[5] After graduating from college, Hughes landed a job in the promotions department at WCMF in Rochester, New York, but soon moved to work on the station's morning show then hosted by Brother Wease.
[5] Hughes's next job was at WBAB on Long Island as the host of The Nighttime Attitude, a rock music show from 8:00 p.m. to midnight.
One of the participants was from a local band named Rotgut that featured Anthony Cumia as lead singer with his brother Joe on guitar.
After Hughes produced an air check and had sent it to several radio stations, he and Cumia accepted an offer from WAAF in Boston to host afternoons.
Opie and Anthony told their listeners that Menino had been killed in a collision with a semi-trailer truck on interstate 95 while traveling with a young female Haitian prostitute in Jacksonville, Florida.
[13] In 1999, Hughes considered leaving the show; however Anthony convinced him to stay, and bring Jim Norton on full-time as a go-between for their off air troubles.
[16] On May 15, 2007, XM suspended Opie and Anthony for 30 days, in response to a broadcast featuring a homeless man brought into the studio.
Opie and Anthony dubbed the man, who mentioned the possibility of raping Condoleezza Rice and Laura Bush, "Homeless Charlie".
On July 3, 2014, Cumia was fired by SiriusXM, after making a series of tweets following an alleged off-air incident with a black woman on the street.
Cumia gave his blessing for the Sirius XM show to continue without him, acknowledging Hughes and Norton's obligation to fulfill their contract with SiriusXM.
[20] In October 2014, Hughes and Norton signed a new contract to continue the SiriusXM show,[21] and the channel was re-branded to Opie Radio which was kept until January 2017.
[28][29][24] On March 19, 2018, Hughes said that he had signed a contract with Westwood One to develop a podcast and a traditionally syndicated radio show for the network.
[33] In February 2001, Hughes and Cumia hosted XFL Gameday, a half-hour pre-game show for Vince McMahon's startup football league that aired nationally on Saturday nights on select NBC affiliates prior to the evening's games.
The pair were almost banned from Giants Stadium for life during the filming of one episode when they imitated a proposed XFL rule where first possession was determined by placing the ball at midfield and having two opposing team-members attempt to get it.
The pair released a compilation of segments from their show that aired on WAAF on a CD entitled Demented World in November 1997.
The show was titled Search & Destroy and features teams of comedians performing various tasks throughout New York City.
[40] On March 16, 2010, the lawsuit was dismissed as the judge ruled that the original news story was newsworthy, noting that all parties had agreed that no sex tape actually existed.