The Caribbean operate primarily out of plush Washington, DC, but also maintain satellite stations in Baltimore, Maryland and the Gulf Coast of Florida. The group came to exist when Tony Dennison, who was playing drums for Smart Went Crazy (Dischord Records' quietest band), went to see the group Townies play at DC's 930 Club with Low and Pell Mell in 1995 on a hunch.
The hunch -- whatever it was -- paid off. Mutual admirations were formed and the two groups toured together through the Southern U.S. in 1996. Smart Went Crazy had just recorded the superb Now We're Even (Dischord) while Townies had slightly earlier made the slowburn beauty, The Apologetic Sound (Little Voice) and would soon record the double EP Pluperfect/Brotherhood of Sleeping Car Porters (Little Voice).
By 1999, both groups had split, but friendships forged on tour remained. Matthew Byars and Michael Kentoff, fresh from the dissolution of Townies, contacted Dennison to gauge his interest in assembling a recording-only group. Dennison was way into it. This new assemblage, the Caribbean, eschewed normal recording studios with expensive hourly rates, pesky clocks, and "qualified" engineers and quietly recorded a debut EP on its own called The Caribbean, which came out in 2000 and contained music by the trio and several instrument-playing friends.
Shortly thereafter, the group signed to Canadian pop label, Endearing, and released their first full-length, Verse By Verse to international acclaim in 2001. Realizing that it missed performing live, the trio added Don Campbell as a do-everything type to play mostly keyboards and bass in the touring quartet. Campbell would not be shaken and soon joined the Caribbean on a full-time basis. Dennison recorded all of his drum parts for the next record over a three-week span in the Summer of 2001 and shipped out of DC to pursue graduate school in Florida. The group completed recording History's First Know-It-All in the Fall of 2002 and the new record came out on Endearing and, in Europe and Japan, the visionary Tomlab label in the Spring 2003.