Anthony was born on August 26, 1967, and raised in Marin County, California. He attended Marin Catholic High School. He is open about his childhood and has discussed growing up with a neglectful and alcoholic father, as well as an emotionally unavailable mother who was raised by alcoholics. He cites his neglected childhood as the source of his mental health and anger problems, and based his 2015 comedy tour and subsequent album Hot Head around this topic.

Anthony was also the creator, producer, and editor of Walking the Room, a podcast that he co-hosted with comedian Greg Behrendt from 2010 to 2014. They hosted a show together on the Comedy World Radio Network in 2001 and collaborated again on The Greg Behrendt Show in 2006–2007. Anthony regularly appears as a guest on various other podcasts, including FOFOP where he has been given the endearing name of “Guest Charlie Number One”.

Anthony has written extensively for different mediums. He was a contributing writer for SuicideGirls and the Comedy Film Nerds websites, and had a blog called Stop All Monsters. Anthony is also a television writer. He has written on AMC’s Talking Dead, Between Two Ferns with Zach Galifianakis, Pretend Time, and The Greg Behrendt Show He wrote on Maron for three seasons. He also directed one episode, as well as appearing as an recurring actor. He was nominated for a WGA Award in 2015 for a Maron episode he wrote titled “Racegate.”

Anthony has performed stand-up all over the world, including the Melbourne International Comedy Festival in 2015, where the Herald Sun gave his show Hot Head a 4 star review and called it “Hugely Enjoyable.” In 2015, he also appeared on the nationally televised Cracker Night as part of Sydney Comedy Festival 2015. He has released two comedy albums, Hot Head and Shame Chamber. He frequently performs around Southern California.

On July 9, 2015, the history website and podcast Damn Interesting posted an open letter titled “A Special Note to the Writers at The Dollop”, accusing Anthony of plagiarizing Damn Interesting’s original content for use on The Dollop. The post included a 2,670-word example of text Anthony plagiarized primarily from Damn Interesting, with smaller portions taken from KnowledgeNuts and Slate. In response to these allegations, Anthony stated on Reddit that “historical facts are not copyrightable”.

Anthony is best known in recent years for the comedy podcast The Dollop, which he co-hosts with comedian Gareth Reynolds; the podcast sees Anthony presenting a notable event or person from American history to Reynolds, who usually has no knowledge of it. The podcast is on the All Things Comedy Network. The two wrote a book based on the podcast titled The United States of Absurdity: Untold Stories from American History, which was released in 2017.

Since 2019 he has co-hosted the podcast The West Wing Thing with Josh Olson.

On August 25, 2019, author Josh Levin posted a thread to Twitter accusing Anthony of plagiarizing one of Levin’s articles for a Dollop live show at Chicago’s Athenaeum Theatre in 2017. The thread included screenshots of Dollop transcripts beside his own text, showing several nearly identical passages. In a reply to the thread, author Paul Brown stated that The Dollop had also plagiarized sections of his own book The Rocketbelt Caper for a 2017 episode.