Bailey joined May Weather in March of 2009 in his senior year of high school. May Weather hails from western Maryland. Since 2008, they have been quickly gaining a respectable following and presence in the music scene. With two album releases, hundreds of shows under their belts across eleven states, and endless determination, the band shows no sign of slowing down. The influence of ska, rock, jazz, metal, and everything in between is very evident in their unique style of music. May Weather has played with nearly 1000 different bands most notably Big D and the Kids Table, Ballyhoo, The Pietasters, The Slackers, The Snails, Survey Says!, The Toasters, Spoken, and I, The Breather. Both of the bands albums “This is Almost and Album” and “Your Life on Optimism” have received countless praise from music critics and professional musicians alike. Most notable praise has come from music promoter, reviewer, and blogger, Ska Lives (a division of Indie Vision Music) as well as Leanor Till (Jeff the Gurl) from Five Iron Frenzy, Karen Roberts (former lead singer of Chase Long Beach), and Matthew Stewart of Streetlight Manifesto who wrote, “I loved the EP. Ska is still alive, and it lives in Maryland.” May Weather’s live show has been praised as one that is unique, highly energetic, and fun for people of all ages.