There Was A Time When Jay Leno Was Funny — And A Surprising BFF to David Letterman

“He’s often called himself the funniest man in America,” says Dave Letterman upon introducing fellow comic Jay Leno to his Late Night audience back in 1983. And although Letterman is clearly trying to be goofy, the line is missing his trademark snark. That’s because well before the Late Night Wars turned Letterman v. Leno into a bloodsport, the two comics were unlikely BFFs.

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As young comics fighting for stage time at The Comedy Store, Leno was enamored with Letterman’s use of language, according to Jason Zinoman’s Letterman: The Last Giant of Late Night. “I remember noticing the way (Letterman) turned a phrase,” Leno said, admiring Dave’s well-crafted bits about blowhard newscasters. But Leno also knew that Letterman had a long way to go as a performer. “I think he learned some of that from me, and I learned his use of language.”

The two continued leaning on each other once Letterman became the host of Late Night. Newbie host Letterman was most comfortable with old pal comics, and Leno made dozens of appearances, making him one of the show’s most popular guests. “I was like Rickles to Dave’s Johnny,” Leno said at the time.

Here’s a typical Leno appearance of the time, a manic burst of comic energy that required much more effort and thought than Jay put into his last decade on The Tonight Show. He also maxed out Letterman’s props team that day, using not one but two prop-gimmicks to sell his jokes.

Leno walked out with the first, a cover for a collectors’ item record album. He turned it around to reveal “Paul Shaffer Sings the Best of the Penthouse Letters.” Leno got big laughs from Letterman and the audience by running down the LP’s tracks, including “Dominating Stepsister,” “One Leg to Stand On,” and the album version of “I’ve Been Spanked For Something I Didn’t Even Do.”

Jay stayed on for two segments, pulling out Prop #2 for his big bit — advice to young comics about how to get booked on Letterman. He yoinked an actual book off the set’s shelves titled “Late Night’s Big Book of Overdone, Hackneyed Comedy Premises.” It’s really advice for how not to get booked on the show as Jay turns to the chapter on the most overdone comedy premises:

• “What would happen if E.T. landed in my neighborhood?” 
• “Anything with McNuggets.” 
• “Can you imagine this guy (insert famous celebrity or sports figure) at home?”

But even back in 1983, we get a sense of the battles to come. Leno was in road-dog mode, revealing that while he hadn’t been on Dave’s show for about six weeks, he hadn’t been home either. That’s an existence that sounds terrible to Letterman, who toured clubs at one time in his comic life, “but not long.” 

“It’s not awful, Dave, for us comedy foot soldiers in the trenches,” Leno joked. “I”m not one of your big-time comedy generals with some cushy desk job.” 

Shots fired! Leno uses a single joke to foreshadow the Late Night Wars on the horizon. Then he calls it back when he and Letterman argue about whether Indianapolis has something called Speed Week. “Maybe that was just the hip lingo among the working-class road guys,” guesses Leno. “To an Armchair General like yourself, I imagine it’s the Big Race.”

General Letterman should have been looking over his shoulder — those foot soldiers in the comedy trenches are sometimes planning mutiny.