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15 Famous Howard Stern Moments We Can’t Unsee (Or Unhear)

Shocking

It seems almost impossible but Howard Stern has been with us on the airwaves, in print, and even on the big screen, since 1986. That’s over 30 years of us listening to and reacting to the biggest “Shock Jock” of all time. Although he wasn’t the first radio personality to use shock as his primary communication tool, he was and is certainly the best at his art. The FCC agrees- Various Stern shows have been fined a record $2.5 million over the years. No one else even comes close. You may not like his style, or his tastes, or even his “look” (the whole wild hair and sunglasses thing is a bit much) but you’ve got to respect his dedication and longevity. After all, this is a man who had a nationally syndicated morning show for almost 20 years that consistently beat out all of its competitors, including a stretch when it was the number one show in both New York and Los Angeles. The same man parlayed his syndication success on terrestrial radio (AM & FM, for the uninitiated) into a $500 million deal with Sirius, where he has been for over a decade. Yes, you read that right- $500 million for a radio guy. That’s some serious leverage.

In all those years as a Shock Jock, Howard has, of course, had many, many intense on-air moments. Whether they have been awkward ones, angry ones, completely inappropriate ones, disturbing ones, or all of the above at the same time (trust me- on his show it’s happened), there’s plenty of Stern material that we can never unsee (or unhear, for that matter). Here are 15 of the most famous ones. And remember- don’t listen to his show with your kids. Or Mom.

15. Columbine Comments

If you thought Howard’s comments about Selena were pretty brutal well, guess what? Yup, he was able to top them a few years later. After his 1995 debacle, Howard made bigger and worse headlines for his comments in the wake of the Columbine High School massacre. Columbine was, at the time (and unfortunately isn’t any longer), the worst school shooting in our country’s history. Two completely psycho gunmen, students of the school, killed 13 people and wounded 24 more. Hmmm, I wonder what words of wisdom Howard shared the next day? Well, in his infinite empathy, Stern went on a rant about how “There were some really good-looking girls running with their hands over their heads,” and openly wondered if the shooters had ever tried to have sex with any of them. Just to make it worse he also said, “At least if you’re going to kill yourself and kill the kids, why wouldn’t you have some sex? If I was going to kill some people, I’d take them out with sex.” Not many people appreciated his humor that day.

14. Hate For Leno

It’s a truism that sometimes the big dogs in the celebrity world have themselves a rivalry. It happens all the time in Hollywood, there are plenty of divas throwing shade at each other on Twitter all the time- actually, sometimes it seems that Twitter was invented for that precise purpose- and pro athletes are notorious grudge holders. No it should be no surprise that a big time talk show host who wasn’t on Howard’s birthday guest list would be involved in a nasty, ongoing spat with him. I’m talking, of course, about Jay Leno, who Stern just hates, hates, hates! In 2010, as Leno was nearing the end of his career as the host of massively popular The Tonight Show, Howard weighed in on his rival’s legacy, saying that the “mere mention of Leno’s name makes me want to vomit.” Hey Howard, why don’t you tell us all how you really feel?

13. Selena Scandal

If you remember Selena, then you know that the ‘90’s Tejano singer was universally beloved in the Hispanic community and that her shooting death shocked the whole country (and the world for that matter). She was so big that J-Lo became a huge star mostly because she played the singer in the biopic about her life. So, when something tragic like the shooting of a superstar happens, who do you turn to? Apparently not Howard, who started playing gunfire over her music on air, and then used a fake Latin accent to say, “Spanish people have the worst taste in music. … This music does absolutely nothing for me. Alvin and the Chipmunks have more soul.” Again, as always, just “Wow, Howard. Wow.” Needless to say, Howard P.O’d millions of people with his out there comments. There’s a shock for you.

12. When Howard Leaves For Sirius

I mentioned at the top that Howard got a massive deal with Sirius satellite radio back in October of 2004. Remember, this was when Sirius was just becoming what it is nowadays- satellite radio was still fairly new to most people and XM was still competing with them, not merging with them. It was an awesome display of public relations savvy as the satellite radio giant expanded their footprint, the same way Netflix is doing these days in the streaming world. But why did Howard leave the medium he had been so successful in? How about the little show he did with Rick Salomon, he of the Paris Hilton tape, where they talked graphically about sex. The fact that a caller used the most off-color word imaginable on air was just the horrible icing on a cake that caused multiple markets to drop Howard and made the FCC drop an almost $500,000 fine on his station.

11. 60th Birthday Show

Love him or hate him, and with Howard there’s no in-between, the guy has a knack for gathering talent to himself. So it’s no surprise that his 60th birthday party a few years back was the nexus of big-time, top-name entertainers that it was. Joining Howard for this memorable event was a guest list loaded with the biggest stars. In an amazing display of respect, Jimmy Kimmel, Jimmy Fallon, and the legendary David Letterman, all huge hosts in their own right, came on the show that day. Just in case that wasn’t enough for you, he also had a few little names like Lorne Michaels, Robert Downey Jr., Steven Tyler and even “Baba Wa-Wa” (Barbara Walters, guys!) herself “drop by.” Oh yeah, a few people called Dave Grohl, Jewel and John Fogerty provided the musical backdrop a show of this magnitude so richly deserved. Wow is the only appropriate word here, I think.

10. Love For The Leibowitz’s

So the Leibowitz brothers, Eric and Jeffrey, were identical twins who had a singing group, The Jesus Twins. Howard “discovered” them. Or maybe he invented them out of whole cloth or maybe it was all a come-on by the twins. Probably no one will ever know for sure but anything is possible in Howard Land. In any event, the twins were just about the most annoying thing to ever come across the airwaves from Howard’s show, which is saying a lot, and Howard loved them while everyone else hated them. He particularly liked their song “Feel My Ubiquity,” which was worse than its title. And that’s saying a lot too. No one who ever heard the song can ever unhear it. It will go down in the annals of the Stern Show as one of the most cringe-inducing moments ever. You do not need to hunt this down and hear it- trust me on this guys.

9. Artie And Sal Square Off

Two longtime sidekicks, Artie and Sal, had their own day in the sun when a seemingly innocuous argument went completely sideways on the two, causing a mutual escalation that was horrifying (in a good way) to hear. It started off with a Sal rant about Artie being “Too mean” about their prank calls, to which Artie retorted that the Stern show was about brutal honesty and to basically suck it up. Which, it in fact is, even if it’s often a dumb kind of honesty. Somehow this morphed into a full on Sal assault on Artie’s awful movie Beer League and an Artie rebuttal that Sal couldn’t even make a movie. The argument escalated to the point that everyone was screaming and Artie actually threw a cart at his opponent. There’s nowhere else but Howard Land that stuff like this happens. You can’t even make it up.

8. Puppet Theft

One of the biggest bits over the years on Stern’s classic syndicated show was the appearances of the Jackie and Gary puppets. Everyone looked forward to those moments, except for the people who had to interact with them that is. The Jackie puppet was infamous for being even more evil than Jackie himself, a seeming impossibility. The puppet was so antagonistic, in fact, that Conan O’Brien famously had a meltdown while the puppet verbally attacked him. The Gary puppet, in keeping with the act of Stern sidekick Gary Dell ‘Abate, was just stupid, dumb, dull and idiotic. The most iconic moment for these two weird puppets came when someone actually stole the Gary puppet during an appearance of his at an electronics store. As usual with Howard and his cohorts, it was all a setup by another sidekick, “Stuttering John,” to throw some serious shade at Gary and publicly mock him. Hmm, sounds familiar, doesn’t it?

7. Foul Ball

Over the years Gary has been the butt of more than his fair share of jokes directed at him. In fact, he’s been the butt of more jokes than should ever be directed at anybody. One legendary incident occurred when Gary, because of his celebrity as a Stern sidekick, was asked to throw out the first pitch at a Mets game. Gary, a lifelong Mets fanatic and even a youth baseball coach, was ecstatic. And then his big day came and he blew it big time, airmailing his pitch way, way over the catcher’s mitt. After being heartlessly reamed on the Stern Show, Gary went on Jimmy Kimmel Live and tried to redeem himself, throwing pitch after pitch to Kimmel, each one worse than the one that preceded it. Neither of these was necessarily a moment on the show itself but both are indicative of the Howard Stern-led weirdness these guys traffic in.

6. Pete Townshend Walks Out

Pete Townshend is a certifiable rock Legend, a guy who made Rock & Roll what it is today. It’s no wonder then, that when he appeared on Stern’s show, the guys took it a little bit (OK, a lot) too far. One of the cohosts began questioning Townshend about the “child entertainment stuff.” The guitarist famously went under an investigation into his habits that ended with him being exonerated- many people at the time thought the whole thing was a witch hunt. Having this brought up by some random, annoying radio guy did not sit well with the great guitarist, who stormed out of the interview. I know if I were rich and famous and had any real or imaginary skeletons in my closet I would not ever be going on Howard’s show. For once, Howard actually apologized to Pete and the matter blew over. That’s the true shocker, I think.

5. Aunt Jemima Joke

In case you haven’t noticed, Howard has a tendency to take things a little too far; to push the envelope, as it were. Hell, he doesn’t just push the envelope. He sets it on fire, runs it over and then blows it up. One of his most awfully awkward moments, one we can never unhear or see, came when he announced on air that the only time he ever came close to making love with an African-American woman was when he did you know what to a picture of Aunt Jemima on a pancake box. First of all, Howard, that’s definitely TMI (not that Howard cares much about that). Second, it’s TMI that is so very wrong on so many levels that it transcends the everyday, merely shocking antics of the radio jock, and goes right into “What the hell did he just say?” territory. You can never get that little speech back into the box, whether it’s a pancake one or not.

4. Jackie’s Apology

Everybody should remember Jackie Martling’s role on Howard’s show in the glory years of syndication. He was, after all, Howard’s head writer and also appeared on air all the time. “The Joke Man” and “The King of All Media” (both titles were self-appointed by these two) had a good thing going on for a long time, even if Jackie has opened up more recently that not everything was all love between them. But Martling’s purest moment of total Howard Stern-dom came when he unveiled an apology to his wife Nancy for frolicking in a bathtub in Philadelphia with Jessica Hahn while on location for the show. Jessica Hahn, as I’m sure everybody remembers, was famous for sleeping with Jim Baker, the Televangelist and then posing for Playboy. Jackie became even more famous for his awkward, awful public apology- it was to listen to both then and now. Awkward and awful moments seem to be a hallmark of Howard Stern shows, don’t they?

3. Crazy Pat Cooper

Pat Cooper was an old time comedian, one of those angry, Borscht Belt-types who often appeared on Howard’s original syndicated show in the ‘80s and ‘90s. His whole shtick was to go off on anyone and anything at the drop of a hat. In fact, Cooper was so good at working himself up into a rage that he would ask himself questions, not like the answer and start railing against himself. It was pure comedy gold and fit in perfectly on Stern’s show. He also used this routine against his own family, just lambasting anyone who stood in his way- his wife, his kids and even his own mother. So it should come as no surprise that Howard managed to get him worked up on air and then slowly dialed them up and had his entire family on air railing right back at the comedian. It was awesome, more than a bit unsettling and definitely a classic Stern moment that will never be forgotten.

2. Gary’s Lovesick Video

Another iconic moment on the show that we can never unsee or hear came when a video tape of Gary (who always got shade- always) proclaiming his love to a girlfriend who left him surfaced. Stern and the rest of the sidekicks were absolutely relentless in hounding Gary for the lovesick video that included sentiments like Gary’s personal life being only a two (because he lost her) but his professional life was a nine (meaning he was a good catch). The long video- almost 30 minutes- was actually almost never aired as it required a listener who had dated the same girl to figure out the connection and beg Howard to go after Gary. Not that it took much for Hard to do that. They aired the video after Howard and the listeners kicked in $18,000 for Gary to bring it in. For some guys, a prank is priceless, isn’t it?

1. Fartman

There was no way I couldn’t place this one right at the top of the list, especially given how many people saw it live and on TV and how infamous it became immediately. This is the sort of classic Howard stunt that, if there had been Twitter, Facebook, YouTube and a bigger Internet presence in general in 1992, would have gone viral a million times over. It went down at the 1992 MTV Music Awards, back when those actually meant something to people. Stern, who is well known for his love of, shall we say scatological humor, came down from the ceiling on wires wearing what appeared to be a crazy Elvis-inspired costume, labeled “Fartman.” I’m sure you can imagine what happened next. Yup, he pretended to unleash a big one, exposed his buttocks and was banned from the MTV show for life. There’s a surprise- Howard Stern made a fart joke and got in trouble; nobody saw that coming?

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