David Letterman Returns to Late Night to Roast Jimmy Fallon

Letterman and a fistful of tortillas fulfill every ‘Tonight Show’ viewer’s fantasy
David Letterman Returns to Late Night to Roast Jimmy Fallon

David Letterman never realized his dream of taking over Johnny Carson’s Tonight Show. But at least he got to do the next best thing, returning last night to tell Jimmy Fallon how badly he’s botching the job.

The occasion seems to have been Paul Shaffer calling in a favor. Shaffer and the World’s Most Dangerous Band, Letterman’s longtime sidekicks, are filling in on The Tonight Show this week as the Roots prepare for the Saturday Night Live anniversary concert. But Shaffer himself isn’t sure how he got roped into sharing a stage with Fallon. “You ever take too much Ambien and then you wake up somewhere with no clue how the hell you got there?” he asked.

“Wow,” Letterman replied. “You’ve been reading my diary.”

After first mistaking Fallon’s Tonight Show for the 23rd hour of the Today Show, Letterman took a few minutes to stick it to his younger counterpart. “Jimmy, by the way, congratulations. This is fantastic,” he began. “I’m telling you, this is perhaps the greatest rehearsal I’ve ever been part of.”

When Fallon assured him this was the actual show, Letterman noted that he and Shaffer once did a similar program back in the day. One notable difference: “We didn’t do the Chuck E. Cheese crap.”

Fallon then offered Letterman the chance to tell some jokes. Letterman agreed to take a look at Fallon’s punchlines, with Roman the Cue Card Guy allowing Letterman to see which gags he liked best. After silently reading through all of them, Letterman passed.

If the jokes won’t work, Fallon suggested, how about they make a viral video? Letterman expressed mock delight at the idea, his chuckle dripping with disdain. Fallon handed a phone to Shaffer and then acted out the Handshake Challenge — hopping over to Letterman for a handshake then bouncing back out of frame.

“That was lame,” Letterman noted. 

He wasn’t lying. So he offered his idea for a TikTok sensation — he’d smack Fallon in the face with a tortilla. And honestly, who wouldn’t want to do that? Fallon hemmed and hawed but you see where this is going. 

POW! Letterman really let Fallon have it, fulfilling a fantasy for many a Tonight Show viewer. At least Fallon was ready for the first blow — Letterman’s subsequent savage backhand seemed to take Fallon by surprise.

“You keep slapping me,” said Fallon, master of the obvious. 

POW. “You’re only supposed to do it once!” Fallon whined. POW. This looked like the most fun Letterman had had in a long, long time. After a short lull, he caught Fallon by surprise with a fifth blow, an audible SMACK that could be heard throughout 30 Rock. As an added bonus, Shaffer hopped down from behind the keyboard to give Fallon another couple of slaps, but his effort lacked Letterman’s vicious, violent glee.  

After all the indignity, Letterman agreed to let Fallon have one swing. The younger comedian clearly pulled his tortilla punch, leading a disgusted Letterman to joke, “I think you cracked a crown.”

And with that, Letterman waved goodbye to the crowd. After a big round of applause, Fallon assured the audience, “I didn’t hurt him! He’s fine!”

From somewhere backstage, we heard Letterman’s voice one final time: “I’ll see you in court, (bleep)er(bleep)er!”

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