Full disclosure: I have worked for Infinity Broadcasting, CBS Radio, WXRK-FM, Westwood One, Clear Channel, and SiriusXM.
It's been quite a week for Howard Stern and his one-time arch rival Gregg "Opie" Hughes. Stern began the week railing at HBO and the Rock and Roll Hall of Fame for editing his speech inducting Bon Jovi, while Opie launched his long awaited podcast, the first digital content from radio syndication giant Westwood One. If that all sounds like a 1999 reunion party gone wrong, perhaps that's the real problem here: that radio has grown stagnant, and its giants have to a certain degree been passed over.
The Howard Stern Show and Opie and Anthony defined radio in New York and beyond in the late 1990s and early 2000s. Stern had been a major name in the city since 1982, when he arrived and made a splash at WNBC. His real break, however, came when NBC fired him in 1986. He was quickly picked up by Infinity Broadcasting's WXRK-FM. "K-Rock" recognized Stern's talent for making great radio and attracting publicity, and worked with him to syndicate The Howard Stern Show across the nation. By the 1990s, Stern was nabbing new markets constantly, becoming perhaps the first modern superstar in the history of radio, and expanding his empire with books, a televised simulcast on the E! Network, and a major motion picture.
One of Stern's many strengths has always been a brutal competitive instinct. That's why, when Opie came to New York with his on-air partner Anthony Cumia, sparks were destined to fly. In 1998, four years after the duo debuted their show on Long Island's WBAB, they returned to New York - the number one market in radio - as the afternoon drive hosts at K-Rock's sister station, WNEW-FM. Opie and Anthony were unabashed fans of the Stern Show (Cumia made an early appearance on Stern's E! show, impersonating former head writer Jackie Martling), but the admiration was not mutual.
Opie and Anthony took the antics that propelled Stern to fame and infamy in the '80s and '90s and dialed it up a notch. Like Stern, they came to Infinity riding the crest of a high-profile firing. They were exiled from Boston's WAAF for announcing (falsely) that Mayor Thomas Menino died in a car accident on April Fool's Day, 1998. They brought this rebellious energy to New York, with high-profile stunts like 1999's Homeless Shopping Spree. As their success grew, they worked with Infinity and rival network Greater Network to syndicate the show, ultimately expanding into nine markets. Stern - who as seen in the video above, had O&A branded as rip-offs before he ever heard them - was not impressed. An internecine war began between the two shows, with K-Rock's program director Steve Kingston allegedly threatening artists that he would pull their music from the station if they appeared on Opie and Anthony. O&A retaliated by revealing an upcoming Stone Temple Pilots concert that was going to be announced the next day exclusively on the Stern Show.
Stern's response was to demand a gag order. Infinity management forbade Opie and Anthony from ever discussing Stern, and allegedly added a stipulation to their contracts that would fine them $100,000 for any mention of him. The two shows, by this time mortal enemies, continued to follow a very similar trajectory over the next several years. Opie and Anthony were ultimately fired in 2002, although Infinity paid them and forced them to adhere to the terms of their deal, meaning they couldn't return to radio until 2004. By that time, satellite radio had debuted, promising a safe haven for talented broadcasters to throw off the yokes of censorship, while also getting national exposure. When O&A signed their next deal in August 2004, it was with XM Satellite Radio. Their signing legitimized satellite radio and helped pave the way for a future, fateful merger with rival Sirius Satellite Radio.
While Opie and Anthony labored in lucrative but maddening silence, Stern felt the heat turned up to levels unprecedented in his decades-long career. As America faced a new century fraught with terror and war, the culture under president George W. Bush embraced a strange and selective form of puritanism. The culture wars accelerated after the infamous 2004 Super Bowl performance by Justin Timberlake and Janet Jackson. The ridiculous incident, which came to be referred to as "Nipplegate," energized an already fine-happy FCC, and they went after Stern like he was Lenny Bruce on steroids. Feeling the heat from the government and losing support from a panicked Infinity, Stern dialed down his show's content, losing much of the ground that he had conquered and that was now being exploited by less high profile broadcasters in the safe harbor of obscurity and small markets. Affiliate stations began dropping the Stern Show, while at the stations where the show continued to air, program directors began abusing the dump button in the hopes of avoiding further bad press and government-imposed fines. It wasn't fun or funny for Stern or his listeners. In 2006, seeking to restore the creative freedom that he'd fought so hard for, Stern parted ways with K-Rock and Infinity, and The Howard Stern Show moved to Sirius Satellite Radio.