DaveWatch: Countdown to Letterman’s Last ‘Late Show,’ Day 8

“We are not going to Montana!”
Monday night’s Late Show was a memorable one, indeed, punctuated by a round of free milkshakes for the studio audience (thanks to another second place finish by Graham Rahal’s Steak ‘n Shake Indy car this past weekend), an exploding klieg light that sent an unexpected shower of sparks down on Paul Shaffer, and what appeared to be an unscripted onscreen burp from the host himself.
Dave handled all of those interruptions — as well as the cleanup of some shake spillage on his desk — with genial good humor, even suggesting that the exploding light was a message from the late Ed Sullivan. To be fair, he wasn’t sure if the theater’s former occupant was telling Paul not to go, or attempting to hasten his exit.
But even our host’s famed poise was no match for a full-frontal assault from Howard Stern, who made his final appearance armed with a copy of Rolling Stone‘s Letterman cover story — and who hectored Dave mercilessly about the article’s assertion that he was retiring to Montana. “We are not going to Montana!” Dave insisted, but Howard didn’t buy it for a second. “This sounds like the worst retirement ever,” he groaned.
The “King of All Media” briefly turned his attention over to Shaffer, bugging the bandleader to doff his ever-present sunglasses. “I think it’s time for truth — the network can’t do anything, we don’t care about our image anymore — tell ‘em why you wear the dark glasses every single show. Tell ’em how high you are right now!”
Dave appeared to immensely enjoy the exchange between Stern and Shaffer (who eventually revealed his not-baked-looking eyes to the cameras), but he was soon back in the crosshairs of his guest. Howard surprised Letterman with an actually-pretty-decent flower painting that he’d done for Regina, Dave’s wife, as a consolation prize for having to live out her husband’s retirement years in big sky country. “Holy crap!” the host marveled. “Am I the only person stunned that he can do this?”
After enduring more shit-talk from Stern about Montana and his hermit-like tendencies, Dave turned the tables on Howard by dissing the radio star’s wardrobe — “I didn’t realize it was Carnaby Street night,” he cracked. Then, as Howard walked out onto the stage to better show off his ensemble, Dave playfully grabbed his guest’s hand, kissed it, then grinned into the camera like a naughty schoolboy. Of course, Stern then responded by grabbing him and attempting to plant a kiss on his lips. “Kiss me! Kiss me!” he demanded. “No!” refused Dave, squirming like the well-dressed dandy was giving him a rope-burn on the playground.
It was a beautifully spontaneous moment of televised silliness, and things got even more ridiculous when Don Rickles joined the party. The insult comedian, who turned 89 just a few days ago, was still more than sharp enough to hold his own, and he fired invective at both men separately and simultaneously. Even in his new cowboy hat — another Montana-inspired present from Howard — Dave looked like he’d died and gone to comedy heaven, laughing uproariously at the three-way chaos triggered by Rickles’ presence.
The only bummer about the episode was that it had to come to an end. If such Top 10 New Fall Shows like Mob Dermatologist and Albania’s Next Top Albanian don’t pan out, we’d like to suggest My Dinner with Dave, Don and Howard as a mid-season replacement. You know, if Dave doesn’t go to Montana.