David Letterman and Jay Leno were late-night talk show rivals, but they have more in common than we realize. They both put their own spin on lat night TV. They are two of the richest comedians of all time, and both of them have impressive car collections. We already know a lot about Jay Leno’s car collection, but David Letterman’s car collection will make any car enthusiast drool. Let’s take a look at some of the vehicles in his fleet (including a surprising British beauty at No. 9).
16. 1960 Austin-Healey Bugeye Sprite
Estimated value: $33,800
If you expected a man worth roughly $400 million to spend his money only on multi-million dollar cars, then you thought wrong. The Bugeye, which gets its name from the large, round headlights that look like they’re popping out of the hood, might not be worth much, but we’re guessing the small and sporty two-door is really fun to drive.
Next: A homegrown classic.
15. 1973 Chevrolet C20 Cheyenne
Estimated value: $34,700
As we’ll find out later, David Letterman’s car collection contains a ton of European classics. But there’s room enough for this classic American pickup truck. The C20 has been redesigned several times since it debuted in 1959, but something about the 1973 version appeals to Letterman.
Next: A blast from the past.
14. 1959 MGA Twin Cam 1588CC
Estimated value: $57,000
The 1959 MG Twin Cam 1588 is a blast from the past. Not only is it a classic car from the English automaker, but it’s similar to the Austin-Healy Bugeye Sprite that started our list in that it’s a sporty car that’s fun to drive. It just goes to show that a car collection doesn’t have to include only supercars or limited-edition classics.
Next: David Letterman and Jerry Seinfeld are on the same page.
13. 1988 Porsche 911 Carrera Coupe
Estimated value: $84,700
Something about being a comedian must lend itself to being a Porsche fan. Jerry Seinfeld is a notable enthusiast, and David Letter has several in his collection, too. This might not be one of the most expensive Porsches ever sold, but it’s still one of the most beautiful rides in David Letterman’s car collection.
Next: A street-legal car with racetrack roots.
12. 1961 Austin-Healey 3000 MK1
Estimated value: $97,000
It might not look like much now, but in its day, the Austin-Healey 3000 MK1 was a world-class race car. But you don’t have to be a professional drive to enjoy this machine. Its 124 horsepower engine packs a punch, but the classic styling makes the two-seater a fun way to get around town.
Next: It looks great even when it’s parked.
11. 1988 Ferrari 328 GTS
Estimated value: $112,000
Do you want power? With an eight-cylinder engine producing 270 horsepower and a top speed of 163 mph, the 328 GTS delivers. The smooth lines make it look great even when it’s parked, and it’s an exclusive vehicle since less than 1,600 were made. This is just one of 10 Ferraris in David Letterman’s car collection.
Next: That was then, this is now.
10. 1956 Austin-Healy 100-4 BN2
Estimated value: $130,000
The 100-4 BN2 was designed to be fast but cheap when it first hit the streets in 1953. That was then, and this is now. What was a cheap car for speed demons is now a valuable collectible, and David Letterman has one of these two-door roadsters sitting in his garage.
Next: A surprising British beauty.
9. 1955 Jaguar XK 140
Estimated value: $137,000
David Letterman made a fortune on TV, and Netflix made him one of the highest-paid streaming stars with his limited-run interview show. He used some of that money to buy this surprising British beauty. Why is it surprising? Because it’s not an Aston Martin, Bentley, McLaren, or Rolls Royce, which are more high-end automakers. Jaguar’s XK 140 didn’t so much supplant the XK 120 as the flagship sports car as carry the torch for the next leg. Jaguar made less than 9,000 XK 140 cars between 1954 and 1957.
Next: A car with a special place in history.
8. 1964 Porsche 356C
Estimated value: $173,000
As we mentioned earlier, even though Jerry Seinfeld is a well-known Porsche nut, David Letterman is right there with him. He reportedly has eight of them in the garage, and this classic is one of them. The 956 C was the car that preceded the 911 in Porsche’s lineup and the last of the 956s, so it holds a special place in the carmaker’s history.
Next: A car without a roof is still worth a lot.
7. 1961 Porsche 356 Cabriolet
Estimated value: $275,000
David Letterman made millions from his late-night hosting duties, and Netflix paid him a king’s ransom for a limited-run interview show. Given his fortune and his obvious love of cars, it won’t be long before he owns one of the most insanely impressive car collections, if he doesn’t already. This Porsche convertible is one of the highlights.
Next: Let’s go low.
6. 1983 Ferrari 512 BBi
Estimated value: $300,000
This is another of the 10 Ferraris in David Letterman’s car collection, and even though it’s not the most valuable, it’s one of the most interesting. Since it doesn’t have an oil pan taking up space under the engine, it’s extremely low to the ground, even by Ferrari standards. Less than 2,000 of these were made in eight years, and none were officially exported to the U.S., according to Hagerty, but Letterman has one in his garage.
Next: This vehicle is track ready.
5. 1969 Ferrari Dino 246 GTS
Estimated value: $369,000
The first Dinos made by Ferrari were built for the race track. When the company started building street-legal versions in 1968, it retained the Dino name. The Dino 246 GTS in David Letterman’s car collection is likely the more rare version made with an aluminum body and engine block, as opposed to the steel and cast iron, respectively, of later mass-produced versions.
Next: You might not recognize this car in traffic.
4. 1963 Ferrari 250 GTE
Estimated value: $531,000
With its straight lines and larger cabin for four people, the 1963 Ferrari 250 GTE doesn’t look like a typical Ferrari, so you might not recognize it in traffic. It wasn’t appreciated at the time, but it’s considered a classic these days. Less than 1,000 of these rolled off the assembly line between 1959 and 1963, and its rarity makes a coveted collector’s item and one of Letterman’s prized cars.
Next: A limited edition from an iconic automaker.
3. 1956 Porsche 356 1500 GS Carrera
Estimated value: $855,000
Yes, it’s another Porsche 356 in David Letterman’s car collection, but this is the one that makes enthusiasts’ eyes go wide. Of all the versions of the 256 Porsche produced in the 1950s and 60s, the 1500 GS Carrera is one of the most coveted of all. A classic car from an iconic automaker produced in limited numbers, this vehicle is a sparkling gem in Letterman’s garage.
Next: This car is nearly one of a kind.
2. 1963 Ferrari 250 GT Lusso
Estimated value: $1.85 million
Don’t get confused — yes, we discussed a 1963 Ferrari 250 a minute ago, but this one is worth nearly four times as much as the ’63 250 GTE. Why? For one, the Lusso was the more luxurious version with more leather. The other reason it’s so valuable is that Ferrari produced only 350 between 1962 and 1964.
Next: The most valuable car Letterman owns.
1. 1985 Ferrari 288 GTO
Estimated value: $2.7 million
This Ferrari has everything a serious enthusiast could want: A beautiful look, serious power, and unrivaled exclusivity. The 288 GTO’s racing origins ensure it has a sleek look, which its sloped nose attests to. With twin turbochargers attached to a 2,855 CC engine, it reaches nearly 190 mph. And with just 272 produced, it’s incredibly exclusive. It’s one of the finest cars out there, and it’s a highlight in David Letterman’s car collection.
All vehicle values are estimates courtesy of Hagerty.