That was the question many were debating Friday, the day after the CBS "Late Show" host revealed to his audience that he had sexual relationships with female employees and had been the victim of an extortion attempt to keep that information private.
Letterman unraveled the sordid story his way Thursday night, with humor, honesty and self-effacement. He may have endeared himself to some fans, but his likeability has been thrown into jeopardy. Reaction poured in Friday across the Web.
In the comments sections of YouTube videos, the dialogue was two-sided as some came to Letterman's defense, while others were critical of him.
Various jokes used Letterman's production company for a pun: "Dave, keep your `World Wide Pants' on." Some called him a "pervert." Others applauded Letterman for taking responsibility and "manning-up" to the alleged extortionist.
Similar lines were drawn on Twitter, where Letterman was one of the most tweeted-about subjects. He evoked both sympathy and disgust.
Referring to Thursday's studio audience, which laughed through parts of Letterman's somewhat comical telling of the story, New York Times columnist David Carr tweeted: "Aw, now Letterman is his own punchline. Yuck."
On YouTube, videos of different woman who have worked on-air at the "Late Show" were circulating. Most were of Stephanie Birkitt, the sometimes on-air assistant who lived in Norwalk, Conn., with the alleged extortionist, Robert J. "Joe" Halderman, a producer for the true-crime show "48 Hours."
For several years, Birkitt regularly appeared on the "Late Show," often aiding Letterman in his audience interactions. Videos of her cameos circulated widely as the Web sought glimpses of her.
Ben McConnell, a marketing expert and author, blogged that Letterman had gotten in front of the story "in this Twitter-driven world." He wrote: "Letterman has certainly neutralized far worse rumor-mongering that could have quickly spiraled, jeopardizing his reputation, maybe even his job."
Like many blogs, Gawker.com was trolling through "Late Show" archives to find evidence of hypocrisy in Letterman's various jokes about infidelity through the years. Gawker wrote that the 62-year-old host was "haunted by the ghosts of Monica Lewinsky jokes past" and linked to old videos and top 10 lists of the "Late Show."
Other sleuthing was going on, too, as those following the sordid story looked for information on the less famous players involved. Halderman's Facebook page (which features a photo of him lounging in an Adirondack chair) had its personal information deleted.