Career
Shaffir's first and only comedy performance on stage before he moved to Los Angeles took place in his early twenties at an open mic night at a "sports comedy place in Northern Virginia". Following his graduation from university, Shaffir moved to Los Angeles to improve his chances of success as a stand-up comedian. He took up work answering the phones at The Comedy Store, which led to positions in the cover booth and "the door", until owner Mitzi Shore made him a paid regular four and a half years later. His early influences in comedy include watching showcase comedy shows on television and comedians on The Tonight Show with Johnny Carson. He cites Bill Burr as his favorite living comedian.
Shaffir first became known to a wider audience with the viral video series The Amazing Racist. He became an opening act for Joe Rogan in the late 2000s and began touring with Rogan and fellow comics Joey Diaz, Duncan Trussell, Tom Segura, Brian Redban, and Eddie Bravo. In 2009 he appeared at the Montreal Comedy Festival as part of The Nasty Show. The following year he created, produced and hosted the monthly live show This Is Not Happening, with Eric Abrams, a stand-up comedy featuring numerous comedians telling true-life stories around a theme. The show would become a regular feature at comedy festivals and debuted as a web series in 2013 and premiered in January 2015 on Comedy Central. He left the show as producer and host in 2017 after selling his third special, Double Negative, to Netflix rather than Comedy Central. Roy Wood Jr. replaced him as host.
In 2010 Shaffir appeared on the 3rd episode of the Joe Rogan Experience, his first of 59 appearances on the show. In 2011, Shaffir began his podcast, Skeptic Tank. On most episodes, Shaffir picks a subject his guests (mostly comedians) can discuss as experts. While subjects are often comic he's also discussed serious issues such as mental health, suicide, rape, and prison. Every 50 episodes the comedy team Danish and O'Neill appear as guests. In 2013, Shaffir began to cohost the sports podcast Punch Drunk Sports with fellow comedians Sam Tripoli and Jayson Thibault.
Shaffir spent several years earning a living as a commercial actor, appearing in ads for Coke Zero, Subway, Domino's, and Bud Light. He appeared in the comedy feature film Keeping Up with the Joneses (2016). As of 2017, Shaffir claimed to have no interest in pursuing acting as it could take him away from his stand-up.
Following the death of basketball player Kobe Bryant in 2020, Shaffir caused controversy with a video posted to Twitter in which he stated: "Kobe Bryant died 23 years too late today. He got away with rape because all the Hollywood liberals who attack comedy enjoy rooting for the Lakers more than they dislike rape. Big ups to the hero who forgot to gas up his chopper. I hate the Lakers. What a great day." A New York comedy club where Shaffir was scheduled to perform canceled his performance after it received phone threats.
