Steve Messina realizes he can come across as difficult. From the audacious name of his band, Blow Up Hollywood, to his roguish inability to stick with one particular style of music, he’s a musician who has consistently followed his instincts. Sure, he’s been reprimanded by some critics and lost some fans along the way, but he wouldn’t change a note.

“I spent many years trying to write hit songs. Trying to get on the radio. All that structure of trying to please the gatekeepers so I could get where I supposedly wanted to get to,” said Messina. “Then you realize you’re not making the music you want to make and something needs to change.”

For Messina, everything changed over a fortuitous three-week vacation in 2001, where he and some musical compatriots sojourned at a Westhampton beach house to drink, swim, dine and collaborate on some new tunes. Messina was musically adrift at the time, unsure what he wanted to do next. Burnt out after years in pop-punk bands, he found himself musically invigorated as the new project started to take shape. By the end of their stay he and his collaborators had dozens of songs. The only thing missing? A name. True to his contrarian spirit, Messina suggested Blow Up Hollywood.

“It was just this idea of… how do we give the middle finger to the industry?” said Messina.

The self-titled debut album was dark and desperate, centered around themes of death and the afterlife. But Messina, who sang and played guitar on most of the record, found that it resurrected his creative spirit. Since then Blow Up Hollywood has become a Messina-led collective of guest musicians and returning core members like multi-instrumentalist Dave Diamond and bassist Steven Bonacio. This has made for some interesting albums over the years. There was 2006’s The Diaries of Private Henry Hill, a concept album based on the writings of a deceased Iraq War soldier. The somber recording was a dark take on the Americana sound enhanced by Messina’s heartfelt storytelling.

Rather than stick with this formula however, Messina pulled a musical 180 in 2010 with Take Flight—a nearly hour-long album of instrumental ambient music with no vocals. He continued in this mindset on 2011’s Collections, an album Messina described as “all over the place.”

All of this artistic whimsy seems to have coalesced in Blue Sky Blond, released this past January. Blow Up Hollywood’s most ardent and concise effort to date, the album is filled with lush orchestration and Messina’s soothing words of love and redemption. It’s another impressive musical transition, but it also reveals the front man at his most heartfelt and honest. His journey thus far has been difficult, but things that are worthwhile rarely come easily.

“It was like a purging,” said Messina, adding that the album was yet another musical journey for the group. “Once you decide to do something you feel like you pigeonhole yourself, but Blow Up Hollywood became it’s own animal. I’m always trying to fight the feeling of being the same as before.”