One of the most acclaimed and well-known musicians associated with New York City's anti-folk scene, Jeffrey Lewis has been active in music since the late '90s, writing sharp, literate, and sometimes hilarious songs about city life, everyday occurrences, history, and underground culture. Typically delivered in his signature deadpan vocal style, his songs frequently namecheck influences such as the Fall, the Misfits, and Will Oldham, and often have a rambling, shaggy-dog narrative or a punch line. On occasion, he's written songs detailing the entire history of certain bands or music scenes, as on his 2004 single "The History of Punk on the Lower East Side of NYC 1950-1975," and a series of songs he wrote about historical events (including the Cuban Missile Crisis and the French Revolution) was featured on the History Channel's website. In addition to his music, Lewis is a renowned illustrator and writer; he's written and drawn numerous graphic novels, had his work published in The New York Times, and designed cover art for bands such as the Moldy Peaches.

Jeffrey Lewis was born in New York City in November of 1975. Lewis' beatnik parents didn't have a television in the home, so comic books and his father's blues records were early obsessions. Although the first album he bought was Whodini's Escape, high school brought an interest in the Grateful Dead (he went to 40 shows) and Nirvana. After graduating from New York State University at Purchase (his senior thesis was on Alan Moore's graphic novel Watchmen), Lewis started making music on a guitar on loan from his father and was turned on to the more oddball sounds of the Fugs, David Peel the Lower East Side, and the Godz.

In 1998, he could be found playing open mikes and releasing Indie-Rock Fortune Cookie, a cassette packaged with one of Lewis' comic books. A CD-R compiled from the cassette landed in the hands of Rough Trade, courtesy of the recently signed Moldy Peaches, and the label issued The Last Time I Did Acid I Went Insane and Other Favorites in 2002. An appearance on the Moldy Peaches-compiled Antifolk, Vol. 1 followed, and a second album, It's the Ones Who've Cracked That the Light Shines Through, appeared in 2003. Lewis toured Europe with members of the Moldy Peaches in support of 4 Seasons, a box set featuring a comic book, a DVD, and two 7" singles.

The 2006 album City Eastern Songs was credited to Jeffrey and his brother Jack, while 2007's 12 Crass Songs featured a dozen songs originally written and performed by the British anarchist punk band Crass. In 2009, one of Lewis' illustrations was etched into the B-side of Cornershop's comeback single "The Roll Off Characteristics (Of History in the Making)." That same year, his 'Em Are I arrived, featuring the single "To Be Objectified." Members of Dr. Dog, the Vaselines, and Au Revoir Simone appeared on his 2011 release A Turn in the Dream-Songs. Also in 2011, Lewis collaborated with Peter Stampfel of Holy Modal Rounders, releasing Come on Board that year, followed by Hey Hey It's...The Jeffrey Lewis Peter Stampfel Band in 2013.

He formed a band called Jeffrey Lewis the Rain and recorded "WWPRD," a song about Russian anarchist punk group Pussy Riot, which accompanied a comic strip of the same name that was published in London newspaper The Guardian. Lewis assembled a new band called Jeffrey Lewis the Jrams, who recorded an album in a single day in early 2014; the album included a spoken recital of "WWPRD," recorded live the previous year. Lewis returned to Rough Trade in 2015 for his next album, Manhattan, which was credited to Jeffrey Lewis Los Bolts. In 2018, Lewis released Works by Tuli Kupferberg, credited to Jeffrey Lewis the Deposit Returners, an ad hoc group including Peter Stampfel and Steve Espinola. The album featured interpretations of 15 songs by Kupferberg, a poet and activist who was one of the founding members of the Fugs; Lewis once collaborated with Tuli, illustrating an autobiographical piece for the collection The Beats: A Graphic History. Bad Wiring, a more existentialist outing billed to Jeffrey Lewis the Voltage, appeared in 2020. ~ David Jeffries & Paul Simpson, Rovi