He went to college to study English in Chapel Hill, North Carolina, but dropped out and relocated to New York City, where he began his music career as a subway busker.

In reviewing the album, Laurel Bowman of Alternative Press wrote that Block "practices the alchemy of melodious discord: pretty enough to draw you in, rough enough to keep you listening.

[7] The positive reception for Penn Station helped Block book tours opening for The Brian Setzer Orchestra, Bob Mould, and They Might Be Giants, garnering notice from producer Glen Ballard.

In 1998, Ballard, (known for co-writing and producing Alanis Morissette's album Jagged Little Pill) started the Capitol Records imprint Java, and chose Block to be the first signed artist.

In a positive review, critic Nick DeRiso stated that songs on the album "blend the brutal, hard-won spoken-word honesty of Lou Reed with a rootsy, rattling cadence" and said that Block is a "vocalist capable of subtle, deeply emotional complexity.

"[17] Journalist Steven P. Marsh noted the personal nature of the songwriting, stating that the songs on the album "are perfectly crafted stories of a man whose life has had some twists and turns.

[19] In "Abby Singer/Songwriter," Jamie Block plays himself, as a divorced stockbroker has-been who was once an indie-rock star signed to Capitol Records who meets Onur Tukel, a hapless middle-aged filmmaker who has just moved to Brooklyn.

In this coming-of-middle-age story, Onur persuades Block to sink his money into a series of increasingly absurd music videos to promote his comeback as a musician.