David Letterman Is Not Slowing Down

The talk-show superstar may have bid farewell to late-night TV, but he still has plenty of drive.

Dan Carney

Nov 23, 2015

When David Letterman slid out from behind his modernist, L-shaped desk for the final time on May 20, passing the keys to the Ed Sullivan Theater to Stephen Colbert, one might have expected him to take it easy. After 33 years as a television fixture, he’d earned a break.

But here he is, not two months later, pulling on a crimson fireproof racing suit, slipping a helmet over his head, and preparing to insert his lanky frame into the cockpit of a cantankerous 1963 Watson roadster in the breezy number-two garage at the Indianapolis Motor Speedway.

Instead of slowing down, today Letterman is speeding up.

Sleek and potent, with tall, spindly wheels, skinny tires, and an enormous steering wheel for leverage, the Watson is not just any vintage racecar. It’s the very machine Parnelli Jones piloted to victory in the Indianapolis 500 back in 1963, just a few miles from where Letterman—a racing fan since childhood grew up. A few decades later, Letterman’s fame and his role as a co-owner of the Rahal Letterman Lanigan Racing IndyCar team create opportunities like these.

“I’ve played softball with my show friends at Yankee Stadium, and this reminds me exactly of that,” he says.

The Watson, dating from an era when deaths at Indy were commonplace, doesn’t suffer fools gladly. Letterman confronts this reality as he settles behind the Watson’s huge steering wheel.

“Do you feel comfortable?” a support crew member asks.

“No, I don’t feel comfortable,” he deadpans. “I haven’t felt comfortable in several years.” I ask him how he slept last night. “Fitfully,” he says. “I slept fitfully. Honest to God, I was scared silly.”

Like the car, Letterman’s racing suit is a loaner. It belongs to Graham Rahal, the IndyCar driver—of whom Maxim and Steak ‘n Shake are proud sponsors—who finished the season ranked fourth. Letterman looks trim and healthy. The time off has been good for him. The team’s co-owner, Bobby Rahal, the 1986 Indy 500 winner and Graham’s father, saunters over. “I can’t wait to tell Graham how good you look in his suit,” he says.

Letterman examines the Watson. Though the ancient speedster looks a little obsolete to the modern eye, its 180-mph and 400-horsepower worth of methanol-fueled fury have the deadly efficiency of purpose of a North American P-51 Mustang warbird. Pointing to the car’s tires, he asks, “Those are the smaller era tires, right?” Come to think of it, he is right: The Watson is resting on replacement tires that are a touch smaller than the ones the car was originally designed to ride on. Turns out they don’t make that size anymore.

As Jerry Seinfeld might ask, What’s the deal with comedians and cars, anyway? After all, both he and Jay Leno are fanatical motorheads with enormous personal collections. As for Letterman, his own garage of classics is smaller and more personal. Letterman enjoys and appreciates cars, but he doesn’t obsess over them.

The former late-night host wants the passion to be passed on: He says he hopes his son, Harry, 11, learns to drive a manual transmission before long, and falls in love with Letterman’s geriatric Austin Healey Sprite and some of the other “British and Italian and American brightly painted junk” in his collection. “Some of these cars that I have now are 40 and 50 years old,” Letterman says. “When [Harry] gets old enough to drive, they will really, really be old. Hopefully, at the reading of the will, he’ll say, ‘Yes! I get that one!’”

Letterman’s daily ride is far simpler, due to the hassle of his once-regular commute. “I used to have to drive to work to a job in the city,” he notes drily. He relied on an old, comfortable Toyota Land Cruiser. Surely, Leno and Seinfeld would be aghast.

More interesting is his Volvo station wagon, a 1995 960 with a fearsome V-8 engine installed. The plaything was recommended by a fellow superstar and IndyCar team co-owner: the late Paul Newman. This was in 1995. Newman was ordering one of the cars for himself, Letterman says, and he called to ask if Letterman would like one, too.

“Sure, I’ll take one,” Letterman replied casually, as if buying a custom-built car sight unseen over the phone was a perfectly natural thing to do.

“You want a puffer on that?” queried Newman. A supercharger.

“Of course I want a puffer on that,” Letterman replied. Finally, the only question that remained was the car’s color: red or blue? Letterman picked red, a choice he regretted after seeing it. “Blue was the color to have that year,” he admits now. “The red is not flattering to the car.”

Newman called back on a Super Bowl Sunday to let Letterman know the car was ready. Would he like him to drive it over and take Letterman for a ride to show him what the hot-rod Volvo could do?

“That ride was worth the price of the car,” Letterman recalls.

He also has a new Tesla, though neither his wife, Regina, nor his son will ride in it with him. “I thought, as a family, we were saving the planet,” Letterman says, but apparently, the Tesla’s new-car smell offended them.

“Isn’t that why you buy a new car?” he thunders with indignity. “For the new-car smell?” Now the Tesla sits, plugged into its charger. “I’m done with trying to save the planet,” he grouses with feigned disgust.

Letterman has been an auto-racing fan since childhood—as are most Indianapolis natives. “I inherited it,” he says. “It was genetic. Every May, that’s what you did. It concluded the brutal central Indiana winters. The whole thing was symbolic.”

His decision to follow Newman’s lead and invest in an IndyCar team grew out of his search for guests to book on The Late Show. Having made his network debut in 1971 with a track-side interview he conducted with Mario Andretti for ABC Sports (the clip is on YouTube and well worth a look), Letterman had long enjoyed hanging out with drivers and began routinely scheduling them as guests.

“We used to have a lot of race people on the show,” he recalls. “I met Bobby in 1986, after he won the Indy 500, and he was tremendous. We would have him on from time to time after that, and we got to be good friends that way.”

Later, Rahal launched his own IndyCar team, eventually inviting Letterman to participate as a co-owner. Without that friendship and Rahal’s invitation, Letterman says he would never have sought out the ownership that put him in the pit lane when the team won the Indy 500 in 2004 with driver Buddy Rice.

“The birth of my son, my heart surgery, and winning the Indy 500,” he says. “Those are the three big ones for me.”

Now he can add driving at the Speedway to the list.

The Speedway staffers roll the Watson out into the pit lane and use an enormous external starter to ignite a methanol-fueled thunderstorm, firing the engine to life.

“It is a remarkable machine,” Letterman enthuses. “It is so beautiful.” The Watson’s Offenhauser provides a suitably impressive blare. The big four-cylinder doesn’t have the V-8 rumble of a stock car or the scream of a modern IndyCar, but it sounds purposeful.

Letterman remembers seeing a similar car up close as a boy. “But they wouldn’t let you touch it, and they wouldn’t let you get in it,” he says. “That was so frustrating. But it was a lesson in my life. I thought, OK, guys like me don’t get to sit in racecars.”

That was then. Two crewmen push the car to start it rolling—standard procedure for these racecars, because the transmission won’t shift into gear when the car is stationary.

Letterman gasses it and eases out on the clutch. Then he lets out the clutch a bit more—too much more—and the engine sputters. Letterman stomps the clutch pedal to try to save it, but it is too late.

The engine dies. But the Watson is still rolling. Letterman pops the clutch, floors the gas pedal, and takes off.

“I’m impressed,” says Speedway’s official historian, Donald Davidson. “It seemed like it stalled, and then he saved it. Not everybody can do that.”

To qualify for the Indy 500, drivers must do four laps, and their average speed over those four laps—10 miles around the 2.5-mile quad-oval—determines their starting position. Fittingly, as he completes his fourth lap, Letterman steers the Watson back into the pits.

Turns out he thought he saw some smoke and stopped out of caution. A bit of investigation shows the car is overheated. Coolant boiled out onto the engine, creating the “smoke” Letterman saw from the cockpit. Now there’s a small puddle on the concrete beneath the car.

The car is designed to move at top speeds. Apparently a first-timer might not be inclined to gun it the way a professional driver would, and so the car rebelled.

“I see smoke coming out of the damn car, coming between [turns] three and four, and I have the presence of mind to take it out of gear, turn off the ignition switch, coast from the fourth turn right down here, and stop perfectly,” Letterman recounts. “I like to think I prevented a conflagration.”

“Clearly, you succeeded,” I tell him. Letterman warms to the moment with the same wry, Midwestern wit that made him a television comedy legend. “Write that down then! Clearly! Nobody had to come get me. Clearly prevented a conflagration. That’s right! I wish they had told me that when the thing sounds like it’s gonna choke out, that’s when you gotta lean on it. But I was so scared. I was timid as a kitty. I was. I was timid as a kitty!”

As he steps out of the car, I ask him how the ride was.

“It was one of those things where, when you go to the Grand Canyon, you know, you’re driving and you’re driving and you’re driving, and you think, How good can it be? How great can it really be? ” he explains. “And then you get to the Grand Canyon and it’s, Oh my God! It’s better than I thought.”

His favorite part, he says, was the view from the cockpit. “You get to see everything. I guess that can be attributed to how slowly I was going. However, I did get to sit in it. And I got it out of the pits with a minimum amount of drama. That’s really all I care about.”

Letterman crouches to peer beneath the car for telltale fluids. “What’s this going to cost us?” he curiously asks the handlers, who are more accustomed than Letterman to simple headaches like overheated racecars. “Let’s pray to God Parnelli Jones never hears about this…”

I ask him for his overall assessment. Pretty cool?

“Yes, it was,” he replies, “and like so many other cool things in my life, I screwed it up. On the other hand, I’ve never done it before. I never thought I’d get to do it.” He flashes a crooked smile familiar to millions of television viewers and adds, “Nobody in their right mind should let me do this.”