DaveWatch: Countdown to Letterman's Last 'Late Show,' Day 9

Ray Romano gets emotional and Dave Matthews Band gets nostalgic as we hit the single-digit mark until D-Day

Despite David Letterman's well-deserved reputation for crustiness, there's always been something genuinely heartwarming about the segments of his show that featured his mother, Dorothy Mengering. The genuine affection that exists between them has always been palpable, even beneath their innate Hoosier reserve; and Mrs. Mengering's dry wit and no-nonsense delivery has always made it pretty obvious where her son got his sense of humor.

Now 93 years old, Mrs. Mengering didn't make an appearance on Friday night's Late Show. But she was there very much in spirit, thanks to an endearing highlight reel assembled in honor of Mother's Day, which showed her baking pies with John Mellencamp; hectoring Hilary Clinton about getting her President husband to take care of Dave's speeding tickets; expressing her fondness for such low-rent brews as Colt .45 and Old Milwaukee, and other classic "Dave's Mom" bits from the past two decades. Maybe it was our imagination, but we thought we glimpsed a trace of wistful moisture in Dave's eye as he applauded the reel….

The most heartfelt display of emotion Friday night came not from Dave, but rather from guest Ray Romano, who choked up several times while recalling how doing standup on Letterman 20 years earlier led directly to the creation — by Worldwide Pants, the host's production company — of his massively successful sitcom, Everybody Loves Raymond. Dave staunchly refused to take any credit for Romano's success ("You're flattering me unnecessarily," he protested), even when Romano went "George Bailey" on him with a photo that included Romano's fourth child and three rescue dogs, none of whom would currently exist if it hadn't been for his fateful Late Show debut. "You give life!" he insisted.

If Dave seemed more than slightly embarrassed by Romano's effusiveness (and his declaration that May 20, the date of Letterman's last show, will forever be known as "The Day That Comedy Died") he did appear to get a kick out of a series of photos showing Romano kissing various actresses. If it hadn't been for him, Romano explained, he wouldn't have ever been able to smooch Sofia Vergara on camera — and even the sheepish host couldn't bring himself argue with such convincing evidence. Romano closed his appearance by wandering back to the spot on the Late Show stage where it all began; Dave followed him out there, and bade him farewell with an emotional hug and a very sincere "God bless you!"

Romano wasn't the only one waxing grateful and nostalgic on Friday night. The Dave Matthews Band, who'd made their network TV debut on a 1995 episode of the Late Show, delivered a stirring rendition of  "What Would You Say" — the same song they'd performed two decades earlier on the same stage. At the song's conclusion, an obviously enthused Letterman took the stage to congratulate the band and compliment drummer Carter Beauford on his custom Late Show/DMB jersey. Not willing to let Matthews and co. leave despite the lateness of the hour, Dave begged for "a little more" and was rewarded with a blast of "Ants Marching" as the show's closing credits rolled. Only eight shows left to go, but Dave simply seemed too lost in the groove to care.