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Stand-up comedy

Cosby lined up stand-up jobs at clubs in Philadelphia and then in New York City, where he appeared at The Gaslight Cafe beginning in 1961. He booked dates in cities such as Chicago, Las Vegas, San Francisco, and Washington, D.C. In the summer of 1963, he received national exposure on NBC 's The Tonight Show. This led to a recording contract with Warner Bros. Records which, in 1964, released his debut LP, Bill Cosby Is a Very Funny Fellow...Right!, the first of a series of comedy albums. His album To Russell, My Brother, Whom I Slept With was number one on Spin magazine 's list of "The 40 Greatest Comedy Albums of All Time", calling it "stand-up comedy's masterpiece".

Cosby's comedy genres included observational comedy, satire, surreal humor and deadpan. While many comics of the time were using the growing freedom of that decade to explore controversial and sometimes risqué material, Cosby was making his reputation with humorous recollections of his childhood. Many Americans wondered about the absence of race as a topic in Cosby's stories. As Cosby's success grew, he had to defend his choice of material regularly; as he argued, "A white person listens to my act and he laughs and he thinks, 'Yeah, that's the way I see it too.' Okay. He's white. I'm Negro. And we both see things the same way. That must mean that we are alike. Right? So I figure this way I'm doing as much for good race relations as the next guy."

In 1983, Cosby released the live comedy performance film Bill Cosby: Himself, in which he gave his views ranging from marriage to parenthood. The film also showcased Cosby's conversational style of stand-up comedy; for most of the performance, Cosby was seated center-stage, only getting up to emphasize a joke. Nearly all of Cosby's routine in the film concerned the trials and tribulations of parenting, frequently illustrated with anecdotes involving his own family. Many of the comedic routines presented in the film were precursors to Cosby's most popular sitcom, The Cosby Show. The film was well regarded by comedians and critics, with some calling it "the greatest stand up concert movie ever." Rolling Stone placed Cosby's concert film Bill Cosby: Himself as number 8 on its list of "The 25 Best Stand-Up Specials of All Time", acknowledging the significance of the film while still saying: "Yes, it's damned near impossible to watch anything the tainted comedian has done and not think of the headlines, the heckling, the revelations and what is, by any definition, monstrous behavior." They also placed Cosby at number 8 on their list of "The Best Stand-up Comics of All Time", saying: "Bill Cosby is not likely to perform again; listening to his records will never have that gentle, sweet sense of nostalgia for anyone; and while it is impossible to disconnect the performer from the man, scrubbing his name from the annals of stand-up would be impossible."

Cosby performed his first TV stand-up special in 30 years, Bill Cosby: Far from Finished, on Comedy Central on November 23, 2013. His last show of the "Far from Finished" tour was performed at the Cobb Energy Performing Arts Centre in Atlanta, Georgia on May 2, 2015. In 2014, Cosby was set to release his new standup special Bill Cosby 77 on Netflix. The release of the film was canceled due to allegations of sexual assault against Cosby. His last known standup performance prior to his conviction was held at the LaRose Jazz Club in Philadelphia on January 23, 2018.