Friday, he may start digging somewhere else.
The two talk show hosts couldn't have been friendlier as Oprah made her long-awaited appearance on CBS' "Late Show with David Letterman," wearing an elegant ball gown with a purple sash.
The costume wasn't entirely for the Letterman show - "the television event of the decade," as he jokingly called it. Oprah was on her way to an even bigger event on her calendar: the star-studded Broadway opening of the play "The Color Purple," produced by Oprah in a theater across the street from the Letterman show.
Still, Letterman made the most of it, telling the audience "I've been sort of gruff, I've made jokes, and generally been a nuisance... so of course she wasn't eager to come" on the show, adding that he was surprised and pleased when his son was born to receive a gift from Oprah: a box of books – "Harry's Book Club" – for the baby.
"Which one was your favorite?" said Oprah, explaining that she sent the books because she was impressed by a new "sweetness" that seemed to come to Letterman with the birth of his son.
"You can't go wrong with 'Runaway Bunny,' can you?" said the funnyman, without missing a beat.
Getting to the heart of things – from the point of view of the tabloids – Oprah brought a gift, told Letterman that "I have never for a moment had a feud with you" and asked him to tell her "what had transpired" if there were some kind of feud she did not know about.
He didn't come up with anything, and neither did she, and the two moved on to more promising topics, including the health care crisis in Africa, where she is opening a school to train girls to become the future leaders of the continent.
"I can't believe you're this serious," said Oprah, who hadn't expected the opportunity to discuss one of her favorite topics.
He was entirely serious, a moment perhaps made possible by a last minute avalanche of Oprah-Dave jokes – of the self-deprecating variety – before bringing her out on stage.
"Oprah formed her own media empire, Dave makes his own hairpieces," he intoned, in a list of comparisons between the two. "Oprah's studio audience leaves with cars, Dave's leaves with hypothermia... Oprah was once honored as TV Guide's performer of the year, Dave was 23 down in the TV Guide crossword."
The Top Ten List - Of Messages Left On Oprah's Answering Machine - included warnings, purportedly from Julia Roberts and Regis Philbin, tipping Oprah off that Dave had a tendency to be "all hands" during the commercial break.
He scowled at that unlikely description, receiving the expected harvest of laughs.
But there were only smiles as he closed out Oprah's appearance by personally walking her out of the building, hand in hand, in a dramatic gallant promenade across the street to her big Broadway opening.
By Francie Grace