Chisel's eventual breakup in 1997 came after their critically acclaimed sophomore full-length, Set You Free. The band's reputation seemed to flourish after their breakup, however, and even though the retro trends in indie rock would eventually gain enough popularity to inspire the likes of mod underground sweethearts like the Mooney Suzuki and the Delta 72, the influence of Chisel goes largely unnoticed. Leo went on to a variety of musical endeavors, including two years of on-again, off-again touring as a guitarist with the Spinanes, and a short-lived project called the Sin Eaters that he founded with his brother, Danny Leo, on drums and former Van Pelt bassist Sean Greene. The Sin Eaters' progressive, politically charged, punk-fused rock and local all-star lineup took the New York underground by storm between 1997 and 1998, until Danny Leo left the band to work on his own material and eventually founded the Holy Childhood.
When the Sin Eaters disbanded without a recorded legacy in 1998, Ted Leo was left without a band and began his career as a solo artist. He remained active by wearing the hat of producer for the Secret Stars' debut record, Geneologies, and touring alone on the East Coast and through the Midwest. He eventually recorded a self-titled full-length on his homestead, Gern Blandsten Records, in 1999 with a new band, the Pharmacists, that included various friends and affiliates of the Secret Stars, including Jodi Buonanno. This record marked a notable change in Leo's sound, which, mostly due to his performance practices, was more and more rooted in songwriting legends like Billy Bragg and Alex Chilton. Ted Leo & the Pharmacists released a split with the One AM Radio later that year as a collaborative effort of both Gern Blansten and Garbage Czar.
In the spring of 2000, Leo's sophomore effort, Treble in Trouble, was released on New Jersey-based Ace Fu Records, displaying a more aggressive and romantic bent to Leo's writing. In the early summer of 2001, Leo released a polished studio effort, The Tyranny of Distance, on Lookout Records. A strong contender for record of the year, it was followed by the equally strong Hearts of Oak in 2003. Shake the Sheets. which appeared in 2004, would prove to be his last for then-troubled Lookout, as Leo signed with Chicago-based indie Touch and Go in February 2006. A tour followed in March, on which he was supported by the Duke Spirit and Les Aus. He continued touring throughout 2006, festivals such as Coachella and headlining dates alike, as new material was worked on as well. Ted Leo & the Pharmacists eventually returned in March 2007 with full-length number five, Living with the Living. In 2009 Leo signed with Matador, and the following year he released his first record with them, The Brutalist Bricks. ~ Nate Cavalieri, Rovi