How he deals with the situation at hand on Monday, and the nights ahead, could prove to be a defining chapter in his long TV career. With any luck, it could clinch his recent ratings victory in late-night TV.
The intensely private Letterman surely didn't want to be swept up in this maelstrom, which he dropped on "Late Show" viewers last Thursday with his startling revelations of having sex with women on his staff _ a disclosure prompted by an alleged $2 million blackmail threat against him.
But the flood of attention was inevitable.
For a celebrity the caliber of Hugh Grant, publicity _ including speculation of career suicide _ was certainly unavoidable 14 years ago, when he was arrested with a prostitute on Hollywood's Sunset Strip. Very embarrassing. But then he retreated to NBC's "The Tonight Show" for image rehab.
Host Jay Leno wasted no time before asking his instant classic of a question: "What the hell were you thinking?!"
Grant's appearance vaulted ratings runner-up "Tonight" past Letterman's CBS "Late Show," a leadership position Leno held through his retirement from late night earlier this year.
Since then, Letterman has reclaimed a ratings edge over new "Tonight" host Conan O'Brien.
And now, Dave may have truly sealed the deal. With his masterful monologue last Thursday, he took control of a dicey situation. He promised his audience "a little story" and delivered in spades. He acknowledged his own past "creepy" behavior. He reminded everyone that he's a guy "motivated by nothing but guilt."
Seated at his desk, he single-handedly gave a TV performance to equal the Jay-and-Hugh moment. Implicit in everything Dave said about his own behavior was the unspoken question: "What was I thinking?"
It could be that Letterman's carefully calibrated act of self-disclosure has put him in the best spot possible to weather the situation _ and even to milk it. Beloved by viewers and critics for decades, he has abruptly freshened the vintage David Letterman brand.
A humorist who mocks the world while holding it at arm's length, Letterman has demonstrated he still has the ability to surprise even fans who thought they knew him thoroughly.
And he has everybody talking.
Consider the women of ABC's "The View" on Monday.
Joy Behar said Letterman "jumped the gun. Politicians should take a page from his book. He was smart, PR-wise."
Fellow co-host Sherri Shepherd called Dave "a standup guy."
But guest co-host Lisa Ling declared, "When you're the boss, you should keep your thing in your pants."
Then Shepherd suggested that maybe his workplace sex partner "really liked him."
"Come on," Ling scoffed.
And on it went.
Most of the audience members waiting to enter the Ed Sullivan Theater for Monday's "Late Show" taping were excited about being there and not so troubled by Letterman's personal life.
"He did a really classy job of announcing it to everyone," said Keely Ahearn, who came from Minneapolis with her friend Adam Melchert. "I don't think he should have to say that much about it."
Melchert said he understood that such attention is part of being in the spotlight, but said, ultimately, "it's his business. I didn't ever watch the show because he was a moral compass for me."
Meanwhile, a legendary late-night host has nothing but praise for Letterman's skill at crisis management.
"To me, it seems Dave Letterman's handling of this is impeccable," Dick Cavett said in an e-mail. "Brave, direct, and _ dare I say it? _ manly. He has set a real example here of exactly how to behave when assaulted in such a sleazy operation."
It isn't the first time Dave has shown finesse in managing a firestorm.
In June, he had a run-in with former Alska Gov. Sarah Palin over jokes made at the expense of her teenage daughter. He emerged from a tumultuous few days of protests and demands for his dismissal with a ratings jolt. And thanks to the dumb-luck timing of the flap, he also handily upstaged his much-hyped NBC rival just as O'Brien was taking over as "Tonight" host.
In another of his memorable TV performances, Letterman apologized to Palin and her family. But he has never stopped making jokes at Palin's expense.
To judge from last week's tour-de-force confessional ("I know what you're saying: 'I'll be darned, Dave had sex'"), Letterman will now be making more jokes at his own expense.
Associated Press writer Jake Coyle contributed to this report.