Howard Stern's 10 most outrageous moments

Howard Stern is a legendary radio personality, but he attained that status in part through his willingness to do outlandish, wacky things with his guests. Sometimes things went off the rails, but whether everything went as planned or not, the moments themselves only contributed to Stern's legacy.

Everyone loves Jerry Seinfeld, right? Not Stern or frequent guest Gilbert Gottfried. They unleashed dueling Seinfeld impressions, took a nasty call from a woman who dated Jerry, then left a 28-minute message on the comedian's voicemail.

Stern's absurdist editing of excerpts from the ex-governor's memoir alienated hockey moms. What's the difference between a pit bull and Howard Stern? Twenty million listeners.

In one instance, Howard went against his tendency to overly sexualize women: He tried to talk a ''boob-job contest'' winner out of claiming her loot. Charmed by her girl-next-door personality, Howard begged Erica the Gymnast not to get breast implants. Ultimately, he did help fund her surgery, but only on the condition that she ''wouldn't go too big.''

If there's an organization that's the opposite of Mensa, Stern regulars Beetlejuice and Gary the Conquerer should be the founding members. Howard decided to pit them against each other in an epic battle of wits with IQ-rattling questions like ''How do you spell 'red'?'' Needless to say, they made any one of Jay Leno's uninformed pedestrians on ''Jaywalking'' seem like Neil deGrasse Tyson by comparison.

A true rite of passage for Howard's more broad-minded female guests is a spin on the Sybian. This being a family site, we can't tell you what exactly it does. But there's a reason adult film stars like Jenna Jameson are usually the only takers. Howard's biggest coup ever? When Carmen Electra volunteered to get in the saddle.

When Stern learned that executive producer Gary Dell'Abate had taped an embarrassing apology to his ex-girlfriend begging her to take him back, it was only a matter of time before it hit the air. A charity fund was even established to get his permission. The final tally? $18,000. Dell'Abate's humiliation? Priceless.

In 2001, recently fired New York Daily News gossip columnist A.J. Benza — who frequently appeared on air with the Stern crew — was mocked for his dismissal by sidekick ''Stuttering'' John Melendez. Benza promptly slapped him across the face...which got him exiled from Stern's show. Melendez, however, was so humiliated all he could do in his shame was take a job as Jay Leno's Tonight Show announcer.

In 1998, Howard invited Melissa Rivers and her fiancé John Endicott on his program. His wedding gift? As much money as she could grab from a box with air vents that can blow cash around. Rivers refused to demean herself...so she had her assistant Dorothy do it instead. Klassy!

Troubled Stern sidekick Artie Lange lunged at his personal assistant Teddy while on the air, then walked off the show. Lange's stated reason for the altercation? Teddy had embarrassed him by calling Bloomingdale's ''Bloomie's.'' Money issues were the real reason, and Lange returned later in the broadcast to apologize and tender his resignation. Less than two weeks later, though, he was back, though Sirius Radio announced that another such incident would cost him his job.

The greatest Howard Stern moment of all time didn't even come from Stern himself, but it showed the extent of his reach. During O.J. Simpson's infamous slow-speed chase on June 17, 1994, a prank caller with an odd patois punk'd a stone-faced Peter Jennings with an on-the-scene account of O.J. inside his white Ford Bronco. When the caller finally telegraphed it was a stunt using Stern's catchphrase, it was the ''Baba Booey'' heard 'round the world.