In 2002, Massari recorded and released "Spitfire" which garnered heavy rotation on Ottawa radio stations. Since then, Massari has been steadily writing and developing his sound. He returned in 2005 with his self-titled debut album release on May 31, 2005 through MapleNationWide/Universal, which sold out nationwide in only two days.

The lead single off the release "Smile For Me" features former Bad Boy Entertainment recording artist Loon. "I'm definitely very selective about the records I get on. It didn't matter if he was an established artist or not, it was just the quality of the record, the quality of the music that made me want to get involved", says Loon about his involvement with Massari and the Capital Prophet Records crew. "I'm very proud to be one of the first Canadian male R&B singers to record with a major recording artist from the States", says Massari. The end result was a hit single that spent 24 weeks on the Top 40 chart, peaking at #18 (BDS CHR) in Canada. Award-winning music video director RT! was responsible for making the "Smile For Me" video one of the most notable debut urban videos by a Canadian artist. The video was immediately added to heavy rotation at MuchMusic, MuchVibe, and MTV Canada. The video received two MuchMusic Video Award nominations for Best Independent Video and MuchVibe Best Rap Video. Canada and the United States were the first to play "Smile For Me", however other countries such as Germany, Australia, Brazil and the UK have begun playing the hit song.

With the release of Massari's much-anticipated second single "Be Easy", the pressure was on to keep the momentum going in the weeks leading up to the debut album release. "Be Easy" received early support from radio stations across Canada and is currently Top 10 (peaking at #4) on the Top 40 Chart (BDS CHR). The video, once again directed by music video director RT!, was instantly added to heavy rotation across the board on video outlets.

For this record, Massari worked closely with Da Heala of the Capital Prophet Records production team. "His vibe is a perfect match for my sound and style", explains Massari. The album draws influences from his Middle Eastern origins. "Because of my background, my music is heavily influenced with Middle Eastern melodies. Over the past few years so many artists are trying to bring Arabic styles into their music, but mine is authentic." Along with its culturally rich sound the album with its upbeat club-style tracks, mid-tempo joints and smooth ballads pays special tribute to the ladies. "My music is made for the ladies because that's where I get my inspiration. You'll notice a lot of the music is upbeat and positive. Women give off so much energy; it's hard not to be inspired by them."

Massari has also been criticised for what detractors say are his derivative and predictable music videos featuring luxury automobiles, cell phones,chin-strap beards, oversized sunglasses, and women who appear to be lusting after him. Critics have accused Massari of simply being more style than substance, and fearful of letting the music speak for itself.