Opie and Anthony celebrate twenty years in radio with a live SiriusXM Unmasked from Carolines in NYC

On Thursday night at Carolines in New York City, legendary radio hosts Opie & Anthony sat down with Ron Bennington (of the Ron & Fez Show) to talk about their 20 year career in radio. A career that took them from Long Island to Boston and back to NYC. A career that, on more than a few occasions kicked them around and set them up for moments when they were forced to make career-defining decisions.

Bennington hosted O&A as part of SiriusXM’s interview series Unmasked. Where Bennington takes an in-depth look at the career of an artist. However, this Unmasked was different as O&A were on hand to celebrate 20 years of highs and lows of their career in broadcasting. And in a packed comedy club in front of diehard fans is where the duo broke down their story to Bennington. Here’s what we learned from the hour long conversation with the boys.

Anthony’s Brother was responsible for O&A’s partnership
It was a chance meeting and a spark was formed. Opie had been doing the night shift on a show, “The Nighttime Attitude” at WBAB in Long Island. It was Anthony’s persistent brother (Brother Joe) who managed to get a tape of his band Rotgut and their parody songs to Opie to play on the air. The Rotgut parody songs exploded in popularity and Opie soon had Rotgut in studio. Rotgut’s frontman happened to be Anthony, and the proverbial spark happened. Anthony even joked that Brother Joe probably thought he was going to be the third member of their team. However, it took a determined Opie to convince the program director that Anthony was the right man for the job because, “nobody else at the station at the time got it.”

Anthony came at it from a different perspective
“I’ll get to do radio and within a month make millions!” is what Anthony thought, not knowing how the life of a DJ isn’t all it appears to be financially. He quickly came to this realization when he visited Opie at his house and it wasn’t glamorous.

Anthony soon learned why Opie would complain about his bosses and that their nighttime bits were beginning to gain traction while being played by the WBAB morning show. In fact, during the day Anthony would be at his day job installing HVAC ductwork (aka a “tin knocker”) in 130 degree attics and hear himself on the radio from these morning clips and not be able to understand why he wasn’t making $$.

They had to make the move from WBAB to WAAF in Boston
When they realized they had to move to a different market in order to advance their career O&A sent tapes out to other stations. They were offered jobs in two markets and decided on WAAF in Boston. When it came time to pack their very cramped U-Haul with their belongings there wasn’t a lot of room for Opie’s stuff when Anthony pulled up to his place to get him. Rather than storing his stuff or shipping it to Boston, Opie decided to smash what he wasn’t bringing right there on his front lawn. Acting as a bit of a cathartic moment and solidifying for them that it was a “can’t fail” move for them. Anthony threw his “tin knocking” sheet metal tools out the window of their car on the side of I-95 as they made the drive north. It was do or die.

They became a massive hit in Boston, but were making no money
O&A were an instant hit in Boston and slowly started taking their share of the Boston on WAAF. They were “killing it and making no money.” After a fruitless salary negotiation at a Chinese buffet that involved comically passing figures back and forth via a note like in the movies, O&A realized it was time to move on from Boston. They tried to purposely get fired and did it with dramatic fashion with the now infamous April Fools story about reporting on the Mayor of Boston’s death.

Their story is full of gut check moments
Every major step of O&A’s journey came from those moments of “What are we doing? Who are we listening to?” Whether it be a conscious decision to leave WAAF, their decision to do it their own way at WNEW, to calming down the carnival on SiriusXM. O&A often had gut check moments that led to better opportunities.

WNEW was the “Golden Age” of their show
The duo described to Ron Bennington that once they made the conscious decision to do things their own way at WNEW early during their tenure there, they started to dominate. WNEW was a runaway train and as Bennington put it, “the show that never ended.” Until it did…

We all know of O&A’s now infamous firing from WNEW after the “Sex For Sam” promotion, urging couples to have sex in various locations across the city to gain points and Samuel Adams. On the third annual celebration of the promotion, spotter/comedian Paul Mercurio was with a couple at St. Patrick’s Cathedral who performed acts. Guards were argues with and cops came. The Catholic League called for O&A’s jobs and threatened to have the station’s license revoked. O&A and Bennington stated after that incident, it seemed radio stations across the country put the clamp down on their jocks.

The duo were indefinitely suspended and literally paid for the remainder of their contracts by Infinity Broadcasting (WNEW’s parent company) to keep them from getting jobs with Clear Channel, Infinity’s competitor which would’ve put them up against Howard Stern in the mornings.