonmobiles.
VW XL - the first time VW has built something that truly went upmarket.
That's probably a decent starting collection. I wouldn't want to get carried away. Wouldn't drive any of those very much, but some are probably good for the occasional drive around the country side or classic rally event.
As a daily, I'd get an "old" Maybach 63 and a chauffeur. And an airplane that fits the car. Maybe a custom C130 with a silenced passenger cell, or something like that.
If I want to be more inconspicuous, I'd have a black Alfa Romeo 159 or Brera. Classy, but understated. And maybe a Polestar C30, in case I was expecting having to get out of a place quickly, but get in under the radar.