David Letterman stuck his penis in things. Also, something about extortion.

October 2nd, 2009 // 73 Comments

David Letterman candidly revealed on his show last night that he was involved in a sting operation to stop a $2 million blackmail/extortion plot revolving around affairs he had with staffers, according to PopEater:

“In the back seat of my car, there’s a package that I don’t recognize. What this is is a guy is going to write a screenplay about me and he’s going to take all the terrible stuff that he knows about my life and he’s going to put it into a movie unless I give him some money,” Letterman explained to the audience.
“Now of course we get to what is it. What was all the creepy stuff that he was going to put into the screenplay and the movie, and the creepy stuff that I had … sex with women who work for me on the show. Now, my response to that is yes, I have,” he continued.

CBS has confirmed the extortionist was a former 48 Hours producer Joe Halderman who RadarOnline reports lived with one of the staffers Letterman had sex with:

The affair happened a long time ago, before his son Harry was born, and before he got married, but he was living with his wife to be at the time.
Halderman needed money police say and decided to target Letterman.
The woman still works on the show but is no longer involved with David.

You know what the worst part about this whole ordeal is? I keep envisioning Paul Shaffer standing there with a keyboard during each romantic interlude:

And that’s Dave coming, that’s Dave coming, that’s Daaaaaaaave coming.
Now go call a cab. Doo waa!

Photo: WENN

  1. Another 0ne bites the Dust

    What a DumbAss!


    GOD gave men TWO heads..and brains only enough to use 0NE.


    Just like him.

  2. Letterman the Ass

    So true #51. Some men can keep their brains in their pants, and some can’t.

  3. Ouch!

    He would’ve been better off..Shoving his Penis into a Bee Hive.

  4. CakeGirl

    I wish people would stop acting like sex is a big, scandalous deal. And stop using Clinton as an example of the Big Bad Sleazy President Who Had an Affair. I bet every president since Washington has grabbed the poot, he just got busted. I’m not slamming men – I love them, and I value a monogamous relationship, but I think men are wired differently than women. Why do men cheat on beautiful women? Because it’s available. Separately, I’ve watched his show since the early 80s (when he was funniest and weirdest on NBC) and even saw him filming a segment in 85 near my high school. He was wearing shorts and had great legs and if I worked with him I would’ve done him too. A man of power is irresistible to women, so it takes two. No, you’re not supposed to screw around in the office but it happens over and over. I doubt he had a gun to anyone’s head. His private life is his private life.

  5. holy balls people how complicated is this…

    you don’t shit where you sleep
    you don’t fuck where you work

    it’s not rocket science.

  6. Turd

    Hey CakeGirl, come on over and get some of my white icing for your cake

  7. Kimberly

    I love how people are laughing (but probably out of embarrassment) when his wife is probably at home crying and locking herself in her room.

  8. Ms.Whiplash

    I wonder if there will be an awkward pause the next time he makes a snide, smug remark about a politician or entertainer caught up in a sex scandal….. it just makes him seem like such a hypocrite. I hope his wife is kicking him in the balls right now for the embarassment he’s brought on their family. Oh well, it’s his private business, but he’s dropped a couple of notches in my opinion.

  9. Unlike women, men do not readily discuss personal medical conditions and disorders with their friends. It is for this reason that pearly penile papules are very misunderstood.

    It is not surprising that you would be plagued by worry and paranoia at the appearance of a bump on the rim of your penis. Immediately you would suspect venereal disease or even worse, cancer. The likelihood is that you do not have either, but rather a simple case of pearly penile papules. Pearly penile papules are very common among men, especially uncircumcised men. They are not as a result of bad hygiene and are not contagious in any way whatsoever. Many men actually find that they appear and disappear without any treatment at all.

    However, if you are feeling uncomfortable with them, they can be effectively removed with a simple treatment of radiofrequency surgery. You should however consult your doctor and have them seen to should they emit a discharge or are physically painful.

  10. OhHaiThar

    David Letterman has sex, stop the fucking press. NEXT.

  11. The Voice Of Reason

    ATTN: All Women

    Men like to have sex. It’s never going to change. There isn’t any amount of social pressure, or guilt tripping that is going to alter our psychological destiny.

    It’s what we’re here to do.

    Women are hear to nag and hiss when it’s confirmed that men like to have sex with different women. Ultimately, most men understand that women will never understand, so we keep it to ourselves.

  12. ham

    @61- not all. Some people, both men and women, are asexual and never consider that at all. Like most biological traits, sex drive is distributed in the bell curve fashion and changes with time/ hormonal balance. Thereafter, culture, society comes into play, too.

  13. The Leech

    I bet Elliot Spitzer is drinking champagne right now…

  14. Ms.Whiplash

    61- I actually kind of agree with your massive, sweeping generalization. A LOT of guys seem to want to just screw anything and everything. No doubt about that. But, why do these guys get married and have families? Seems really cruel to me. Why not just stay single and have sex with every intern, assistant, student or whatever they want? There’s lots of women out there who think like that too. Or, at the very least, why don’t these guys get smarter, and figure out a way to do it without getting caught.

  15. sunshine

    Fart Bucket – #56 – You are spot on and freakin’ hilarious!

  16. While CNN and various outlets work overtime to overhaul Letterman’s image, I think Dave is done. Why? Because Letterman is a comedian, and at the end of the day, all this blackmail stuff isn’t funny and it isn’t cool. And, it tends to stick in peoples minds. They ask questions. The last thing any comedian or anyone on any stage anywhere wants to ask their audience: what are you looking at?

  17. titsonsnack

    #61 I feel really bad for you. What kind of sad sex life have you had? What kind of frigid women do you hang around with?

  18. The Voice Of Reason

    I have an active sex life. The puritanical outlook that most Americans have towards sex is not only unnatural, but it’s repressive, and it only increases the fixation.

    In comparison, Europe has fairly liberal views about sex, yet their societies are not on the verge of collapse. Americans treat sex like cloistered nuns, when in reality, they know as well as anyone what goes on behind closed doors. It’s a false persona.

    You cannot turn around such embedded nature. Not all men rationalize it that way. They think their feelings are changing. They think that they really are falling in love with someone else for all the right reasons. However, the underlying cause is seed spreading. It merely gets recast in the human mind as something more complex, and romantic. We intellectualize fairly straightforward behavior to hide our natural superficiality.

    Even if Dave did such things while married, or in a relationship, it simply makes him human, not a monster. The clean up is between him, and the relevant parties, not some obsessive females who put themselves on ice over the threat of male wanderlust.

    Married men often cheat because they’re trying to address an urge that is overwhelming to them. The marriage may be dull, and past it’s point of value, yet the feelings for the person still remain. It’s rarely ever as simple as a man being arrogant, and diabolical. They are likely struggling with severe guilt, and disappointment with themselves. A married man might rationalize that engaging in such behavior will ultimately preserve their more meaningful relationship, while the affair might temper their constant lust. If you’re not a man, then you probably won’t understand. It’s all just chimp behavior to women.

    No doubt, feelings, and relationships are hurt, but at no point in history has the struggle ever been any different. Even in religious societies, it was assumed that men would have women on the side to purge such urges. This can be seen today by the high rates of infidelity in religious communities. I would say that the temptation is even greater in such communities.

    All in all, relationships, especially with modern lifespans, are difficult to manage. Whatever indiscretions occur should be between the parties involved. Destroying people’s characters over it is a bit diabolical.

    Finally, to all of the women who think they have some devoted shclub to cuddle with at home, sure you do. You have that man until he is given options. Most men don’t have options. They’re not especially attractive, influential, or wealthy, so they speak righteously about their sexual discipline to increase their social cache. They don’t want to be alone, so any relationship is a good relationship, until, you guessed it, their options change.

    Under the right circumstances, anybody is capable of anything.

    Monogamy is a fairly recent invention in the human world, and it has failed miserably on all accounts. Even married people often have kids, raise them, and then look for new horizons. Their duty is done, and life is short. They may not expect this change in thinking, or even desire it, but they don’t have much control over it, and often they do the best that they can.

    The fact that divorce rates are so high, and the dependencies found in traditional relationships no longer apply, it’s little wonder why it’s so common for even fairly bland individuals to be caught with their hand in the cookie jar.

    Considering the circumstances, Dave handled the situation with as much dignity as a person could.

  19. Ms.Whiplash

    Yawn…..wow, that was a lot of words, #68. Way too many for a place like this. I did manage to skim it for an overview, though. I’m sure that essay would have got you an A in a sociology class, maybe even biology or psychology. You seem to know what you’re talking about, and it’s obvious how you live your life. I just think you’re generalizing way too much, and not making allowances for differences in personalities or cultures. I feel sorry for Dave’s wife and son. His foolishness will damage them all. Should have just gotten divorced, Dave. Or never married in the first place. Who knows, maybe they have an open marriage. Good for them, but jeez, a little more discretion please!

  20. Gary

    I would have bet it all that the Grinder Girl and the Hula Hoop Girl were involved.

  21. I would have bet it all that the Grinder Girl and the Hula Hoop Girl were involved.

  22. Wait, so David Letterman is not a perfect gentleman, people actually care about the Kardashian sisters, and Miley Cyrus makes money singing live music???? Is this Armageddon?!?!

  23. stenia nordstrom

    Yes Letterman is never quiet, for example, his latest personal preference (love?) is reported to be Joe (“the goofy boy”), employed as a writer and also used in comical sketches.
    After famous Letterman’s affair with a female employee…life goes on :-)

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