Freeloader's name was inspired by "Freddie Freeloader," one of the modal post-bop gems that jazz trumpeter Miles Davis wrote for his famous and highly influential Kind of Blue session of 1959. But Freeloader does not sound anything like any of Davis' groups; in fact, its music isn't jazz at all. Rather, the New York-based trio specializes in raw, gritty, earthy roots rock, and its main influences range from the Rolling Stones, Bob Dylan, and the Band to Gram Parsons and Tom Petty. Other valid comparisons include John Cougar Mellencamp and Steve Earle. Although Freeloader didn't come together until the late '90s, the threesome shows no awareness of contemporary alternative rock as most of its influences are Baby Boomer artists who emerged in the '60s or '70s. Freeloader has often been described as a northern band with a southern sound and its leader/founder, Scott Sinclair, is not a native New Yorker. Sinclair (who writes the trio's material) grew up in Texas, but he had moved to the Big Apple by the time he formed Freeloader in April 1999. Before Freeloader, Sinclair had only considered music a hobby; he had been earning his living as a financial analyst and had a master's degree in developmental economics. Playing and writing music was something Sinclair did on the side, but by early 1999, he had left the corporate world and was determined to be a full-time musician, even if it meant a loss of income. With Sinclair on lead vocals and guitar, Matt Dublin on bass and keyboards, and Ezra Oklan on drums and percussion, Freeloader's original lineup favored a power trio format. In 2000, Sinclair entered a Hoboken, NJ, studio with Dublin and Oklan and recorded Freeloader's debut album Custom/10. But not long after Freeloader recorded that CD, Dublin and Oklan left Sinclair's band. Keeping the power trio format, Sinclair hired bassist/singer Mason Pitts to replace Dublin and drummer Adam Chasan to fill Oklan's shoes. Pitts and Chasan had both been in various bands before Freeloader. Originally from the Deep South, Pitts had played bass with a Chapel Hill, NC, outfit called Knocked Down Smilin'; he moved to New York in 1997 to study music. Chasan, meanwhile, had been a member of the New York bands Supple and Poolsville. With the new Sinclair/Pitts/Chasan lineup in place, Freeloader started to develop a small following in New York and played a lot of gigs in the South (where its earnestness and down-home outlook went over well in some clubs). Sinclair put out Custom/10 independently in October 2001. Gigs with Cracker, Eve 6, and Hootie and the Blowfish's Mark Bryan gave them valuable road experience, and when they left the touring circuit they had made a few new acquaintances. Specifically, Cracker singer David Lowery, producer Brian Paulson, and producer Eric Ambel, who all agreed to produce the band's next set of sessions. They traveled to studios in New York City and Virginia that summer to lay down some tracks and prepare for a fall tour.
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