In 2014, Cumia was fired by SiriusXM Radio after posting a series of racist tweets in which he claimed to have been assaulted by a Black woman.

After his parents separated, Cumia spent his early teenage years living with his father in San Juan Capistrano, California.

[8] He wanted to get into radio, and was influenced by popular New York City personalities Howard Stern and Don Imus.

He and his brother Joe decided to enter the contest, and recorded an entry as Rotgut titled "Gonna Electric Shock OJ" to the tune of "(Sittin' On) The Dock of the Bay" by Otis Redding.

[independent source needed] Hughes and Cumia accepted an offer to host afternoons at WAAF in Boston, Massachusetts, and launched Opie and Anthony in March 1995.

[14] Cumia originally thought that by getting into radio he would make very good money, but later said his salary at WAAF was barely higher than doing manual labour.

In 2012, he launched Live from the Compound via Ustream which he started as a hobby and involved discussions on a variety of matters and "drunk karaoke".

In August 2015, Cumia relocated his show to a studio in New York City and hired far-right commentator Gavin McInnes.

[33] He posted tweets saying that Black people were "incapable or unwilling to assimilate to a civil western society", calling them "things", "monsters", and "animals".

[independent source needed] On March 31, 2021, Cumia launched a second show titled Compound Censored, which he co-hosts with Vice Media co-founder and comedic commentator Gavin McInnes.

[39] Along with Opie, Cumia co-hosted XFL Gameday, a pregame show for Vince McMahon's startup football league, for four weeks in February 2001.

"[40] Opie, along with Anthony released a compilation of segments from their show that aired on WAAF on a CD entitled Demented World in November 1997.

[41][independent source needed] The Traveling Virus was a comedy tour headlined by Opie and Anthony, as well as friends of the show, that performed in various cities during 2006, 2007, and 2008.

[independent source needed] On the morning of March 26, 2008, Opie & Anthony revealed they had taped a pilot for Comedy Central.

The show was titled Search & Destroy and it featured teams of comedians performing various tasks throughout New York City.

[49] He was arrested by Nassau County police on charges of strangulation, assault, criminal mischief, and unlawful imprisonment.

[50] In June 2016 Cumia pled guilty to third-degree assault and criminal obstruction of breathing in a plea deal.

[51][independent source needed] Cumia spent April 2016 in a rehabilitation facility in the Tampa Bay area in Florida.