David Letterman & Cigars

Cigars and comedians have had a long and loving relationship. George Burns, Milton Berle, Groucho Marx, Bill Cosby and Ron White, among others, all used cigars as props. One who had to sneak his puffs while on the air was David Letterman, one of Cigar Aficionado’s “Top 100 Cigar Smokers of the 20th Century,” ranking number 36.

David Letterman’s Favorite Cigar

Famous for his “top 10” lists on his Late Night show, Letterman never gave us “David Letterman’s Top 10 Favorite Cigars.” We know he loved large Cuban Cohibas. Before 1998, Letterman would smoke up to 20 of them a day.

Make It a Late One

David Letterman was born April 12, 1947, in Indianapolis, Indiana. After graduating from Ball State University in 1969, Letterman began his broadcasting career on the college’s student-run WBST radio station but was fired for his desecration of classical music. His unpredictable and humorous on-air antics drew attention during his stint as a weatherman on an Indianapolis television station. Encouraged by friends and family, Letterman moved to Los Angeles in 1975 to pursue a career in comedy where he worked his way up through comedy clubs. His sarcastic wit eventually earned him a regular guest spot on The Tonight Show Starring Johnny Carson. On February 1, 1982, Late Night with David Letterman debuted on NBC. When NBC executives chose Jay Leno to replace Carson over Letterman on The Tonight Show in 1992, Letterman departed for CBS where the Late Show with David Letterman continued for more than two decades, earning historic household acclaim.

Smoking On the Air

If you watched Letterman hosting his show on CBS, you’d notice occasionally that he would reach for his cigar, hidden behind the desk, when going to a commercial break. That’s when he would smoke. Sometimes, when the ads were over, Letterman was still taking a puff before scrambling to hide the cigar. On one occasion, in 1994, the now-late first lady, Barbara Bush, elegantly suggested Dave give up smoking.

Madonna Sets the Show on Fire

In March of 1994, the Late Show with David Letterman had Madonna on as a guest. The show was one of Letterman’s highest rated ever. Madonna said the F-word 14 times during the interview. Letterman urged Madonna to kiss a guy in the audience. She didn’t. Then she called the host “a sick f**k.”

“You realize this is being broadcast, don’t you?” Letterman responds.

There are references to Madonna’s underwear and sex life. Then she lights up one of Letterman’s Cohibas and puffs away. Back from commercial, Letterman says, “Madonna and I are just sitting around, smoking cigars, swapping recipes.”

Then, Madonna just doesn’t want to leave. When she finally does, Letterman wraps up the segment saying, “Okay, coming up in the next half hour, Mother Teresa is going to drop by,” later adding, “Well, I see we’ve been canceled. There is no show tomorrow night.”

Letterman Quits, Then Un-Quits Cigars, Then….

At one point before 1998, Letterman gave up smoking. He regretted it.

“When I stopped smoking cigars it was the biggest mistake I made in my life,” he shared. “So, my resolution for ‘98 is I’m going to start smoking cigars again. I gave them up about a year and a half ago, and I now realize that it may have been my one last fun, interesting thing to do.”

In January of 2000, Letterman went to see his doctor for what he thought was a routine checkup for a “slight heart condition” he had had for a few years. It required monitoring with regular medical visits. The day turned out a bit differently than Letterman expected. He was rushed immediately into surgery where he underwent quintuple bypass heart surgery.

While any connection between his cigar smoking and heart condition is unclear, Letterman apparently was a bit casual about taking his doctor’s advice that he cut back on smoking 20 cigars a day.

The Late Show Ends

After more than 33 years on late-night TV, David Letterman called it quits in 2015. The finale was among Letterman’s most highly rated, but still did not beat his longtime rival Jay Leno on NBC’s The Tonight Show. The two comedians had famously fought to take over the chair from legend Johnny Carson. Letterman lost the battle and ended up at CBS.

These days, Letterman, 76, is a husband and father and sports a large, white beard. For four seasons, 2018-2022, he hosted a Netflix show titled “My Next Guest Needs No Introduction.” No word yet on whether there will be a fifth season of celebrity interviews.

As for cigar smoking, there are conflicting reports that Letterman smokes occasionally or has completely stopped.