Vocalist, songwriter, and guitarist Aaron Perrino met drummer Shawn Sears in a music theory class at Oneonta State University in New York, and Sears ended up managing Perrino's band the Waverlys. Bass player Jim Gilbert was also a student at Oneonta. The trio three ended up in Boston independently. Waverlys broke up after Perrino moved to Boston, where he formed a new band, the Sheila Divine, with Jim Gilbert and a drummer (name unknown) in 1997. Shawn Sears quickly replaced the original drummer, and three months later, the trio scored a deal with Roadrunner Records.
An eponymous five-track debut EP was issued in 1998 to establish the group's name prior to the 1999 release of their full-length debut, The New Parade.
In late 2000, the band was hard at work on their second album when they added Colin Decker as a second guitarist to broaden their sound. From 1996 to 2000 Decker was singer/guitarist in a band called Lincolnville (from Portland, Maine). At the time he had a day job as a sound engineer, mastering recordings for labels on a contract basis. He got to know the Sheila Divine when he was involved (although uncredited) in the mastering of the New Parade. Lincolnville broke up in June 2000, citing geographical constraints as the main reason. Decker had been living in Boston for some time and the progress of the band began to suffer as a result of the lengthy commute to Portland. Looking for a new band to play with, and not long after his exposure to the Sheila Divine, Decker was introduced to Jim Gilbert at the Middle East, Boston's legendary Rock club. He and the Sheila Divine got together to play and it clicked right away.
In April of 2001 the Sheila Divine released their second album, Where Have My Countrymen Gone, through the Co-Op Pop imprint. Later that year in August, Shawn Sears left the group to spend more time with his child. Following a handful of shows with fill-ins Pete Caldes and Paul Buckley, drummer Ryan Dolan replaced Sears. Like Colin Decker, Dolan is also a former member of Lincolnville.
Unfortunately, Where Have My Countrymen Gone would prove to be the Sheila Divine's final LP. A six track EP, Secret Society, was released through Arena Rock Recording Co. in September 2002. After that they embarked on a non-stop world tour, which would prove to be the band's undoing. While at a show in the mid-west a confrontation with Jim resulted in Aaron throwing his guitar down and announcing to the audience that the band was breaking up. Upon returning home, the band stated on their website they would not break up, but would instead take time off. Aaron Perrino started recording songs in the studio by himself, which would end up on the War Chords EP, the debut release of his new project, Dear Leader (which was intended to be a solo project, but later developed into a new band). The Sheila Divine officially announced their demise on their website in April of 2003, and played two farewell shows in October at The Paradise in Boston.
On December 31, 2005 The Sheila Divine played a reunion show at Bill's Bar in Boston. The band played as a three piece with Aaron, Jim and Ryan.