Letterman’s Last Show: Assessing His Landmark Career

The first time I sensed David Letterman would revolutionize television was when I saw him with Mr. T. This was back in 1982, not long after he had begun hosting Late Night. The experimental program proved the perfect showcase for Johnny Carson’s smart-aleck disciple. Letterman was interviewing Mr. T, who was turning heads thanks to a breakthrough role as heavyweight Clubber Lang in Rocky III. Mr. T had won the world’s toughest bouncer competition, but it was difficult to tell if his bravado—gold chains, Mohawk, work boots—was a clever put-on or something authentic.

“If you see me squeeze this ball over 10 times, that means cut the jokes. I done squeezed it six times already,” Mr. T told Dave, scowling.

“That’s why I’m squeezing this ball, so I won’t get too mad,” Mr. T said on the show that night, scowling as he held up a small black racquetball. “If you see me squeeze this ball over 10 times, that means cut the jokes. I done squeezed it six times already.”

Letterman glanced at him, whipped out a pencil, and pretended to take a note while shouting to his producers: “We’re up to six!”

I was hooked.

Letterman had been on my radar for awhile. As a high-school comedy nerd with a penchant for staying up late, I had watched him build his career as a comedian with guest appearances on Carson’s show. Growing up in Gary, I also knew he was a fellow Hoosier. But Late Night was different from his previous work. It was, quite simply, unlike anything else on TV.

Fueled by an oddball love of subverting television conventions, Letterman held elevator races with play-by-play by Bob Costas. Where Carson might indulge comfortable banter with his guests, Letterman seemed to enjoy pushing celebrities into uncomfortable moments. Cher famously called him an “a—hole” after repeated questions on why she hadn’t come on the show earlier. Madonna also feuded with him on-air. At a time when most TV talk shows were safe, choreographed showcases for celebrities to sell themselves, Late Night offered the possibility of seeing something real.

As an Indiana boy, I also liked that he tried to help fellow Hoosiers. In college, I was in a band that opened for Henry Lee Summer several times, building friendships with his musicians. So it was inspiring to see Letterman bring Summer on Late Night to play his 1988 hit single, “I Wish I Had a Girl.” Later, Letterman gave a break to a young comic from La Porte named Jim Gaffigan, handing him the starring role in Welcome to New York, developed by the host’s Worldwide Pants production company.

When Carson retired in 1992 and NBC passed over Letterman to pick Jay Leno as The Tonight Show’s new host, Letterman moved to CBS and turned the Ed Sullivan Theater into a permanent home for his antics on the Late Show. I attended a taping in his second week at CBS—I was working for a newspaper in New Jersey at the time—and was struck by how much more professional this new show was. Headquartered in the theater where The Beatles first met an American TV audience, with a sprawling studio and well-honed band, Letterman had joined a respectable pantheon. The eccentric upstart had become an institution.

In my 18 years of covering television, I met almost every late-night television host, but I’d never met Letterman until this month. That’s a measure of how little he talks to press, but also an example of how he simply refuses to play by the same rules as others. While many TV personalities might glad-hand critics, Letterman lets his work do the talking.

Over a landmark career, Letterman has been a man of contrasts: a New York talk-show host who always remembered his Indiana roots; a smooth performer who built a show on eccentric gags and disquieting moments. But there won’t be much contrast among the retrospectives when he retires on May 20. Critics will sum up his achievements with a phrase that’s the ultimate compliment for a trailblazing broadcaster: There will never be another quite like him.