Benjamin was born on May 23, 1966, to a Jewish family in Worcester, Massachusetts and graduated from Worcester Academy in 1984 and Connecticut College in 1988.

He was the guest on Space Ghost Coast to Coast in its eighty-first episode, “King Dead” on December 17, 1999 where Zorak and Moltar kidnapped him. He has appeared in the television show Cheap Seats, on ESPN Classic, as “Gene Stapleton” and “Rabbi Marc Shalowitz”. He co-starred in Todd Barry’s short film Borrowing Saffron, and portrayed a talking can of vegetables with a shameful habit of autofellatio in the film Wet Hot American Summer. He made short cameos in Not Another Teen Movie as the football trainer, and on the FX Network comedy-drama Rescue Me as the pimp “F-bomb” in season two. He can be seen in Turbocharge-the Unauthorized Story of the Cars, a comedy biopic about ’80s rock band The Cars, playing the role of Cars’ manager Elliot Roberts in his usual deadpan comedic delivery.

In 2009, Benjamin and David Cross created and wrote for Paid Programming, a live-action pilot for Cartoon Network’s late night programing block, Adult Swim. Paid Programming was not picked up for a full series, and Benjamin referred to it as an “abject failure”.

Benjamin starred in the Comedy Central series Jon Benjamin Has a Van, which he co-created with comedian Leo Allen. The series debuted on May 14, 2011; a total of 10 episodes aired, the last on August 10, 2011.

Beginning in 2013, Benjamin’s voice can be heard as the narrator of a series of TV commercials for Coke Zero, including some with tie-ins to ESPN’s College Game Day program.

In 2014 Benjamin was named as the year’s best male comedy performer for his work on Bob’s Burgers and Archer by the Vulture TV Awards, a digital expansion of New York magazine.

In 2015, despite not knowing how to play any instrument, Benjamin released his first jazz album, Well, I Should Have…. Benjamin “played” piano and was joined by Scott Kreitzer on sax, David Finck on bass, and Jonathan Preitz on drums.

Benjamin wrote the comedic autobiography Failure is an Option: An Attempted Memoir, which was published by Penguin Random House in May 2018. He narrated the audiobook.

Benjamin began appearing in commercials for Arby’s restaurant chain in 2018 as their new spokesman promoting their variety of meats “for sandwiches”.

On January 22, 2020, Benjamin endorsed Bernie Sanders for president and narrated a series of videos on Sanders’s health care proposals.

In March 2020, Benjamin was the voice of Saddam Hussein in Blowback, a podcast of the Iraq War created and hosted by Brendan James and Noah Kulwin.

In September 2020, Benjamin narrated the launch video for the Gravel Institute.