He is also best known for his October 16, 2014 stand-up routine, which brought the sexual assault allegations against Bill Cosby to public attention and outcry, for which he was lauded.

[12] He left after six months,[4] although he continued to portray various characters on the show for 9 episodes from 2010 to 2012 such as "Gus", "Homeless Guy" and "Bum".

[4] He used to host a weekly stand-up comedy show at The Knitting Factory on Sunday evenings in Brooklyn, New York.

[22] On April 30, 2020, he released a single called Judge Judy, paying homage to the series of the same name after it was announced that the show would end in 2021.

[23] On October 16, 2014, at the Philadelphia club The Trocadero, Buress was recorded doing an extended routine about sexual assault allegations against comedian Bill Cosby.

[24] Buress addressed Cosby's legacy of "talk[ing] down" to young black men about their style of dress and lifestyle.

Buress criticized the actor's public moralizing by saying, "Yeah, but you raped women, Bill Cosby, so that kind of brings you down a couple notches."

[25] Buress had been doing the same Cosby routine for the previous six months with little response,[26] but the October performance went viral after being posted on the website of Philadelphia magazine.

[34] After living in New York City, he moved back to his hometown of Chicago in 2017 and settled in its Wicker Park neighborhood.

[36] The arrest report revealed that Buress was detained because he approached the police officers and would not stop asking them to call an Uber for him.

The Miami New Times reported that the arresting officer has an alleged history of violence and was previously disciplined by internal affairs for an alcohol-fueled assault.

[39][40] In July 2020, Buress brought a lawsuit against the City of Miami and the officers involved for constitutional violations in connection with the incident.

[42] Buress owns a building in Chicago;[43] in 2017, he removed residential tenants in order to convert the property into Airbnb short-term rental units.