Two F-150s and an F-250.
1971 Datsun 240z
early 2000’s Crown Vic
Some 50’s-60’s Alfa Romeo coupe
If I had the cash to buy three Ferraris, then I would buy one used economy car, and use the rest on something else.
And if I just had vouchers for the three cars, then I’d get three Ferraris (or whatever the most expensive car is I could find), sell them, and still use the money for something else. I’d get less for them used, but I could still get a lot of enjoyment out of that money.
But to play along as well as I can, if I could get three cars and I was assured that their resale value would magically depreciate to zero as soon as I took possession, then I’d go for a single-passenger all-electric with just enough cargo space for a load of groceries or a messenger bag, a plug-in hybrid with a lot of passenger space and room for a suitcase or so each, and a reliable pickup truck with at least a 4x8 bed. It’s a little early yet for any of them to be self-driving, but I’d at least look for models which are designed to be easily retrofitted for self-driving.
In the 60s, my dad collected cars. There are two from his collection, long gone now, that would be on my list:
1930 Packard 745 convertible coupe
The third car is also a convertible, wonderfully retro, with fins! Saw one parked on the street about 20 years ago and fell in love.
1948 Cadillac Model 62
But I’m afraid I will have to settle for getting more years out of my 2013 Chevy Volt.
One will definitely be a Lamborghini. Will be hard to nail down a model. Diablo, Countach, Aventador? Let’s go with the Aventador.
Then a truck for utility. Let’s say GMC Sierra Denali. Crew cab, of course.
American muscle. I’ll take a '70 Cutlass 442 convertible.
Given a week or so to really think about this, I might choose slightly differently. But off the cuff, these are my answers.
Yeah, I said 69, solely because I like the 3-spoke steering wheel offered only that year. But a 70 would work!
(Non-442s are actually quite available and reasonable.)
The most beautiful car ever, 1962 Corvette
Astin Martin DB11
Then probably a nice luxury SUV for when I just want to leisurely cruise around. Mercedes G-class
Only 3? Tough…
- Keep my 1985 Nissan 300ZX Turbo, but do a complete restore to showroom condition.
- A BMW i8 roadster
- A 1972 Olds Cutlass SS- the first car I ever owned, but this one I would completely trick out.
Save some money for some comfortable walking shoes, Dog. 
Give me a '63 Ferrari 330 LMB
Maybe a Gen 2 Camaro RS/SS or Z28. Make mine yellow. Add some nice modern stuff to make it strong and sound.
Third car would be something silly. Maybe a Schumacher championship winning Ferrari. Hey, it’s only money, right?
You’re going to get some hop-ons…
I want a 1965 Pontiac Bonneville with a 421 high output engine, a 4 barrel Carter carb, and all the fancy accessories.
I’d like a Packard with a twin six (i.e., a V-12) from the late 30s.
Something small for the third one, a nondescript-looking car that has a secret performance engine and excellent handling. Maybe a modified 1970 VW bug with a Porsche engine.
I’m in the fortunate position of being able to buy pretty much any car I want…but I don’t…which is probably why I could in the first place. Even if money was truly no object I’d struggle to pay a lot for a road car and probably just plump for something that gets the family comfortably to the continent summer and winter and isn’t ridiculously large for getting round our medieval market town. Perhaps a small-ish Audi SUV, maybe a SQ7. Ridiculously quick but practical. (but far. far more than I’d be willing to pay)
Mind you, when it comes to motorsport I’d spend my Musk-style billions on the following icons of motoring history, in ascending order of cost and attainability
A Lotus 49 - would have to be as driven by Jim Clark and in the green and gold livery - It would cost several million but it could be possible to get one.
Mclaren-Honda MP4/4 - 1988 vintage with Senna’s sweat still on the seat. - That would go for north of 20 million I suspect, Mclaren are unlikely to sell though.
And the ultimate (and one that I mentioned in a recent thread) The 722 300SLR that Moss drove to the 1955 Mille Miglia win. - It would easily be the most expensive car ever sold if Mercedes could be persuaded, but they can’t.
- BMW M5 2018 (deep red or metallic blue)
- BMW 740e 2018 (silver/grey)
- BMW M-Series ______ track car w/all the mods (red)* Gatopescado will advise on year and mods.
*A car trailer to tow with my current X3 will be needed, but I’ll spring for it myself.
However: if allowed, I would give up the 740 in exchange for total, authentic restoration of my '02 530i.
Color is important 'cuz current Bimmers are black and I need to diversify.
Ken Block’s Hoonicorn
1987 Chevy Malibu 2-door with some sort of Pro-street set up
Ford Focus RS
Oh, this is really tough but the three at the moment would be:
1)Ferrari 275 GTB Berlinetta, in blue because anyone can drive a red one… I’ve been in lust with this car ever since I first saw one on Chasing Classic Cars. The lines are just, right on this car and it’s a 2+2 so it’s practical. 
2) 1956 Mercedes 300C - My grandfather had one and I loved sitting in it when I was a kid.
3) 1988 Grand Wagoneer- Gotta haul the toys around somehow. I’d get it done up with custom running gear and modern amenities, though.
The first 2 would be cars I owned in my youth.
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1962 Pontiac Catalina convertible. Mine looked just like the one in the video except it had a red interior. It also had the tri-power setup and 8 lug wheels. Paid $50 for it. Got rid of it because it had electrical issues.
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1963 Mercury Comet convertible. Mine was dark blue with a white top and interior. 260 V8 and a 4 speed transmission. Drove it most of my junior year in high school. The only issue I had was the syncro on 2nd gear was shot, I had to shift 1st to 3rd when driving it. Spun a $2 oil pump shaft and burned up the engine.
My 3rd car would be a car I bought for $800 and built an oval track racer out of it.
3. 1966 Dodge Charger Hemi. It had been sitting for years when I got it. Pulled the Hemi and sold it for what I paid for the car. Dropped a 440 in it and drove it in a hobby car class at my local short track. Destroyed the car half way through the season. Actually came out ahead on that car, besides selling the engine I also sold the interior and a lot of the body trim and the grill.
[URL=“1962 Pontiac Catalina Convertible - YouTube”]
I’m not a car person. I’ve been driving 2 door Jeep Wranglers for decades and am happy with them.
[ol]
[li]Jeep Wrangler, manual transmission 2 door.[/li][li]MG Midget (I owned one when I was 23)[/li][li]VW Beetle (my first car)[/li][/ol]
Some of you folk have truly excellent taste. I’d particularly like to compliment the folk who nominated the 1998 era 911, the Jaguar E type, the Jaguar F type, and all of Chefguy’s picks. Some cars are works of art, and those especially just send a frisson up my spine.
For myself, I’d go with:
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The much lusted after car of my misspent youth, the 993 widebody Porsche 911. Twin turbo, of course, and in triple black.
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My “practical car” will be a Lotus Evora or an Aston Martin DB11. With suitably tasteful and subdued (as in, Stage 1 or 2 instead of Stage 3) performance mods. Color will be Laser Blue Metallic.
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And the remainder of my unlimited budget will be spent on a fully ground-up custom car like one of these. I’m afraid the work on that one will just never quite be done, and it will require many redesigns, drivetrain replacements, ground-up rebuilds, and enhancements over the rest of my life.
