If you didn't think Keith Olbermann could get any more insufferable, then you didn't watch his appearance on the Late Show with David Letterman last night. While he admitted, "I screwed up. I screwed up really big on this," and "It’s my fault that it didn’t succeed in the sense that I didn’t think the whole thing through," he discussed his $10 million/year salary (part of a $50 million/5-year contract he wants Current TV to commit to), "I didn’t say, ‘You know, if you buy a $10 million chandelier, you should have a house to put it in.' Just walking around with a $10 million chandelier isn’t going to do anybody a lot of good." more ›

First Lady Michelle Obama was on the Late Show with David Letterman and discussed a number of topics, from her father's struggle with MS to Bo, the adorable First Dog. Letterman pressed her about private chats with the President as well, "Now, you don’t have to answer this question, but this is the thing that I was thinking about. I have conversations with my wife. Paul has conversations with his wife. Married men and women have conversations all the time… Hypothetically speaking, at the end of the day, has your husband ever come home and said to you, ‘Oh, that John Boehner -- what an idiot’?" more ›

Earlier this week we took a look back at some of David Letterman's more interesting (and shirtless) moments prior to his 30th year anniversary in late night television. Letterman is now the longest-serving host in late-night TV history. That milestone was reached last night, and the host celebrated on-air with his pal Howard Stern, who says he's the only one still fighting the late night war. Watch below as the two talk about Jay Leno, complete with an impersonation from Letterman himself. more ›

Tomorrow night will mark David Letterman's 30th year anniversary in late night television, though not always with the same network. He started out as the host of NBC's Late Night With David Letterman on February 1st, 1982, and left a little over a decade when he made his shift over to CBS in 1993. According to the Late Show's executive producer Rob Burnett, the milestone may be mentioned on tomorrow night's show, "but I don’t see an extravaganza coming to fruition. Dave has never been super comfortable drawing a lot of attention to himself." Howard Stern is a guest on the show tomorrow night, who Burnett refers to as "a kindred spirit with Dave." more ›

As you are well aware by now, the first New York City Steak 'N Shake opened yesterday to big crowds. But it wasn't just plebs looking for free food who stopped by. No less than David Letterman—who films his show so close to the new restaurant he says the building has "smelled like grilled onions" all week—went too. Well, he sent his camera over to order one and then ate it on the air: more ›

Take that Leno! David Letterman is reportedly close to a deal with CBS that would keep the 64-year-old as the Late Show host until 2014—which would make him the longest-running late-night star in TV history. Less certain is the fate of Craig Ferguson, whose hilarious and incredibly low-budget Late Late Show airs after Letterman. Wonder if the arrival of Steak 'N Shake in the Ed Sullivan theater will help seal the deal for the Indiana native? more ›

Remember, just a few months ago, when Tracy Morgan was at the center of a pretty serious sh*itstorm over a nasty little homophobic rant during a stand-up act in Nashville? While he did issue a formal apology shortly after the incident, it turns out that people—like David Letterman—are still talking about it, much to Morgan's chagrin. more ›

Wilco's excellent return-to-form album, The Whole Love, is finally being released next week—but like us, you've probably already heard a stream of texture-rich album (and if not, it's streaming in its entirety on NPR). The band, who is playing Central Park tonight and tomorrow, made their way to the Late Show with David Letterman last night, and performed a 60+ minute show for web broadcast. You can watch the whole thing below (setlist after the jump), including standout takes on spiky new single "I Might," the jaunty lovelorn "Whole Love," and the two-part "Art Of Almost," which climaxes in a blistering guitar frenzy. more ›

There's been a whole lot of hoo-ha over Alec Baldwin's potential mayoral run, and he's not doing much to dispel the rumors. Baldwin stopped to chitchat with Letterman last night and explained that he'd like to "be" the mayor, not necessarily "run" for mayor. And why would that be? Mostly because of his smoking hot 27-year-old-yoga-instructor girlfriend Hilaria Thomas, who's introduced on-camera. more ›

Last night, David Letterman returned from his vacation and addressed the alleged Al-Qaeda death threat: "I have a fatwa on me. And they say the guy that issued the fatwa is an Internet jihadist. Internet jihadist, and I said, 'Well, heck, who says Obama isn't creating jobs?'" He also said, "We have a great audience night in and night out but tonight you mean a lot to me. You people are more than an audience tonight, really. You're more like a human shield." more ›

Has Al Qaeda targeted Late Show host David Letterman? According to an analyst from SITE, a private company that tracks extremist websites, it seems that way: they tell EW that a member of an Al Qaeda message board has posted an assassination threat against the comedian. Is it because his "intoxicating" sexuality is threatening them? more ›

Jimmy Whittemore may be sorry for drunkenly trashing the Ed Sullivan Theater, where The Late Show With David Letterman tapes, but now he's started a trend: Earlier this morning, a man was arrested breaking into the Ed Sullivan Theater. However, he only made it as far as the vestibule. more ›

Aspiring actor, midtown bartender and Ed Sullivan Theater-crasher Jimmy Whittemore says he regrets getting tanked and bashing the glass doors of Letterman's Late Show home. "I'm ashamed. I'm still bothered," Whittemore tells the Daily News, "I just want to apologize to the theater people." After hitting the town and the bottle for a night of karaoke, he claims he had no idea what had happened until he was arrested. "I just wanted to go out and do karaoke…Next thing I remember is laying down on the floor, surrounded by cops." As if you needed another reason: karaoke is evil. more ›

If you've got small children in the room, you should get them away from the computer screen immediately, because this surveillance video of a shocking, violent "rampage" in the lobby of the Ed Sullivan Theater is NOT for the faint of heart. Since Sunday we've been hearing about this "rampage," but nothing could prepare us for the graphic nature of this footage. Be warned: A garbage can is knocked over, a door is brutally kicked, and [SPOILER!] at least four defenseless velvet rope stanchions are hurled SAVAGELY to the floor. After watching this senseless wave of destruction, we can only salute David Letterman for his courageous decision to even broadcast his program tonight. more ›

Details are emerging from yesterday's destruction of the Ed Sullivan Theater's glass doors, and it appears that the suspect, 22-year-old James Whittemore, was an aspiring actor who had hit a rough patch. Whittemore graduated from the AMDA in 2009, and worked in restaurants between stints at regional shows at the Tropicana in Atlantic City and the Six Flags in Massachusetts. Just two weeks ago, he was jumped near his home on W. 135th Street and had his nose broken. "Jimmy is a good kid with a bad life," his foster sister tells the Daily News. Whittemore's mother was allegedly an alcoholic who hung herself in prison, and his father is a homeless ex-con. His uncle tells the paper, "The demons just grow in our family like that." more ›

Early this morning a "blind drunk" man shattered the glass doors of the Ed Sullivan Theater in Midtown, entered the lobby and flipped over trash cans, making a mess of the home of David Letterman's Late Show. Police responded to a 911 call around 7 a.m. and arrested 22-year-old James Whittemore, who had a cut on his face and was later taken to the hospital. There are more constructive ways to express your disappointment that LiLo pulled out of an appearance. more ›

Noted motivational speaker and snack enthusiast Rex Ryan turned up on The Colbert Report last night to talk about his new memoir, "Play It Like You Mean It." You can watch the interview below, including this gem: "You ever look at a sunset and say, 'I'd like to see somebody tackle that'?" more ›

Did David Letterman just pull a Regis and announce his retirement last night? Maybe! During a chat with Howard Stern the shock jock asked the late night host "how much longer are you doing this, really?" To which Letterman responded "I don't know. Maybe two more years?" more ›

Last night Joaquin Phoenix was face-to-face with David Letterman again after not appearing on the show since this happened last year. He was clean-shaven and apologizing (sort of) for the last time he was a Late Show guest. They both claimed Letterman himself was not in on the hoax, and the actor told the host, "You've interviewed many, many people and I assumed that you would know the difference between a character and a real person, so—but I apologize. I hope I didn't offend you in any way." more ›

Last month word came out the Michael Douglas was battling throat cancer, at which time he said he was optimistic about a full recovery. Now as he makes the press rounds promoting his latest role in Wall Street II, he's talking about the battle some more. more ›

The news producer who pleaded guilty to trying to blackmail David Letterman for $2 million was sentenced to 6 months in prison and 1,000 hours of community service today. According to the Daily News, "To wile away the months, Halderman brought along a Bible and a thriller by Stieg Larsson called 'The Girl Who Played With Fire.'" His lawyer Gerald Shargel said, "He's been to every hot spot in the world, Iraq, Afghanistan, Somalia. I think he can handle Rikers Island." more ›

“Sneaky Chef” author Missy Lapine is taking another stab at Jerry Seinfeld, claiming he slandered her character by calling her a “nutjob” on national TV. In a previous lawsuit Lapine accused the comic’s wife of stealing her idea for a cookbook that showed parents how to covertly feed their kids healthy foods (sweet potato in a grilled cheese sandwich, avocado in chocolate pudding etc.). A judge ruled against her but nonetheless Seinfeld felt compelled to call her a “wacko” during an appearance on David Letterman. According to the Daily News, the new suit targets the statements made by the sitcom star as well as Harper Collins, who the author says twice rejected her cookbook concept, before handing a book deal to Seinfeld’s wife. more ›

Robert "Joe" Halderman pleaded guilty yesterday for his attempt to extort $2 million from David Letterman by way of revealing Letterman's many affairs. The former CBS News producer admitted his scheme to sell a movie treatment to the talk show host "was just a thinly-veiled threat to ruin Mr. Letterman if he did not pay me a lot of money." more ›

The former CBS News producer who was accused of trying to shake down talk show host David Letterman for $2 million is set to plead guilty, according to the Daily News and Post, which reports, "Robert Halderman, a '48 Hours' producer, is expected to be sentenced to six months in jail, as well as ordered to do 1000 hours of community service and serve four-and-a-half years probation, as part of the agreement with prosecutors to plead guilty to second-degree larceny in Manhattan Supreme Court today." more ›

A new Vanity Fair article takes a deep look into the Letterman extortion scandal, and what it finds out is kind of weird. It turns out that 62-year-old Letterman has a certain "electricity" that drives many female staffers crazy. “It’s like a cult,” says one former insider "It’s like Jesus Christ saying, ‘Hey, let’s go to dinner!' You’re going to go, ‘Wow! He chose me!’" more ›

Yesterday Jay Leno issued his own open letter to the People of Earth, and even though it was just a parody, we imagine it wouldn't be far off from what the man himself would have to say. Which would be nothing in comparison to Our Hero Conan O'Brien's letter. But the big news today is Conan is leaving NBC. According to Bill Simmons, at least, "Next week is Conan's final week hosting the Tonight Show. His staff is trying to book big guests so he goes out with a bang. It's true." more ›

Last night, Our Hero Conan O'Brien delivered his monologue on NBC's Tonight Show just hours after sending out a statement questioning that same network's choice in reshuffling their late night hours. He was rightfully applauded by many yesterday for declaring he would not stay on as host if the legendary time slot was pushed, as well as for the class he exhibited in delivering that news. (He even broke down talking to his staff, who have been with him since the beginning.) more ›